From Inside Sales Rep to Founder and Enterprise AE with Jesse Woodbury

00:03 Hello and welcome to another episode of Revenue Career Ladder. I think we're on episode four or five of season two already, which is quite scary. But we're to be diving into another career journey of a revenue focused professional to give you insights and actionable tips and maybe even a little reassurance that the journey is yours to define. I'm quite excited about this one because it's a bit more of a traditional sales career path. I think we've had quite a few conversations with people who started in very random backgrounds.

00:32 on cruise ships or as ice skaters. So it's quite nice for us to actually have a conversation about a, like I said, more traditional in inverted commas, because is there any such thing as a traditional sales path? But, um, and there's some really, really interesting stories in there as well. So I'm very excited to talk about the journey from inside sales reps to founder and enterprise AE with Jesse Woodbury. How are you, Jesse? I'm doing great. It's a little early in my time, but, uh, I got up, I got some caffeine and I'm ready to go.

01:02 Hey, I mean, you picked the time, not me. I know. I think this was the latest one. We're across the pond from each other. So I think this was the latest time you could go and the absolute only time I could make it. So that wasn't too early, but all good. Yeah. I'm an early riser anyway, and it's no big deal. I'm always happy to come on and talk about sales careers. How early is early? It's 8 a.m. my time. It's not. I start work at 8 a.m. anyway. Yeah.

01:32 It's early, I mean, it's not early to start working. It's maybe early to get on the air. Uh, cause my peak, you know, air time for a podcast is probably like 10 AM, 11 AM, just when I'm already awake, I'm already, you know, rolling. But that said, I'm, I'm, I was up a little earlier today, went on a quick run and here we are. Well, I apologize for the lack of a lion. Um, hopefully it will be worth it for those watching and listening. Okay.

01:59 we typically start with your first ever role, which actually, interestingly for you, isn't the normal like paper round or fast food restaurant like we seem to have had from Maine. Well, probably more so the UK cohort seemed to start with slightly illegal jobs at the age of 12 or 13. But it's quite interesting that yours was actually as an inside sales rep. So tell me about your first ever job. Yeah, actually, before I get into that, so I'll just say that

02:28 When I filled out my background to come on the show here, I started with my first sales job or my first career job that was after I went to school. I had a bunch of odd jobs since I was 14. I worked in a cafeteria at my school when I was 14. I sold pest control door to door here in the Phoenix summers, which is very hot desert summers, sold door to door pest control. I worked in a really sketchy call center.

02:58 right after high school. And that was actually also a sales job. I don't look at it as like a sales career job, but I look at it as like definitely learnings. And this was, you again, right out of high school, we were selling yellow page ads. This would have been in the early 2000s when that was, you know, the internet was this new exciting frontier for advertisers, right? So had a bunch of odd jobs. And then I actually spent three years working in a bank as well. That that's how I paid my way through school. But then post-graduation,

03:27 I was, set my sights on getting into sales and then later tech sales. And so we'll start with my first sort of selling role was, yeah, was this transactional role for a company, an e-commerce software company. And when I say transactional, that's just a contrast from more of what I do now, which is much more strategic and focused on helping enterprise brands find the right tech solution. This was a, I think $99 a month software platform.

03:56 And so the sale was very fast paced. was, you're trying to close someone on the first call, you know, theoretically, and I shouldn't say theoretically in practice, I was able to close multiple deals a week. Typically, uh, know, theoretically you could close 10 a day is what leadership thought. So very fast paced, lots of dials from the very beginning of that role. It was very much, you're to make a hundred plus phone calls in this role because you're calling into small businesses.

04:23 And these are people that were trying to help get their products onto a shopping cart, very similar to like Shopify. And so was just, you know, smile and dial at the time. It's hard to believe that this world existed when I look back, but there was no, I didn't have outreach IO or sales loft or HubSpot sequences or anything like that to go off of. was all just, you know, I hate, I hate this story, but I'll share it. We would load up.

04:52 a thousand emails into like the BCC line of an email body and then ship it. And then I would have an auto responder set up on the email that would say, if you want to go ahead and just make a purchase, here's a link to do that. And I would still get commissioned if people made a purchase and I would send those out maybe every other week, just this big blast. And sometimes it was probably 5,000 people that it would go out to just total spam, honestly, hindsight's 2020.

05:19 And then my auto responder, if anybody was interested in buying it after hours or something, they could go through and make the purchase. yeah, smile and dial, sending high volumes of emails in a BCC line, not using any kind of efficient tool. And then I always tell that in this role, when I got there, I think we used Salesforce, we had a CRM, but our team was the acquisitions team. We were trying to acquire.

05:44 new businesses that weren't inbound leads or they didn't have any sort of lead score or anything like that. So I think my first week in the role, the director of sales gave me this spreadsheet that had like 10,000 domain names in it. I think someone had ripped it from like the Whois network, which is like the domain registrar and basically said, all right, here's 10,000 domains. I want you to go through every one of these and see if you can figure out how to call the person that owns the domain.

06:10 Some of them were just complete junk or there were people that were just squatting on domains. And yeah, so it was, was kind of a grind. I learned a lot in the role. Uh, was, it was an excellent, you know, kind of intro to tech and an intro to, selling solutions. So yeah, that was my first, uh, first ever sales role. Before I, um, before I asked you a couple, couple more questions about the nitty gritty of that role, you, you mentioned that you.

06:39 came out of college and you wanted to go into sales. What was the thinking behind wanting to go into sales? I only ask because not many people choose to go into sales. They are either forced into sales because it's a widely available job or they fell into sales in that they applied for something that was kind of positioned as something else like business development and then they realized it's just cold calling. how come you wanted to go into sales?

07:08 Great question. So actually I initially did not. I studied journalism in school. And by the way, I had no intention of ever being a journalist. It just looked like one of the fastest ways to get a degree and had the most interesting classes. love that. Yeah. Had some interesting classes. Like actually when I looked at the curriculum, it was really well-rounded. It was a lot of writing. It was a lot of reading history. It was a lot of understanding business and economics. And so that was the stuff that interested me at the time. My goal was

07:37 All still is. And, and, you know, I've executed on that with sales players, my company, but I've always wanted to be an entrepreneur. And so when I was in school, it was, I'll get this journalism degree and it's going to give me this really, you know, well-rounded skillset. can write, I can do marketing, I can do public relations, those sorts of things. understand economics. Uh, so I got a nice well-rounded education, but then when it came time to graduate, I wasn't ready to start a company at, that age and just didn't have any ideas either, frankly.

08:07 So it was like, okay, what do I do now? And for a long time, I was like, I'm going to go and be maybe a project manager. I'm going to go work in some kind of a digital agency or a marketing firm and do, you operations. And I tried to find a role doing that. And I remember I actually had a professor who I stayed after class and I was just picking his brain because he was an adjunct professor, meaning by night he taught classes at the university, but by day he was an executive at a, at a digital agency actually.

08:35 And I remember he said something that was really impactful. He said, you know, you should really consider sales. And my first thought was, ugh, like door to door sales. Like, what are you talking? I've done that. I used to do door to door pest control sales. Like that sucks. I wouldn't want to do that my whole career. And he said, no, no, no, I don't think you're understanding what I mean. I'm talking about B2B sales, selling to companies, selling solutions. It's totally different than your door to door salesperson, you know, smile and dial cold collar and trying to sell something that to consumers that they don't need, right? This is...

09:04 selling solutions to businesses and I think you'd be pretty good at it. And so after that conversation, it really put me onto, you not only will this help me in the long-term on an entrepreneur, on an entrepreneur career path, but it will, you know, it'll help me learn a skillset that can pay my bills in the meantime. So after that conversation, that was my senior year of school. I really set my sights on, all right, how do I get into business to business sales, not, you know, consumer sales, but how do I go sell things to companies?

09:33 Interesting. Yeah. Cause I, that people who don't know, um, SAS sales or tech sales and have never worked in an industry that, um, sits beside it or is involved in it will always see car, uh, always see sales, uh, as car sales, right? They will always see it as a slicked back, uh, discount on payday, you know, car salesman that's snake oil. That's the perception is always going to be that I think.

09:59 It's certainly improved over the last few years, which is really, really good to see, but it's highly strategic. So it's interesting that back in what, do you say 2000? Uh, this was 2012, 2012. Okay. 2012, even, you know, back then to have someone who was an exec at that point saying, no, no, no, it's, it is far more strategic and there's thought and strategy behind it, which is, which is good. You, also mentioned, um, in our conversation previously that

10:27 It was an opportunity for you to move as well. So where did you go to college and where did you end up moving for this role? Yeah, I am. I'm from Arizona originally and grew up here, spent most of my life here, went to school here also just for us in the States. It's all about the in-state tuition. So just found the cheapest way to get through school as possible. Unfortunately, I wasn't a great high school student, so I didn't have any scholarships or anybody funding my education. I had to pay for it all out of my own pocket.

10:55 Uh, but I didn't want to stay in Arizona forever. Uh, in fact, at the time there really wasn't a lot of tech, uh, tech companies here. And it's funny. I remember Googling. What are the highest paying business to business sales roles out there? And, uh, I know medical sales came up. There was pharma was probably the top one. And then at the time I really didn't understand what SAS really meant and what enterprise SAS meant.

11:20 But I knew when I Googled that, that that was what I wanted to do. And so when I started doing more research, it was, you've got to get to a marketplace that has a high density of tech companies. that's, know, San Francisco is not too far away from Arizona, but Boston's on the other side of the country, right? New York was a whole different world from where I grew up. I ended up meeting in the middle because Austin, Texas came up as, there's a lot of tech companies there. That's because of Dell and

11:48 IBM and others have had a strong presence in Austin for many, many years. Now, of course, since then it's really blown up as, you kind of a tech and media epicenter. So, uh, had never been to Texas before in my entire life. Uh, but I knew Austin was where I wanted to go. So I started just putting resumes out there applying for jobs. And that's how, uh, I came across, I think just from Googling and looking at probably Indeed or some of these companies, I found that the, the role that I ended up pursuing.

12:17 did a couple of phone interviews, could not believe that I actually got the job, but it was like, hey, you gotta start in six weeks. And I had, again, was living in a thousand miles away in a different state. At the time, I actually had a one and a half year old daughter. So I already had a family by that time, young family. And so it was moving to a place I'd never been to, getting into an apartment that was totally sight unseen. had never...

12:43 you know, again, visited beforehand. It was just this totally on the fly thing that in six weeks completely changed my life. And when I look back, it was one of the, it was a big bet I took on myself and I'm so glad that I did it. And I've actually since moved back to my hometown here in Arizona to be closer to my folks and my in-laws and my family members. But when I look back, the move to Austin and the, the almost decade that I spent there was totally transformational for my tech career. It was such an awesome opportunity. think it was a bet on myself. It was.

