From Waitress to VP of Marketing with Sophie Buonassisi

00:03 Hello and welcome to another episode of Revenue Career Ladder. Your go-to source for real career stories, practical advice and actual insights from revenue pros who've been there, done that and are here to help you climb towards your dream job. In this episode, I'm joined by Sophie. I'm going to butcher this second name. I'm going to say, I don't even know if I want to attempt it.

00:27 We're joined by Sophie and we're going to be chatting about her journey from waitress to VP of marketing. So before I hand over to you, do want to just tell us how we pronounce your second name? So yeah, bet. You just got back from, you just got back from a Malfi. It's Italian. Yeah, that's worse because I butchered it there. So I love it. It's pronounced Buonassisi. It's definitely a mouthful. Well, yeah, I definitely wouldn't have pronounced it like that.

00:56 I was stuck on the almost like the British way of boy on something like that. Or, um, but that's kind of fun. So kind of like that. Yeah. It's a bit more of a French vibe. I don't know why I read it as French, but there we go. Um, so without, uh, without further ado, how, are you Sophie? I'm doing great. Thank you. Beautiful sunny day here in Vancouver. So can't complain. Yeah. It's, uh, it's sunny here today