13:13 I have to be successful in this because I'm moving myself and my one and a half year old daughter and my wife across the country, a thousand miles away to go start into this business. And I just have to do, I have to succeed, right? I got to make this all work. So there's a lot of pressure, but it was also just a really cool bet that I took on myself in the career. how old were you at the point at which you made that move? I think it was...

13:39 So I went to school a little later than most people. took some time off after high school and worked and things like that. So at this time I was about 27 years old. Okay. I was going to say, cause like coming out of college, I was like 21 wife, kids moving across the country. was like, that's young. Okay. So 27. Okay. So that's interesting as well, because I had a conversation earlier this week, actually, with someone who went into sales in their early thirties, but even the late twenties is actually

14:08 later than most fall into sales or decide to go into sales. I guess, um, what was it age 27, you moved across the country, one and a half year old. Yeah. Was it, that must've been a hell of a, um, a hell of a period for, like you said, the, the bet you placed on yourself. So what were, what were some of the highlights for you in that first, first role?

14:33 Well, let's talk about the low lights because when I got to Austin, I had miscalculated how much it was going to cost to live there. And we came up short, my wife and I came up short on our, our, you know, monthly expenses or our monthly income the first month or two. And so I was absolutely terrified because it was a little more costly to live in Austin than where we're from. And I had just, you know, made some assumptions about how much I'd be making and I really hadn't factored commissions into it. So.

15:01 I remember one night sitting down, this was a few months into the role, I was making a base salary. I wasn't commission only or anything like that. So I at least had a base salary. There was some money coming in. My wife was staying home with our daughter. And I remember saying, I think I'm to have to go work some kind of a fast food job or something at night. Maybe I'll go swing a sign around on the corner of the street or something. Like got to go find something to do after work. And I remember my wife telling me like, no, I think you should just keep going all in on this.

15:30 anytime you're going to go spend flipping burgers somewhere, you might as well spend that learning sales and getting really good at this and finding the upside that's out there. Go get your money, right? So I'm really glad she had that pep talk with me because I ended up just doubling down. As luck would have it, now I can go on to the highlights. That was a low light. Highlight was around the time of that conversation, they hired a new director of sales on this team who was a guy that had sold

15:58 He was a bond salesman on Wall Street in the 80s, just a crazy dude. Ended up becoming a really close mentor and friend of mine, someone I still keep in touch with today. And he came in and just really, for whatever reason, gravitated to me. We just hit it right off. We both play guitar. So we had a ton of things to talk about and he could see that I was really passionate. He heard that I had a young family.

16:21 He had also, you know, again, been a Wall Street guy and had a family and was trying to make things work and, came from a similar lifestyle as I had. So we really hit it off and he became my sales mentor and he was just incredible. He had 20 years of experience doing, you know, high transactional, but also strategic sales. He kind of had done both. And so he took me under his wing. And then within a few months of that, I was making some pretty big commission checks, which was awesome.

16:48 Uh, and then I didn't have to worry about going to work fast food or doing any kind of night job or something like that, driving Uber at night or anything like that. It was, uh, start, was starting to make those commission checks and then the living got a lot easier. So in terms of the, um, base, if you don't mind me asking, what was the base at that time? And then how much commission were you, did you end up making? People don't believe me when I tell them this, uh, because I talk a lot about this stuff on my podcast and

17:15 At the time, the base salary was $38,000. And then they told me, if you do really well and you hit your quota, you'll probably make another 30K max. So it wasn't, this is not a super high paying role, but it was my foot into tech, right? It was my break into the industry. So yeah, 38K nowadays, I think you could probably start as an SDR in most parts of the US and I'm sure in Europe as well at a, I don't know, 50K.

17:43 45K base salary and then you'll probably have 30 or 40K in commission upside if you hit your targets. I know there's SDRs out there entry level that have a path to six figures. I don't know how common that is these days, but I think it's fairly common. But yeah, looking back, taking a role for 38K, moving to a whole new city with a family, it was a huge risk. And I had some money saved up, but it was not enough. We burned through it. I'm trying to think.

18:11 So back in that sort of 2012, the pound to dollar probably would have been a roughly two to one. divide 38 by two for what that would be in GBP. You're looking at about, yeah, like 18, 19K, which roughly I do remember when I first started at 21, I was fortunate enough to get a job at 24K GBP, which at the time would have been like 45.

18:39 between 45 and 50, but most entry level roles at the time were about 18, 19 K GBP. So yeah, I can appreciate how difficult that must have been. So how long were you in that role? Cause it sounds like you said you had a really, really good mentor. You were learning, you started banking some fairly good commissions. How long were you in that role? Stayed as long as I could until there was too much change and

19:08 As always, this is a theme for anyone listening that's in a revenue career is things are always going to change somewhat. It's good to adapt to some of those changes, but eventually you might hit a point where it doesn't make sense to continue on that trajectory. And so I stayed for about two years, closed some deals, broke a couple of company records. So I ended up closing, you know, multiple deals in a day on one occasion. Just had a lot of fun. And again, I wanted to stay as long as I could to keep learning from this, this manager mentor that I was working with.

19:38 But at a certain point, the company started to have some financial issues and things like that. And this mentor of mine said, you ought to really look to, you know, set your sights on the enterprise. And again, I was still learning what this all meant. It was so overwhelming. I was just trying to pay the bills and he goes, you'd be good at, you need to get on a path to get into, you know, enterprise facing roles. And so I started doing, you know, homework on that topic, right? How do I develop some executive presence? How can I learn?

20:06 the art of reaching out to an executive in a company and getting a meeting and getting, you know, traction in a project, right? And so from there, and I can kind of go into my next role, which was, I was actually at my desk one day at this job, at this inside sales job, and a recruiter called me on my desk line. It was insane. And she's still a friend of mine, actually. She's someone I've kept in touch with over the years. She's probably the best recruiter in the industry.

20:31 Uh, but she, she called me on my desk line. had the tenacity to call me. I'm sitting in a cubicle, you know, a few feet away from this manager and she's like, Hey, uh, is this Jesse? Yeah. Yeah. What's up? I've got a really interesting opportunity for you. I'm a recruiter and I'm working with a startup here in Austin. They're looking for someone like you. And, you know, I was like, Hey, look, I'm going to have to call you back. I'm sitting like five feet away from my manager. So can I call you back another time? And I got her information.

20:59 Ended up going through an interview cycle with her. She had been hired as a, as a recruiter headhunter for, to help build a, S D an S D R team actually, for a very early stage company in Austin. Uh, this company was in the Martech category. So they were selling a software product that was geared towards retail brands. They had some interesting customers, some big box retail brands like, uh, I think Macy's was a customer and a handful of others. So.

21:27 I ended up getting into conversations with her, met with her a few times, met with the team at this startup and what really drew me to the role. And so this, this is really interesting for listeners because this was me being in an inside sales closing role interviewing for an enterprise SDR role. So a lot of people at the time told me, well, wouldn't you be taking a step back if you're going from closing deals right now to no longer closing deals and only focused on building pipeline and meetings.

21:56 And in my head, said, well, what matters is the skillset. This is selling to, you know, small mom and pop shops over the phone, trying to do one call closes. I want to learn how to write an email to an executive and have them respond. And that's what this role that I'm interviewing for is. So I ended up taking the role. had a good heart to heart conversation with my mentor and manager and said, it's time for me to go and pursue an enterprise facing role. And this is my, this is my segue into that.

22:25 is if I can go and learn how to build pipeline against enterprise execs and leadership, then I think I'll be able to get to where I ultimately want to go, which is selling strategic deals and spoiler alert, I made it. So this was a good bet. It was a bet for sure at the time. And again, a lot of people thought, why would you go be an SDR if you've already been closing deals? But I just remind listeners to think about, you know, what is it that you really want to do and what's the end game and what are the skills that will get you there?

22:55 sometimes the path to get those skills isn't perfectly linear. Sometimes you have to take maybe a step back or what feels like a step back. And the reality is this role paid better, even though it was an SDR role. And I'll give you the numbers because I'm an open book, but I think it was like a 55K US base. And this would have been 2014, 2015 around that range. So this is a while, still about 10 years ago, but 55K base. then this one had a much more aggressive commission plan since it was coming in.

23:23 Uh, the founder or sorry, the CEO of the company had been a chief revenue officer at a IPO company in Austin before. So he had a super aggressive plan where he wanted me to double my base and in commissions, there was a huge stock package, which, cause it was an early stage company. was the first time someone gave me, and I was like 30,000 shares in the company. And, uh, yeah, it was a really interesting role. And actually I can get into more of, uh,

23:50 you know, more of kind of the acceleration and what I learned in that, in that role. But I want to pause and make sure you don't have any questions. Yeah. No, I was, I was just going to ask you, went in as an, well, one, uh, what did, what were you selling? You said MarTech. So what was the exact sort of solution that you were selling? You went in as an SDR was that, um, well, I guess we'll talk about your trajectory in that particular company when we do the, the, the learn and stuff, but.

24:19 You went in as an SDR. What was the solution? Yeah. So was an enterprise. Um, it was actually like a marketing email software. If you've ever been on a retail brands, and this is not new technology anymore, but at the time it was, it was pretty cutting edge again, over 10 years ago. So if you've ever shopped on a big brands website and then, you know, you put stuff in your shopping cart on that site and then you leave, you close your browser and walk away. You usually get an email in the next hour that says,

24:48 Hey, Jamie, you were gonna buy these socks from Under Armour or whatever. Did you still want these? We'll give you a 10 % off if you do it right now. That's one example use case, but basically we call it triggered emails. So anytime someone's browsing and then we would do things like capture feedback along the customer journey on the digital front of the e-commerce store. So it was a super, you know, this was only sold to essentially the big box retailers here in the US. So again, their customers were like Sam's Club here in the States.

25:18 I want to say Men's Warehouse, was tailored brands was one of their clients. had like Finish Line, the shoe store as a client. So a lot of like really big, if you walk around a mall in the US, you recognize some of these companies. And that's more or less how I source people was like, all right, who's here at the mall that has enough money to spend on this? And it was a multi six figure investment for the company because there was also a big service element to it. We would install the Pixel or whatever, the...

25:47 the snippet of code on someone's e-commerce site, but then we would also have a team that would help them optimize the customer journey and the shopping experience and provide those triggered emails and those sorts of things. So pretty, you know, custom, very solutions oriented product. And, and yeah, so, so in the role, I was working for their head of business development, who's an amazing woman.

26:10 She was also a really fantastic mentor of mine. And she was at the time, this is such a great story because this is about 2015. She was like one of the first people to go viral on LinkedIn for her content because she wrote this LinkedIn post about how she got 50 % response rate from in-mails. And that went super viral on LinkedIn.

26:32 I'm pretty sure LinkedIn pumped that up too because they wanted to like plug Sales Navigator, which was relatively- we can blame the amount of emails we get now on that viral post. 100 % because LinkedIn took it. actually, LinkedIn invited her to their annual customer conference and she ended up going on stage. It was insane. And so it's funny. So she was an awesome mentor.

26:58 really great to work for, taught us everything. This was a small team I was on, taught us everything she knew about reaching out to executives. And she had an amazing executive presence. She had been doing this a long time, but then she went viral on LinkedIn and she quit because she had just so many revenue leaders banging down her door and saying, work for us. We saw your article about how you use LinkedIn. We want you to come train our team. She actually went and did her own consulting business for a while because she had so much demand from...

27:25 all of the big sales teams were calling her saying, we'll pay you 30 grand to come out here or whatever and train our team on how to do social selling. And again, this is 2015. It's all a really novel concept at that time. Not a lot of people were using LinkedIn for sales or B2B sales before, I don't know, 2013 or 2014. So this was still pretty new. So when she left, the VP of sales and the CEO tapped me on the shoulder and said, hey, we think you should take her place.

27:52 So that was a really interesting move. And this was after seven months or so, it's just grinding the phones and being a regular old SDR rep. I was suddenly being asked by the leadership to step in and be a team lead for my peers who I'd started with, by the way. Four of us started at the same time. then, next thing you know, I was actually the team lead and was working with the marketing department. And I was working with the executive team, worked with our operations team. And that was just an amazing opportunity because

28:22 Also that CEO for that company, he had had just this insane career in tech himself. Like I said, he had been at an IPO company in Austin. Uh, and he was so generous with his time. He would give me a lot. We were in the office together too. So we were in Austin. We're in this tiny rented space, uh, in the West part of Austin, if you know the area. And he was super generous this time he would, he would sit down and, and, know, give me advice on investing and things like that. We would talk about startups.

28:52 I really look back at that time and say, wow, that was like no MBA program, no other, you know, there's no other way I could have learned some of these things. This is like, this is from a guy who grew a company into the, hundreds of millions who had raised $40 million in funding from VCs. And he was opening up his playbook to me and just gave me like a ton of value, just always wanted to have conversations with me. And these conversations would just be like a Friday afternoon.

29:20 We just be in the office and we crack open a Shiner beer. And he would just say like, yeah, what do you want to talk about? And for me, it was like, well, how does, you know, what does it, what does a series be? Like, what, does that work? And what are the terms and what's dilution and you know, what are all these things? And so that was really my bootcamp in, the startup world and what got me really addicted to being in early companies. Cause it felt so cool to, to matter. It felt really awesome to be a key player on the team in such an early stage growth company.

29:49 where I had access to the CEO, I had access to the founders, I had access to all the executive team, and that was just super cool. I don't know if I'll ever get that experience back, and I talk about this a lot on my show, that for people out there who really wanna fast track their career, go try to find something like that. It's harder to do in the post pandemic era because we're all on Zoom calls now and we're not so much in the office together, but whenever you can, if you have an opportunity to sit 15 feet away from your CEO,

30:18 and that CEO happens to be someone who's been at multiple exited companies and has grown teams and scaled companies to the hundreds of millions. Try to take that role and just from osmosis, just sitting there, you'll learn a ton about business. One example is he would invite me into the board calls and he would say, don't say anything, please, you're not supposed to be in these, these are virtual calls. And this was again, pre-Zoom. So there'd be like a...

30:46 like a little phone apparatus or whatever in the middle of a desk in a room somewhere. And the, you know, the board members would all dial in, nobody was on screens at the time. And so he'd like, you you're not here, right? So just sit in the corner, but you can listen to what we talk about in the board meetings. And again, I don't know how else to get an experience like that. Like no classroom is going to teach you that. And even in a big company, you're not ever going to get exposed to how those sorts of things work. So.

31:11 I am a big advocate of people at least trying out a startup at some point in their career. I know it's not for everybody. A lot of people prefer to be at the big established companies and they like the perks and the structure of a larger firm. But if you're someone who's just even remotely curious about what it's like, just go try it. You've got nothing to lose because even if it doesn't work out, the next company will look at that experience and say, hey, you know, that candidate had enough courage to go and join a startup.

31:38 And that says something, right? They must have some fire in the belly. They must have some ambition, probably worth looking at. So I'll pause there. Yeah, no, I was, uh, most episodes I'd say, um, that we've had so far. we've recorded, I said, about 14, 15, um, working in the startup world has, come up and it's only been really in a positive light overall. Like, okay, there are some negative stories about.

32:07 workload and stress and awful managers, but they're very, uh, that I would definitely say that the positives far away than negatives. I, I, I'm at scale up now. So the difference sort of scale up, but I spent two and a half years at a startup before that. And it was the most I've ever learned in 10 to 15 years of my career. Like two and a half years is basically five years. Like you learn twice as much as you would in a legacy, much larger legacy company. Um,

32:36 And I think, it's very interesting what you said about finding a manager like that or a founder or a senior lead like that. Very, very rare. But we had, we've had a few people say similar things of like, when you find a good manager or a good mentor, like that's so rare, make the most of it. Like either follow them in their career and if they move, you go with them. Or you just absorb, like you said, like you.

33:05 You wanted, you asked questions, you were curious. And I think curiosity is another very, very strong trait. So very, very interesting. Okay. So how many, at that point, like when you had the tap on the shoulder, were in, you're only in sales, like what, three and a half years, something like that? Yeah, probably. It might've been less than that, like two and a half, maybe two, less than three years for sure. Okay. So you were,

33:30 thrown in at the deep end, amazing opportunity, and it sounds like you took it in your stride. So what did you learn as a very junior team lead? Ooh, so many lessons. Where to begin? I actually think a lot of people fall into the trap of when they get some authority or power in a company, they tend to take the ego, they have to check their ego a little bit.

33:58 I actually think I approached it from like a servant leadership thing. I didn't want to come in and especially because these were my peers and I was getting promoted to lead peers. I didn't want to come in and rule with an iron fist. That wasn't my plan. I kind of took it really slowly, but some important lessons was like cross collaboration. know, leadership for leaders out there, you already know this, but it's so important to...

34:26 work with other departments and not silo yourself and your organization. So I learned how to interact with our marketing team and our finance team and our implementations team and other parts of the business. so that I had to, I had to actively invest in that, right? I couldn't just sit back and wait for those people to reach out to me. I took charge of that and said, I want to be integrated in with the rest of the company. I don't want us to operate in a silo, even though that company was also distributed, even though we had a small office in Austin, there was team members all over the country and world.

34:56 And so I made a point to have one-on-one calls and do sessions with other department heads and things like that. That was one sort of important lesson. I think the other big lesson that I took though, also from this role that I talk about a lot to my audience and to my coaching clients is don't sell yourself short. If you're going into a leadership role, you deserve to have a lot of skin in the game in a company. And in this particular role, no bad blood or anything like that, but

35:25 They made me team lead, which didn't come with any kind of pay increase despite my absolute need for that. By that time I was having my second child and absolutely needed some extra money, but they still paid me like a rep, but I was doing a lot more work. I was spending at least another 25 hours a week. I still had to carry a quota too. So I still had to carry a territory and a quota, but I also had to deal with all the internal meetings.

35:53 managing department stakeholders and things like that, planning meetings, those sorts of things. So I more or less did that work for free. They gave me some extra equity. Newsflash, that equity turned out to be worthless in the future. Just, again, hindsight's 20-20 at the time. It felt generous because I was running some calculus in my mind that this equity would be worth, I don't know, a million bucks or something. Unfortunately, when the company was acquired,

36:21 They couldn't pay out on the common shares of the stock. So everyone who had equity in the company got hosed. Unfortunately, it is what it is. Wasn't what I think people wanted, but I think there's a lesson in there, which is, you know, take, get paid what you're worth. If you're going to get into a team lead role, don't do it for free. Don't do it for paper options, paper equity, because those are, you that's future state and you don't really know what that is. So for over a year and a half, I basically worked

36:51 you know, for free on being a team leader. It did come to a head. had a conversation that actually was in a bar and I made sure our VP of sales had enough light beers in him. And I approached him and said, you got to start paying me like a manager. I've got two kids now. I'm trying to buy a house in Austin. This is ridiculous. I'm still making the same as my peers and I'm doing way more work. I'm putting in way more hours and he understood. And I think within a week of that conversation,

37:19 He remembered it and he didn't have that many beers. He remembered it and came back and said, all right, we're going to bump you up. so that that bump got me from like 55 or 60 K up to like 75 K base salary. And then they paid me like an MBO or a management by objective bonus. And then they, they threw more equity at me again. At the time it felt generous, but in hindsight that equity ended up being worth zero.

37:46 And a pretty generous comp plan. So they made it right, but it did take almost a year and a half to get there. So that may be not the lesson you were hoping for with kind of a manager role, but I think if you were gonna get promoted and step into a team leader, a management role, advocate for yourself and realize that the company should comp you for that extra investment that you have to make in the day to day, in the people, in being a leader. And so that, yeah, that's kind of was my...

38:15 Fairly brief journey in leadership because as I'll get into later, I bounced back into just being an IC and I've been an IC for the most, know, for at least the last seven, eight years of my career. Well, you know what? I do think that is a very, very valuable lesson because we could have spoken for the last five or 10 minutes or end up speaking five or 10 minutes on. I learned how to communicate with my team members. I learned how to build a...

38:42 QBR deck, you know, all that sort of stuff, which everyone's going to learn as they progress through their career. it's. I understand completely the lesson learned because at the previous company I was on about the startup, it was a package that was a lower salary, but it involved shares and then I did exactly the same thing. You're like, oh, God, well, if we hit the five year plan that they've said we're going to hit, I'm going to I'm going to have 750 K.

39:11 I'm going to be like, oh, amazing. I can buy a couple of houses. come, I can rent them out. Imagine life's going to be great. And then you actually get there and you realize that in order to hit that five year plan, you would have to be one of the most successful companies in the industry and become a unicorn, blah, blah, blah, blah. And as you settle into the role, you begin to understand that that's a night on impossible. Very, very unlikely. So that is a very, very good lessons learned, I think.

39:37 knowing your worth and understanding what the market rate is for a role, not necessarily like the top end of a market rate, but be realistic, like medium or bottom end, at least know the salary band so that you're not getting shafted. And there is always this balance of you have to do the role that you want before you actually get it, right? But you had done it for a year and a half and then it came. that's, I do think that's some very, very valuable advice there.

40:06 I was just gonna go there because people ask me this all the time. Well, then, Jesse, hearing that story, should I have just not taken that role? No, 100%. I'd always go back and do exactly how I did it. Maybe the only change is I would have had that conversation at the bar a lot sooner and said, hey, look, I'm trying to grow my family. I'm trying to buy a house. That actually is neither here nor there. The reality is I was being paid well under market rate for more responsibility and...

40:35 leadership just didn't want to hear me on that at the time. And I think they were cash sensitive as all startups are. That said, startup or not, you know, got to pay your people what the market rate is or as close to it as possible in order to make sure to retain talent. so, unfortunately, they lost me shortly after that too, because by the time I had the two years of leadership experience in the inside sales realm, I started having recruiters knock on the door with some much bigger numbers.

41:04 uh, that were more aligned with a manager salary. And so that made it really easy to say, well, look, the market's saying I'm worth this. And if you're not able to pay this and it's just time to move on. Um, and as much as I love the company and the culture, and I'm getting a lot of mentorship here, perhaps I've hit another ceiling and I, it's time to go move to a different place. But yeah, I think if I were to summarize the lesson too, in leadership, it's learning how to have really hard conversations. And I probably put that off too long. Again, I could have

41:34 had a tougher conversation with my leadership and said, Hey, it's time to compensate me for what I'm worth. And then, you know, having hard conversations with your teammates and your peers and the people that report to you that those are also, it's a skillset. really is. I was just about to say that for those listening or watching, you're fairly junior in your role, it's not that you don't have the balls to have the conversation yet. If you haven't had it, it's that you

42:03 haven't ever experienced, you haven't ever been through it, you haven't learned the skill of delivering or requesting, you know, people talk about the positive sandwich, don't they? If like, you start with a compliment, you say what you really want to say in the middle, then you finish with another compliment. There's all these little tactics and skills that you can use and you do learn over a decade, 15 years, in order to have those difficult conversations. And then when they come up, you're like, oh, it's just another one of those conversations I've had five times before.

42:30 But don't worry if you've never done it. It is daunting. can be, uh, it can be one of those things where you get anxiety because you're like, Oh, well, if I have the conversation and they laugh me out of room and they could just fire me. Like, course these are natural feelings. Um, but yeah, some very, very good, uh, very, very good advice there. And that segues gives us a nice segue into the next role, which is you were kind of in that role for two years. You were getting tapped up because of the experience you had as a sort of more senior leader or a manager in.

42:59 that particular field. So what was the opportunity you decided to go for at the time? Yeah. So I got a call, believe it or not. Another call. Yeah. Another call from that same leader I mentioned who went viral on LinkedIn. So she'd left and this was now, you know, a few years on called me up and said, Hey, you should come join the company. just, I just ended up at, you'd love it here. San Francisco Bay area tech, you know, well-backed company, unicorn.

43:28 They've been around for 15 years. The company's Medalia, by the way, for anyone listening, you can go look into Medalia. Basically, they're in the customer feedback and survey categories. Customer journey is I think the formal term for it. And by the way, this was also my entry point into the niche that I'm in now, which is customer experience CX software. And it's kind of full circle for me because I started my career as a call center agent and now,

43:54 I sell solutions to call centers and still do. Right. And so Medalia was my first opportunity to get into the CX space. They compete with companies like Qualtrics and SurveyMonkey. So surely if you haven't heard of Medalia, you've at least heard of SurveyMonkey rings about it. SurveyMonkey. So at the time, I think they were series E huge, know, 1500 people by the time I joined, totally different than the like a hundred person startup I came from. But, uh, learnings also in going from

44:23 100 person startup, 150 person startup to 1500 person scale up and very close to IPO. They ended up IPOing and just, you they were on a massive tear by the time I joined. So this leader that I'd had called me up and she's like, I'm gonna basically just put your resume in at the top of the stack. I'm gonna highly recommend you. They trust my suggestions here, so you're a shoo-in. And I got the role, which is...

44:50 Again, kind of crazy because they had a pretty high bar for hiring. And I'm not saying I'm a low bar guy or anything like that, but sometimes they overlook people that come from a hundred person startups. you're going to go from a hundred person, you know, series B startup in Austin to a Bay area, 1500 person scale up that was backed by Sequoia, just super high profile company. Usually I probably wouldn't have had a shot at that, but I think I had a good word put in for me.

45:18 And the role was to actually come in and build the inside sales team. Historically, the company had only had a field sales, very enterprise. They would only hire people with like 15 plus years of either consulting or software sales, but they didn't have any sort of transactional motion. And I use transactional now, not like it was in my first role, but still selling to kind of commercial and mid-market size companies. They were used to for their entire life cycle selling to the

45:46 biggest companies in the world. were selling to Fortune 100 companies only at one point. And to grow and to make their IPO lucrative, they realized we're going to have to go downstream. So we're going to have to hire some people that can help us do that. And so my role was to help open an inside sales office in Austin in person. The goal was actually to hire 35 people to fill that office in. That was the project. I came in the first day to work and it was me, one woman who'd moved out from the Bay Area.

46:16 And one or two other people that had come out from the Bay Area with the company and they were like, all right, we're going to fill this whole room. was a big empty office space. We're going to fill this with SDRs and inside sellers who are going to sell this part of the product suite that was more geared towards mid-market and commercial companies. But then we're also going to generate pipeline for the field sellers. So we're going to be calling into Wells Fargo and all these big companies to try to get meetings.

46:42 And that's the role is you're gonna lead a team to do that too. So you're gonna help us grow it to 35 and then you're gonna manage at some point half of those people because we were dividing it by East and West and I owned the West region here in the States. And then we also ended up hiring a bunch of people in Ireland and Germany and other parts of Europe. So the team ended up scaling globally even though those folks weren't in our Austin office, they would come out from time to time and visit us in Austin. So.

47:08 That was an insane role because in a period of six months, I probably interviewed 150 candidates for inside sales roles. So many of them were 21 somethings that were just coming out of school. A lot of them went to really impressive schools. I interviewed people that went to Cornell. And I remember thinking like, holy cow, I went to a state school in Arizona and here I'm interviewing someone who went to Cornell. Why the hell would they want to work in tech sales as an SDR? But at that time, this was 20,

47:37 17, 2018, the industry was really, really taken off and people were saying, hmm, I have a degree from Cornell. Maybe I won't go into iBanking or consulting. Maybe I'll go do tech sales. It sounds like it's just as lucrative, right? And so I was interviewing people just from some crazy backgrounds and CVs. I interviewed a woman who her father was, you a really well-decorated Bay area, a Titan. We had...

48:02 people connected to Mark Zuckerberg interviewing and that was brought up during the interviews is, know, just little note on this candidate that it's so-and-so who's so-and-so who is Facebook's so-and-so, right? And that was always interesting because there was this whole kind of Bay Area community element to it. And for anyone who hasn't worked for a Silicon Valley company, it's just a whole different world. It's a completely different thing, quite different than the Austin based startup that I worked for before.

48:31 a good experience if you are going to be in the tech sector for a long time, it's worth having a logo or two in your career that is a Bay Area unicorn darling company. yeah, I honestly just, as far as learnings, I learned a lot about how to interview and hire and find talent. We hired some insanely talented people, many of which have gone on from being an entry level SDR to now running teams to...

48:59 being strategic reps at some of the top companies in tech. And I am so proud of that team. I called them the Rainmakers. I don't know if any of them are gonna listen to this episode, but you know who you are, the Rainmakers. That was my team of nine people that represented the West region. And they just killed it. Everybody worked so hard. We hit our numbers every time. And that was mostly just because of the energy that we all brought to the job at hand. It was like, let's come in pumped up.

49:27 I was always hopped up on cold brew coffee, because we were in a WeWork workspace and there was free cold brew. So I was always wired and just had a blast like kind of being the guy in charge and being the mentor and helping people learn how to cold call. Some of these people, again, if you're coming from Cornell, you've probably not made a lot of cold calls. You know, you're really smart and you're probably have a really high EQ and IQ, but you just probably haven't done enough cold calls yet.

49:53 And so I was working with people like that. I'm like, oh, let's teach you how to cold call. Cause this is how we, how we do it in tech sales. We're going to call an executive and here's how we're going to write a killer email. That's going to get someone to book a meeting with us. Right? Here's how we're going to follow up on LinkedIn. Here's how we're going to follow people on sales navigator and sort of map out the organization. So it was all strategic prospecting too. It was like, you could sell this product suite into multiple lines of business. There was always like, Hey, we're, we already have so-and-so as a customer. If you go to Medaglia's website, you'll see that they again work with.

50:23 All the large hotel brands, all the large airlines work with Medallia. Actually, what we used to tell people at Medallia is if anyone listening to this goes and searches the word Medallia in their email, no doubt you'll see a bunch of emails pop up because most big companies, Apple, Delta Airlines use Medallia as their feedback provider. So all you have to do is just go type Medallia into the search bar of your Gmail or your email address and you'll see what brands use Medallia.

50:50 because they power the emails that get sent for customer feedback. So cool product, cool team. yeah, man, a lot of learnings. Learned a lot about the Bay Area, scale up culture. I was going say, was this another move then? did you move to the Bay, obviously because it wasn't as much remote back then, was it? No. the task at hand was to build the office in Austin. the goal there, it was just to, it wasn't

51:19 cost efficient for the company to try to grow a team in the Bay Area. So they specifically picked Austin as the inside sales location. They wanted to have a presence there. They still do, I believe, have office space downtown in Austin. So they wanted to have a presence there and they wanted to be able to attract some of the younger up and coming talent from out of school. And Austin was, it still is the place to be. It's a great place for anyone who wants to launch their tech career. So for listening to that, I think,

51:49 That sort of, it sounds so exciting to me, but I know for some it probably sounds like a baptism of fire. Again, being thrown in the deep end, of sink or swim, know, drown or, you know, don't sort of thing, which for me is beyond exciting. Like when you have, when you're faced with that sort of challenge and you've got 40, 50, 60 hours a week and you finish every single day feeling like you've...

52:16 sort of been in a boxing ring like that excites me, but it's not for everyone. But I think just hearing you talk about that role and how much you learn and what you were able to achieve in that period, I think it just goes to show like if you're able to kind of stick it out and I say stick it out, which kind of feels like a negative phrase. But if you're able to, if you're able to just roll your sleeves up, get muddy and just roll with it for a couple of years, it's an amazing like, I don't know.

52:45 test bed, it's an amazing place environment to just really, really rapidly learn. It still comes up when I interview, people still notice the logo on my resume and it's a big part of my CV. And, you know, the learnings, the having that brand, the network, working for a company with 1500 employees. And this is important. Actually, I want to underscore this for anyone who wants to work in startups.

53:12 something that was actually told to me by someone at Medallia. He said, this was a guy who was like a Silicon Valley legend. And he was like, you need to spend a mix of your career in startups and late stage. In startups, you'll learn, as we talked about earlier, you're gonna learn things really quickly. You're gonna be involved. You're gonna take ownership in things. Those are all things that are gonna enhance your career. But at the big companies that are, know, 2000, 5,000, 100,000 employees, whatever.

53:38 you're going to grow your network because you're gonna be exposed to just a lot more people in general. And that's teammates, peers, leaders. And so at Medalia, I connected with some of the just top, these are the top people, like the best of the best in the SaaS industry. They had a very, very stringent hiring process. the bar to get in at Medalia is incredibly high. The founder of the company reviewed every single application before they got hired. That's up to...

54:05 thousands of employees, the founder, she and her husband were the co-founders would review every applicant. So they reviewed my little old resume and would write a report on every candidate. And I saw this process because I hired people and I would see her notes and I was like, whoa, the founder is writing notes on an SDR candidate who's 21 years old coming out of school and had some thoughts about how the interview process went. Because we would have to actually record a culture session where we would

54:35 you know, talk about what we were interested in and what drove us and what our intrinsic desires were. And it was insane, man. It was like this hour and a half long. It was a lot like this podcast. It was like going really deep into certain topics, but being very personal and raw. And she would go, the founders would go and listen to these recordings and then make notes about the candidate and then give a thumbs up or thumbs down as to whether we've moved forward. It was a really insane process. Those founders have moved on because the company went public and then it got acquired again by Toma Bravo, a private equity company.

55:04 And those founders have, you know, since moved on, I believe from the company, they may be in some sort of board position. And I actually had a chance to share a taxi with that, that founder once and had a nice 20 minute conversation with her about what she loved about growing a company. And it's funny what she said. She said, you know, it's cool that we're like a 2000 or a 1500 person company now we're growing to 2000. But I miss when it was all of us just in one room working together on this. This was, that was the best part about the journey. I missed those days of just being a small scrappy team that was trying to do something.

55:35 And that's always stuck with me also. so back to my advice and the advice that I was given is you should cycle between big and small companies because you need to grow your network in the revenue business. But also it's great to be part of what, as this founder put it, be in a room together shoulder to shoulder with people building something. So yeah, anyway, I'll pause there. I want to get your thoughts and commentary. Yeah, no, I do know. I think that's why you find a lot of successful founders and entrepreneurs

56:04 want to do it again and again and again because they miss that room, like you said, the sweaty room where your energy drinks long hours, like they miss that startup environment. And when you start to get into the head counts of even three, four, 500, it becomes, I guess, less enjoyable to people who get hit out of that sort of environment. So that doesn't surprise me at all. So how long were you in that role? Good question.

56:32 And to your earlier comment about trying to stick something like this out, I agree. And one thing I wish I would have lasted a little longer in this role. I only lasted a little over a year there. A couple of reasons for that. I was going to say you've kind of positioned that as a, only lasted as if it's a negative thing, but tell us more. Yeah, I'll tell you the whole story. mean, honestly, I just burned out really quickly. You can imagine hiring 35 people, the stresses of scaling up to that extent.

57:02 managing a team of nine entry level sellers. was very, it's one of the hardest jobs is coaching kids right out of, shouldn't say kids, but young folks right out of school on how to cold call and how to effectively reach out to vice presidents of customer service at the largest brands in the world. Yeah, well, one of my good friends actually, was, when I was head of marketing, he was head of sales and he had a team of, think at one point like 18 people. So I was sat next to him for

57:32 the exact thing you're talking about there. And it was almost as if you had 18 children, like 18 little brothers and sisters. And it was like constant questions like, dad, how do I do this? Dad, can you read this for me? And I can really relate because I sat next to it. I can't believe I'm sharing this on the air, but I probably lost 20 pounds in that role because I was never able to eat lunch. I could not physically go and eat lunch because there was just too much to do every single day.

58:02 I leaned out a lot during those years. was living on cold brew coffee. That's it. Black cold brew coffee and water. And there was no time for lunch ever because as soon as I'd get up to go grab lunch, was, hold on, hold on, before you go, I need to talk to you about this thing. Or even better, would be, hold on, before you go to lunch, can I get a raise? I'm going to lunch. I can't have this conversation right now.

58:29 That was an insane role. after a little over a year, I'll be honest, I basically burned out. And part of that was also, I had moved to the suburbs of Austin and my commute was about an hour each way down to downtown in a car. I had two young kids at home. My wife was working from home at the time. So she was juggling her career and two kids and doing all the pickup and stuff.

58:55 they, again, it sounds really crazy in hindsight, because this is 2017, 2018. We now live in this world where everything's pretty remote and there's a lot of flexibility and work from home options. But when I asked for some flexibility, I was told the role is you're here and you're General Jesse Woodbury and you're charging, you're leading the charge and you're in person and you're approachable and available to these inside sellers who are trying to hit their numbers, right? And I don't disagree. think

59:24 I get it. I think that was a fair statement. I was trying to see if I could work from home maybe a day or two a week just to make things a little easier. And the answer was no. The role was to be in this office in downtown Austin and do this thing. And unfortunately, it just wasn't going to be sustainable with my family life and with my commute and just the pure energy that it takes to go and run a team like that. I think the other lesson that I'll share

59:52 I'll hesitantly share here is that a skillset that I still struggle with is managing up. And it's harder in the bigger companies. I think I'm okay at managing up in startups because the culture tends to be fairly, it's not hierarchical. It's a flat organization, right? But in these larger tech companies, there's a lot of layers of leadership. And one of the things I learned in that role at Medaglia was it was probably more important for me to manage up.

01:00:21 than managed down, but my passion was coaching and managing the reps and helping them make calls and write good emails and those things. And I wasn't as passionate about building PowerPoints that were going to get sent up the chain to, you know, some layer of leaders to review. And I took a lot of sort of criticism, frankly, from the executive leadership there because I was a little unconventional. I'm a startup guy. I'm scrappy. And I think they were looking for someone who was maybe a little bit more polished than I was that had a little more

01:00:51 uh, decorum and different things like that. I was, I'm kind of unconventional. I'm an innovator and what I was doing was working honestly. However, sometimes that doesn't matter. Sometimes like raw numbers aren't enough that the leadership also wants to, have a certain culture, uh, or a certain decorum or a certain way of doing things. And I had a hard time just falling in line. I'm not someone who takes orders very easily without some justification as to why I'm taking those orders.

01:01:20 I don't work for work's sake, like I work for an end game. And so there was just a lot of clashing there and ultimately that led to a burnout. So I had to move on. And so I'll just kind of get into to preface my next move. I realized that I wanted, I realized that I needed to spend more time selling because if you now look back at my career, a lot of my career was just doing business development, not actually closing contracts and deals. I was now very proficient.

01:01:48 in reaching out to executives at the enterprise, because I had done that at the startup as well as Medallia. And I had had conversations with some of the top executives in the world at that point. So I was pretty comfortable with my executive presence and my ability to build pipeline. What I still don't think I knew how to do was I like, don't know how to get a contract signed with a large enterprise. Like, what is that process like? And it's funny because I had some conversations at Medallia about possibly transitioning into an AE or a field sales role.

01:02:17 But unfortunately I wasn't gonna be considered because when you looked at my career, was like, well, you've been at some startups, you've done a lot of BD stuff, you sold before, but that was really small software contracts. You're really not qualified to be a field salesperson here. So there's not really a path for you to go into direct selling and relinquish the leadership hat and move into being an individual contributor. So I realized I kind of had to look out the door to go find my next thing. Luckily I had a killer logo on my resume.

01:02:45 I could very confidently talk about building pipeline. And that's really what is super, that's really what matters in enterprise is if you can reach out to people and get conversations started with large brands, you will eventually close those deals. The closing is more just following the process. I just needed someone to take a bet on me. And so I can get into my next role from there. Unless I'll pause that and make sure there's no questions.

01:03:08 No, no, no. I think what I'm enjoying is I don't have to do too much talking. Yeah, this is good. This is good. I'm just sitting back and I'm almost like the audience in this episode, which is fantastic. Okay. So you've given like a really well-rounded rationale of why you made the change, which I think we can all appreciate the reasons for. And as much as I said, like, just try and stick something out. There is a element of common sense. Like don't try and

01:03:37 Don't try and stick someone out if you've lost 20 pounds and if you could continue going, you're going to kill yourself by all means. okay, so what was the, you were sort of a team lead. You had nine reps. You realized that you needed to go and do some actual frontline selling sort of thing. So what was the next position that you went for? Yeah. So I'll dive into basically just started networking, realized that, and it's funny too, cause I had also at Medalia had a conversation with one of the field sales counterparts that I had met.

01:04:07 And he had asked me, said, or he had approached me and said, you're super talented, you've got a lot of energy, you're very passionate, you're very smart. You realize that if you're just gonna lead SDR teams the rest of your career, you're never gonna make the insane money that's available to you in this space. So you should really think about that. So a lot of people at Medallia had these conversations with me saying, you ought to go do sales for a few years and hell, you can always come back. And then by then you might be qualified to be the vice president of sales somewhere, right? Because you'll have both the pipeline, the leadership,

01:04:36 pipeline leadership and closing experience. So that's where I sort of set my targets and was like, all right, I do like leadership. I like leading teams, but I do want to go get some closing chops so I can come back and lead a more advanced team because on my current trajectory, there's no way I'm ever going to get tapped for a VP of sales role, managing people that close deals because I haven't closed enough deals myself. So I started doing some networking. Luckily the market was pretty good at this time. So there was a lot of opportunity. I was in Austin.

01:05:06 there's, you you could throw a rock in Austin and hit like three account executive roles at different tech companies. There was just plenty of opportunity to go around, but I actually ended up making a move that at the time was also kind of questionable. And I guess that's going to be the theme of this episode is like, I made a bunch of bets and at the time people probably scratched their heads, but in hindsight, I'm really glad I did this. So at that time, this recruiter left a voicemail on my machine and said, Hey,

01:05:33 I'm with a Montana based software company. And if you're not familiar with the States, Montana is not necessarily. yeah, that's more cowboys and cows, isn't it? Montana is not known. I didn't know this at the time, but there is actually a huge software community there. But I shouldn't say huge. Huge is relative. It's not huge like the Bay Area or Austin, but it's more people than you'd think working in software. I thought of Montana as mountains and yeah, cattle and cowboys and.

01:06:03 Yellowstone and those sorts of things. But I was so intrigued because, you know, after the first conversation with this recruiter, he said, the founder wants to fly you out here. This is a series B startup. So very similar to the size of the company where I had led the, where I had first gotten put into a leadership role. And again, I was trying to actually go back to a more early company where I felt like I had better access to the leadership and more say in how things got done. So this is a series B company based in, Montana.

01:06:30 The founder was like, come fly out here and come visit us in July, which if you ever get a chance to go to Montana in July, it's absolutely beautiful. Uh, one of the most beautiful places on earth that I've ever visited. So I flew out there. I'd never been to Montana before. Met with the founder, met with the exact leadership at this company, went deep on the product, met all the engineers that built the product. And it was this, this product was actually a, it was a support messaging tool. So basically what it would do was enable

01:06:58 for customer service, for brands, they could use Apple Business Chat, which is a really cool product if you're not familiar, because you can actually text your favorite companies and it's a whole branded experience in your text messaging window. But we also supported WhatsApp and email and chat and those sorts of things. But the whole goal behind it was to provide mobile messaging for your support team so that they could text customers. That way if you need customer service from your favorite company, you don't have to wait on hold.

01:07:26 you can just send a text message and wait for the support agent to respond back with some way to help you. So at this time, it was a pretty hot category. There's obviously a billion companies that do this now, but they were one of the first. And so a lot of brands were jumping on this messaging trend of like, okay, yeah, our support team right now only takes phone calls and responds to tickets or emails. How can we also text our customers? How can we message our customers through WhatsApp?

01:07:54 So cool product, it was an enterprise AE role. And the VP of sales there, the head of sales there, I think he was head of sales at the time, took a bet on me. He said, hey, this guy's been at a really established CX company, Medalia. He seems to know how to build pipeline, which is something that business really needs. We can fill in the gaps on the closing side. Like we'll help him close. We'll help him get stuff closed, that's fine. Let's bring him in, he's got a lot of energy.

01:08:22 culturally he's really aligned. And so I got that role as enterprise account executive at the company's called Quick and stayed there for a couple of years and actually just really excelled in that role. Again, back to where I like to be, which is series B stage startups. That's where I am now, by the way, in my current role. It's my sweet spot is early enough to where I can text the founder and get something. And I do that all the time. And I made some really good relationships at Quick. think the biggest,

01:08:51 Milestone that I hit there though was like it took me a while to actually close my first deal I think it took nine months for me to actually close something So even though was building pipe I was still you know again kind of raw on the like you're just still new on the whole concept of like getting someone to commit to milestones and next steps and so in this role I really learned how to get these commitments from prospects and to work multi-threaded deals, which was

01:09:16 you know, if you're working with the customer service leader, you also want to bring the IT leader into the conversation. You want to bring the finance team, the legal team into the conversation. So I got some really great mentoring from the leadership there and from my peers there on how to do multi-threading, how to do discovery really well, how to manage expectations in the project. You know, hey, in order to go live by this date, we need to work backwards and sign contracts by six weeks ahead of that, right?

01:09:43 And then in order to do that, we need to review all the info secure, know, info sec stuff, and we've got to go through all the legal stuff. So I really learned, and I've now spent many years doing this. Like I'm, I would say, you know, I'm very comfortable in my ability to kind of run these enterprise projects and work with multiple stakeholders and present and negotiate and all those sorts of things. But the big milestone there was I ended up closing the largest deal in my career, which was with a large B2C brand.

01:10:12 And it was ultimately a seven figure, a seven figure deal, a seven figure customer. And it started out as a $10,000 trial, a pilot basically that we put in place to have them test out the software. And then it grew into this just massive deployment. And I got to ride that wave all the way up. so in that specific deal, I made a life-changing amount of money.

01:10:35 which was really cool. So it took a really long time to get to the point where I was like, wow, that's money that'll change my whole retirement timeline and things like that. if you listen to this episode, it's like, wow, he did all these things and ran all these different directions, but it took until being in an enterprise AE role for him to make a six figure commission check and life changing money, right? And so that, after doing that, I mean,

01:11:03 you can imagine the confidence boost you get. What's crazy about the niche that I'm in is that people also heard about this deal because it's a small town once you get out there and you start selling to enterprise B2C brands is they all, a lot of them talk, a lot of them sort, know, glass door between different companies or they revolving door. That's what I'm looking for. Revolving door between different companies. And yeah, so people heard about the deal and I had...

01:11:29 recruiters reaching out to me and people saying, Hey, we heard about the deal you did with this brand. And it sounds like it was incredible and this and that. So that was pretty cool. And that was around the time I launched my podcast was I felt like I had a ton of things to talk about looking back at my career. was in the thick of doing all these, you know, pretty sizable deals again, multiple six figure deals, seven figure deal. And then, you know, commission checks in the high five and six figures, which was just insane for me. Like I'd never imagined making that kind of money.

01:11:57 Um, but it was what I had always dreamed of and just had not had an opportunity with enough upside to do that. And then in that role, I started becoming an industry expert for contact centers, CX and started really building my network and Rolodex in that category. And that is still paying me today because I can still text a lot of people that I met in that role and invite them to look at the product that I sell now. And that is something that I think doesn't get talked about enough is the riches are in those niches.

01:12:26 As they say, if you can start to focus in on a specific category of software or tech, you'll start to build a community and a Rolodex and a network in that category. And then it's going to make it a lot easier to sell because building pipeline for me is actually mostly hitting people up on LinkedIn that I already know or shooting texts out to people that I've already sold to and asking them if they want to take a look at this product that I'm selling now. And since I have built a lot of trust with prospects and I tend to

01:12:55 you know, try to do right by the people I sell to. Uh, it makes it lot easier because I have an authenticity and a trust about me that, people can get behind. Through, okay. Three things. Uh, the question everyone's asking, what seven fingers, what was it? What, what, was the deal size? Uh, so it was, I think it was 1.1. Yeah. It was, it was around 1.1.

01:13:20 And by the way, that was, it was sort of a stair stack up because again, it started with like a $10,000 pilot. And then we sold like a 250K add-on and then like another 250K. And then they came back and said, we want to just renew next year at 1.1 million. And so then for, so over the course of a year, we had to sort of scale it up 10,000 to a hundred K to 250K. And then at the end of that year, my contact there actually called my cell phone and said, Hey, we want to do.

01:13:50 a more well-structured license for next year, how much is it gonna cost us? And so then I just got with my team and said, it'll be 1.1, 1.1 million bucks. And we put that in front of them and that was that. It was easy. They were like, yeah, sure. We're already planning this and forecasting this into our budget. That was something I didn't know about enterprise selling too, is if you can get into like a really good seller champion relationship, cell phone base. Like I was texting my champion there.

01:14:19 And he was calling me and saying, Hey, I need this or how can we do this? And my, manager is asking me for this. made it so much easier to close the deal because I could just text him and say like, Hey, have you signed the docu sign yet? Or Hey, has this person, you know, approved this yet? And that's really a key skill is being able to, to build those championship relationships. Yeah, that's a good piece of advice. I think it's more common nowadays to try and try and make that a good enough connection that you're able to WhatsApp or,

01:14:48 uh, text or whatever that's more common now, but back then certainly wasn't there was, it was a lot more like regular regulations and things like that. You couldn't possibly do that. You had email only or whatever. Um, okay. Interesting. And then from the point of view, I think for those who I guess aren't aware, like enterprises kind of renowned for having a lot more potential, like earning potential, isn't it? Because you have access to the deals that are one point potentially one, one point one rather than

01:15:18 10 K. So I think enterprise has always been this like sought after area of sales to get into. But what I really like, what I can respect is that you left for this role, uh, well you left the previous company for this role because you knew exactly what you needed in order to get to this point that you wanted to get to, or in order to be happier in your, uh, career choice and trajectory, you knew the decision you had to make. And even though you had had a

01:15:44 arguably a good amount of success at the previous role. You were like, no, it's time to move on. It's time for me to go and add another string to my bow so that moving forward, I would potentially be considered for the role that I wouldn't mind. So how long were you at this role with Quick then? Over two years. Yeah, it was a couple of years and hit some big numbers in those two years, which was really awesome. And yeah, had a really good run. Okay then. So you were there around two years, which for me, I always think like,

01:16:13 two to three years, it's a nice sweet spot. You, I said on the previous episode that I think two years is the, for me is the minimum amount of time that you can truly say that you know the job. So you do it for a year. You've only done one cycle of that job. You've only done the things that are expected of you in a 12 month period once. So if you can then do that again in the second year, for me, that's when you truly know the role and you understand it and you know what's expected of you and how to deliver and et cetera, et cetera, et cetera. So two to three years is a night sweet.

01:16:43 a nice sweet spot. It sounded like you were doing very, very well, at least financially. So why did you decide to consider a new role? Was it another, was it another call from a recruiter? That is a big theme. is something I, you know, it's funny because this comes up in my interviews too. Like I've had some longer stints in my career, but I've had some shorter ones. Uh, and people always ask. And a lot of the time it is someone calling up and saying,

01:17:11 We have a better opportunity for you, more money. I'm a believer that if you can do the same job or to try to optimize for your lifestyle and for the earnings you wanna hit. In this case though, it actually wasn't that. I'll be totally honest and say that I have a little bit of regret. I don't carry around a lot of regret about my career. I'm pretty happy with how things turned out. And I feel like I've done some amazing things and I still have a lot of things to do too. But this is one sort of micro regret that I have. think I might've left.

01:17:40 quick a little too early. It's, you might have left quick a bit quick. I left quick a bit quick. I probably could have stayed. I could probably still be there right now selling some decent sized deals. The truth of it is that there was a big leadership shakeup that the company actually merged with another company. And as part of that merger, they brought in some, you know, new leadership from other parts from the other company that were suddenly in charge. And it kind of changed like the culture and

01:18:08 some of the operations of the company. And frankly, I just got a little spooked because it felt like we had such a good thing going. I was doing really well. I was working really well with the leadership. And then suddenly we merged with this other company that I'd never met before. And those people were now telling me what to do. And I probably should have given them the benefit of the doubt because it sounds like they, you know, the waves kind of settled down and things from the peers that I've that still work there that I worked with, they say like, eventually things leveled off and it got back to how it was.

01:18:38 I got really hasty for some reason, I got spooked and just decided to go and pursue some other opportunities. that's, yeah, again, not a full on regret because it is what it is, but I wish I would have given it maybe another year two. And that said, I vested my shares. I'm still a big believer that the company is going to be a big success. I own shares in the company. I actually now...

01:19:03 work with the same sales leader that I worked for there at the company I work at now. It's a small community and we work together again and we're still in touch. And through that role, I actually met my current boss who I report to now. So it's a small world. Once you start to get into your niche, your network will start to pay you some pretty big dividends. And in this case, like I found my current role, which I'm absolutely loving every day of all because of the success I had it quick.

01:19:31 And so that was kind of one of the compounding effects of doing well there and building a network there in that startup and that community. So yeah, a little bit of regret, but it is what it is. And I made the decision, moved on. I made the, think about as much money as I could have made there. Maybe I could have stayed another year or two and made some more, but I also am pretty proud of what I did next and I can get into that as well. Yeah, I was going to say, so.

01:19:58 you felt you might have left a little bit too soon. So what was attractive enough role to pull you away then? Well, and again, I probably left quick in a little bit of a fear that things were going to change and that I was going to get pushed out of the business because of this new guard of leadership. And so it wasn't so much of a, there's a much better opportunity for me as much as I was trying to mitigate risk at the time.

01:20:26 This was 2021, by the way. it's, you know, not like it was in the middle of the pandemic, but kind of, um, the market was really hot in 2021 actually. So this was also, there was just a lot more pay. So one other thing that I'll just mention is that, and this is a theme now in my, my show is for the work I was doing, I also feel like I compensation wasn't fully aligned with what I was worth. And certainly the marketplace was telling me that I say that like, I'm just Googling, you know, what should an AE get paid?

01:20:56 No, when someone calls me and says, you're 40 % under comp for what you're doing, that's a big deal. That's a lot of money at the enterprise level. If I'm making $100,000 base salary and someone calls me and says, wanna pay you $140,000 base salary, then that's a pretty big lifestyle difference. And usually with the base salary, it's also 2X that is gonna be your on target earnings. So that means your commission payout is gonna be much higher too, if you're in a role that's paying 140 base and 100.

01:21:25 and variable. And so the marketplace was telling me that I was under comped and I had brought this to the attention at quick, the leadership at quick. And man, I've had a lot of conversations with them because I still keep in touch with the leadership team there, as I said, and it was just kind of an unfortunate timing thing. And I got spooked and decided to move on.

01:21:47 And what was the role that you, yeah, yeah. What was the role? So also through the network in that same CX software category, I had actually been recruited by the in-house recruiter at customer. That's customer with a K. And they're, you know, basically a CRM tool and a ticketing tool, very similar to like Zendesk or even Salesforce or Oracle are all different, you know, ticketing products. But customer was this, you know, conversation based

01:22:17 CX platform and the recruiter had reached out to me multiple times. It was known that they were being considered for purchase by Facebook Meta, which was interesting. That was sort of out there. It wasn't official yet or anything like that. It wasn't for sure, but there was this rumor that they were going to get acquired by Meta. And I just thought I'd take a chance. mean, the recruiter said like, this is a super hot company. The product's selling really well. The team's killing it.

01:22:45 I was looking for an opportunity to go and sell a multiple seven figure deal. And a team member had just closed a multi seven figure deal at customer with a really large consumer company. And so it just felt like a chance to go and join a later stage company again, build that network out again, and work for a more scale up type operation. So I went over and joined customer and then about...

01:23:12 I think six or seven months after I joined, Meta officially acquired us, which was a super interesting thing. And it ended up being actually a pretty lucrative deal for everybody there, myself included, because when I joined, when I joined customer, they had me sign a letter saying, I acknowledge that Meta is likely to purchase this company. At the time, they weren't even called Meta yet. They were still Facebook. But I have the letter that says, hey, we have an intent to acquire this firm at some point in the near future.

01:23:41 If that happens, here's how many Meta shares or Facebook shares you'll get in the company and they'll vest over this period. And so I signed like a, they called it a comfort letter. So it was kind of interesting. I'd never signed a comfort letter before, which was basically saying like, yeah, I totally understand that this is a company that may get acquired here pretty soon. And I acknowledge that that's a possibility and here's what my comp for that will be, right? So yeah, after I actually had a really great, start at customer two that I want to mention, I came in.

01:24:11 and closed two pretty sizable deals within my first 90 days in the role, which is actually pretty insane when I look back at it. Part of that was because there was an underserved market in the company that I was able to reach, which is Latin America. I speak fluent Spanish. I should have probably explained this earlier in the episode that I happen to speak fluent Spanish. And so when I joined the company, the VP of Sales, he called me up one day and he was like,

01:24:37 you said you speak Spanish on your resume. You don't look like you speak Spanish. Is that all? Is that don't look like you speak Spanish. That's he said. He's like, how do you speak Spanish? You said on your resume, you speak Spanish. Was that all bullshit? And I was like, no, no, no, it's not bullshit. I do speak fluent Spanish. And so he goes, great. We have all these inbound leads coming in from Latin America and we don't really, you we have one person working on them right now. We need more support on this queue.

01:25:02 So I'm going to start funneling you some Latam leads. And sure enough, I got these two deals going, one in Columbia, one in Peru. And I basically closed these deals through WhatsApp because I was just messaging these teams down in Columbia on WhatsApp. And that's what they use pretty heavily down there. And sure enough, in 90 days, I closed two contracts. think one of them was like a 75K deal and the other one was like 150K deal. So not small contracts at all. And I became...

01:25:31 like rookie of the year, something. And then a few months after that, I closed a pretty large deal with a entertainment brand that was just an inbound lead that I happened to get and worked the process and used my playbook of kind of managing the project milestones, secured the contract, and then I became like the rep of that quarter too. So I won a bunch of awards. All during that time, we were getting swallowed into meta or, you know,

01:25:58 moved into Meta as part of the acquisition, which was so interesting because I was working off two computers. had a Meta machine and I had a customer computer and then we had to merge those things. But then prospecting got really interesting because I had a Jesse Woodbury at facebook.com email address. So I was sending outbound emails from a facebook.com and you can imagine the response rate on that is pretty high when someone from facebook.com reaches out to you, you might reply. So that was pretty cool. I think just

01:26:27 One of the lessons there too, in going from my career, mostly in early startups with maybe 100, maybe 200 employees, to Medallia that had 2000 employees by the time I left, to then going to someplace like Meta that at the time I was there had 70,000 employees was kind of trippy. And I don't think I really knew what to do with myself. I just sort of had to focus on the deals I could work on and the small pot of people that I was working with. But I did spend a lot of time trying to get

01:26:57 out of the organization I was in and learn more part, Meta is a huge animal and there's just so many different organizations. At the time it was, Oculus was huge and there's of course WhatsApp. Actually, they pulled me into the WhatsApp side of the business there because of my Spanish abilities. They said, we need you on the WhatsApp API side of things and we're gonna have you run a couple of experiments in Latin America to see if we can get some business that way. So it was really, really cool. And then suddenly it ended.

01:27:27 Suddenly we got a note from the founder of customers saying, Meta's actually decided to carve us back out. And they are gonna, you know, they're gonna send over more instructions later, but for now just close your laptop. And by the end of the month, we'll have some kind of update for you. And so this was like in, I think April, by the end of May, they had officially just kind of cut our team. They basically just said, we're carving the business back out.

01:27:55 and we're gonna lay off anybody that came in as part of the acquisition. Fortunately, and I talk about this a lot, is the Severance, if you ever get a chance to get laid off from a company like Meta or Google or any of these big players, they have pretty generous Severance packages. And I think mine was, was six or seven months, plus I could vest equity during that time, plus I could get my 401k match during that time. And then Meta actually paid me like some kind of a,

01:28:25 like a separation bonus. So I got some kind of bonus check. So they really, you know, they make it somewhat easy for you when you do. So no hard feelings for me. It was just, it was surprising because I felt like we had a really cool product and we were trying to integrate it in with the rest of Meta's business. I felt like we had some traction, but apparently it just wasn't enough with Zuck's cost cutting measures to keep our little business unit inside the house.

01:28:52 I believe Metta is still an investor in the new customer, because customer has now relaunched as an independent company. They've raised more funding and they kind of bought the property back from Metta. Just for my own benefit. So why did Facebook buy customer first? What do they want? They were going after this mission of what they called social commerce. because the interesting thing about customer's platform,

01:29:19 was it was a ticketing tool, like a support ticketing tool, but it was all based on conversations. The premise was like, if I wanna get help from my favorite company, cause I need to return a t-shirt or I need to get support on my account, that should be a conversation and not a ticket. And most companies, it's just like, okay, a ticket opens up when Jamie reaches out and asks to exchange a t-shirt, right? But with customer, you could have a sort of...

01:29:46 Omni-channel conversation with a customer across WhatsApp, across all the different meta channels, also Instagram. And that way, if I need to return a t-shirt, I could just go on Instagram and message my favorite t-shirt brand and say, Hey, this was the wrong size. I need to send it back. Right. I am totally butchering the mission by the way, but just no, no. I have actually used Facebook messenger in that way with some brands. that, yeah, that makes sense to me. Why did they then, when you say carve it back out,

01:30:13 Was it that they bought it and then they were like, we're gonna do our own thing and we didn't need to buy that. Not do their own thing. I think they just decided that they wanted to scrap the project altogether. It's an expensive thing to just scrap, right? It was a billion dollar acquisition. The company was acquired for $1 billion. Again, I personally made a significant amount of money from the shares that I owned. I always tell people...

01:30:41 looking back at my career so far, was the only exit that I've had. How much, like, bullpark how much we talking? It was multiple six figures. Yeah, multiple, not seven figures. I'm not, you know, buying a yacht kind of money, but it was multiple six figures exit in terms of the equity. Not bad for seven months. Right. Yeah. And that's the thing is it was seven months.

01:31:05 And I got to continue to vest my shares too, after this, in the separation period. So I was still vesting equity in Meta, which if you've watched the stock price of Meta since 2023, when this happened, it's gone insane. I think when we left, was in the like hundred and something range and now it's like, I don't know, five or 600. It's gone up to 600, think recently. So it's been a very good stock to own, honestly. And so,

01:31:31 super interesting experience. And I don't regret it though, because it's pretty cool to walk around and say that you have Facebook on your resume. Obviously there's a certain respect for that in the tech industry. It's kind of a controversial company to be honest though too. So there's a double edge to that. But when people hear the work I did there where it was like, hey, we got acquired. We were trying to integrate our customer service tool into the meta channels, Instagram, Facebook, WhatsApp, as part of,

01:32:00 supporting brands that use Meta and integrating the whole, they wanted to integrate the whole experience to where if you see a Facebook ad or an ad on Instagram, you could not only sort of click on that ad and purchase something from an e-commerce brand, but you could also then message them through our platform and have this whole sort of holistic view of the customer journey. So it was a really cool idea that the guy who sold the idea to Zuck had a good idea. He ended up resigning later and that's another story. I don't even know all the details, but like,

01:32:29 You know, he made a good amount of money. It's all good. I'm sure. I'm sure either, either that or he got in big trouble for spending a billion dollars on, on a company and then a year and a half later saying, actually, let's just push these guys out. So yeah, carve out being a divestment. They decided to no longer keep us in house. Fine. Okay. So that, that kind of brings us up to, as I understand it, um, everything before your current, current role, right? Yeah.

01:32:56 Yeah. And we're not going to go into your current role because you're still there. You're still learning. You're still developing. There's probably not enough for us to talk about right now, but what is just to sort of wrap up that portion of the conversation? What is your current title? Have you gone back into a similar role at the next company? Yeah, back. I'm back at a series B startup. Again, this is sort of my sweet spot. This is where I just, here's what I optimized for this time in my career. And some people get

01:33:24 surprised when I say this, but I'm optimizing for fun and lifestyle, but also earnings. There's a lot of upside where I'm at right now. It's a really great product. It's in the AI category. And I'll plug the company where I'm at Language.io. It's a, know, early stage company with an AI product that actually does language translation. So the fact that I know Spanish kind of comes into play with that it's language translation for customer service. So if you're, if you're serving customers in, you know,

01:33:53 Latin America or in Asia, you can speak any language instantly through the power of our generative AI product, right? And so it's a great tool. It integrates in with people's Salesforce or their Zendesk. So it's already in the ecosystem of CRM apps and it's a lot of fun to sell. We're getting a lot of interest from large brands that want to be able to support customers across the globe. And so I joined because it just seemed like a fun team that has a lot of ambition. There's definitely some big upside here.

01:34:21 The lifestyle is not the Bay Area venture funded lifestyle. They're definitely aggressive and hardworking people, but there's a whole nother world when you're going into like a Bay Area, Silicon Valley startup. And this one, this company is actually headquartered in Wyoming. So similar to the Montana thing. I like working for Cal. I'm a cowboy myself. So I like working with cowboys. We go Montana, Wyoming, and they're

01:34:47 There's surprisingly a lot of really talented people. shouldn't say surprisingly, there's, there's big places, right? There's, there's gotta be some talented people there. Yeah. There, there's a lot of talented people in those States in the U S that people don't realize are here. And so, yeah, great product. Um, you know, very generous compensation offer and those sorts of things that the leadership team I work with is solid. And so I'm, very long on staying here. My plan is to stay and keep doing this while I grow sales players.

01:35:16 which is my podcast and newsletter and content business. then, know, someday, I don't know when I actually think that I'll go do that full time. My career path for a really long time was to become a VP of sales or a chief revenue officer. And the older I get, the more my family grows and gets older. And the more I kind of look back at the journey I've had, I think

01:35:40 It would be way more fulfilling at this point to keep doing this and live the lifestyle I live, make the money I make, and then go and launch a consulting company or do something where I'm a solopreneur and can just be in charge of my own destiny. That actually calls me a lot more than being a VP of sales at a venture-backed startup and having all the stress and pressure of that. All that said, if the right opportunity knocked on my door, I would certainly jump back into leadership at some point.

01:36:09 Well, I think this is, I'm glad you mentioned your say it was players stuff. if, if anyone wants to and check that out, um, just before we go into this roundup section of the conversation, then definitely do. And I think it's, I've always had a bit, there's a bit of me that's like, I want to have a, some sort of, uh, some sort of thing for myself consultancy. Um, I don't know. I I'm still, I'm enjoying the role. mean, I'm learning, I'm developing and I kind of want to just focus on that for now, but there's, yeah, there's this little nagging thought at the back of my mind.

01:36:38 All right, round up. So off the back of that good hour and 37 minutes, hour and a half conversation through the career, which honestly has been really, really good because I've not done too much talking and it's been super detailed and I think super honest, is great. What would be your top three tips for career progression, climbing the ladder? You got to actually do the work. You have to do the hard things in a revenue career. That's not a popular take, but it's the truth.

01:37:07 not, not, you know, anytime that I've delivered big deals, big results, done big things, it's because I actually did all the work and it's easy for me to sit on a podcast for an hour and a half and just talk about the last 15 years. But the reality is every single day was, was calls and emails and reaching out to people and doing, you know, challenging work. And that's the reality is you do have to, but you, you, you've done the hard work, which means you've earned the right to sit for 90 minutes and have a lovely conversation.

01:37:38 The next thing- Okay, so do the work number one. Number two. Number two. I've hit this a few times in the episode, but it is so important to build a network, a community, a Rolodex, whatever you want to call it. Let's just call it a network because I think that's the easiest way to think about it. That's not just peers. That's not just the people you've worked for, leaders. That's also, again, I've been exposed to founders and startups. I've been exposed to investors. I've been-

01:38:04 I've had access to partnership opportunities that have put deals into my pipeline through partnerships. I've even had people like Deepak on your team reach out, right? And I've built networks with people like Deepak at Dealfront. so building your network, and it's best if you can do this within a specific niche category. So find out what you like to do, what part of the software business or the B2B business you like to be in, and really start to find out who the top people are in that space.

01:38:34 Start to make friends with them, make a network. Very, very good piece of advice. think I spoke about it on a previous episode, but I think I've actually only ever applied, like I've only ever got one job through a standard application process. There's a job I'm going to apply for it. The rest of it was referrals or people saying, I've got this role, are you interested in it? So that's probably one of the most valuable things.

01:39:02 valuable pieces of advice actually. definitely, definitely make note of that one. And then number three. Yeah, you've got to work with people you like. And this is a theme that probably came out is like the roles where I felt the most successful, where I was the most successful, tended to be working with people that were nurturing my interests and creativity and curiosity. It was working for people that weren't afraid to have some fun. People that were transparent and authentic about who they were. So you really...

01:39:31 have to find that tribe of people at some point. And then you've also got to be behind a product that you can get excited about. If you're selling something right now that you're just not over the moon, pumped up every day to go put out there in the marketplace, then you should seriously rethink where you're at because you won't be as successful unless you can get, know, white hot passion about what you're selling. That sounds really cheesy, but like you have to be pretty damn excited about what you're selling every day in order to hit some of the big numbers. You know, if your goal is to hit a big

01:40:00 commission check, you have to be pretty pumped about what you're selling to do that. No, I think it's good piece of advice. At the end of the day, you're spending 40 to 60 hours a week, probably on average, for a good number of years. You've won, you've got to, like I said, enjoy the people you work with because you'd be miserable otherwise. And you've got to kind of believe or be passionate about the product again. Otherwise, your motivation is going to be really, really hard to maintain. yeah, a nice one to finish off. The career regret one.

01:40:29 I think we've kind of already answered it. I think I know the answer to this, but any regrets? Yeah, really quickly, just to summarize, I mentioned this earlier when I talked about leaving quick, know, try to give your role as much, you know, maybe err on the side of giving it more time. I was sometimes really hasty about jumping ship or moving on to the next thing. I feel somewhat justified in that because most of the time someone was calling me asking if I'd come work for them for more money and

01:40:58 more opportunity and I think that's worth chasing. But also try not to let the day to day impact your decision making, kind of look at the trends over a few weeks or months or even a year. And if you're still unhappy or you still feel like you can find something better than go for it, but that would be the only regret I have is just maybe giving things a little bit more time, being a little more patient. Patience is a virtue as they say and not everything is about money.

01:41:27 trend has come up a lot in the conversations I've had so far. But in fairness, like in your defense, whatever you want to call it, you've touched on it. You had a young family. Yeah. You had a one and a half year old. then you had a second kid on the way and you were at a point sort of thinking that I need to support my family. So money does come into it where, know, it's a balance. Money isn't everything, but if you cannot support and

01:41:53 Uh, support the family, network around you, then money kind of is everything. So it's a balancing use, use a common sense approach. Um, and again, like the next couple of questions, I think we did touch on it with sales players and your sort of goals, but what's the next step, um, for you on the ladder? know you've, you've only been in your current role for, um, a short period of time, but what's, what's next for you? Yeah. Yeah. Great. Great question. So if you remember back to me talking about my schooling and.

01:42:21 early part of my career, I've always had the goal of being an owner of a business myself. And fortunately through sales players, I've launched that as a formal business. I mean, it started out more as a idea dump on a podcast and now a newsletter, but my goal has always been to figure out a way where I could make money for myself and use the sales skills that I've developed over my career to do that. So that's, you know, a little bit longer term because I actually, I'm

01:42:48 I'm getting older, but I still feel like I have a few good years left in me this, in the, you know, venture-backed tech business. And since I know what the upside is in this business and I know how to do the job I've already, you know, learned and having this Rolodex, I want to try to maximize that for the next call it five to seven years. And I hope to stay at this company for five, seven, 10 years and just, you know, keep doing what I do, which is closing strategic deals, working with really cool brands to implement really cool technology.

01:43:17 and get paid very well to do it, right? So that's my, you know, sort of five to seven year timeline is just to kind of stay put and see how this venture goes. But then as I get into my, like, I'm 38 right now, just for listener context. When I get into my- And yeah, you look about 23. That's why I get that a lot. I have a, I do a lot of skincare. yeah, I No, it's those six figure comp checks that are helping. Yeah, I'm not gonna lie. It does help. can-

01:43:46 Definitely investing. of plastic surgery here and there every couple of years to keep you going, you know. No surgery, but definitely investing in like higher quality food. Especially early on in my career when I was paycheck to paycheck, like it's really nice now to buy higher quality food and some other perks like that. yeah, so 38, when I'm in my kind of mid 40s and late 40s into my 50s, I kind of just want to work for myself. I want to have a almost retirement business.

01:44:12 where, and I've met a handful of people that do this, by the way, that they get into their 50s, 60s, and rather than retire, they just have like a business that they run that's maybe like 10 or 15 or 20 hours a week, and they make some amount of money doing that, and it complements their retirement, and that's more or less my goal, is at some point, I'm gonna step away from the venture-backed tech business and just do some sort of consulting or create content full-time through the podcast or something in between that. Nice, okay.

01:44:41 And then again, we kind of touched on this, but I think that's the end goal, Is kind of what we just discussed is. Yeah. I guess next step is just to keep building my skills, to keep building my audience on the, on the media side, because if I am going to run, know, my own service business or consulting business or sales training business or something like that, a key part of that is reaching a lot of people to put in the sort of top of that funnel that can then one day become clients or consulting clients. And so that's.

01:45:11 I do that a little bit of that every week. In addition to my job, I'm putting content out. I'm showing thought leadership on LinkedIn and through the newsletter and through the podcast. And I've already built, since 2020, I've been doing this and I've built a really insane network of sellers and go to market and revenue thought leaders. And I plan to continue doing that for another five years or so until it's hit a point where I've got plenty of pipeline to keep me fed for the rest of my life. Nice.

01:45:39 Well, that brings us to the end of our conversation. This is the longest episode that we've recorded in season one and season two so far. But I think for anyone that's tuned in, whether they're watching or listening, very, very beneficial from the point of view of like, peating together career and actually some real honesty in why you change roles and some really, really interesting stuff of, you know, being purchased by Meta and losing your job after seven months and things like that. Like

01:46:07 It's not all plain sailing. So a very, very interesting episode for me. So appreciate you jumping on and having a heart to heart about the career. Yeah. I think if there's one takeaway I can leave with listeners too is just don't get too hung up on the little things, right? Success is not a linear path for most people. I'm sure there's somebody out there that has a nice linear graph for their career, but

01:46:34 careers, especially in startups, especially in technology, they can get kind of messy. And if you have real conversations like this with a lot of founders and leaders in tech businesses, they start to open up and talk about all the times they've been shafted on equity or have been terminated without cause or whatever. It's very common. And early in my career, used to think like, oh man, I must not be good at this because I'm struggling or I'm mentally struggling or I can't seem to find the path, but stay the course.

01:47:02 try to step back from time to time and look at the skills that you want to develop because those skills and that network that you build are what is going to propel you into life-changing money and new opportunities all the time. A fantastic piece of advice to finish there. honestly, I think that I'm looking forward to sort of writing the show notes and the expect to learn section because I think there's a ton in that expect to learn section. So.

01:47:28 A very, good episode and hopefully those listening have enjoyed it and we will catch you in the next episode.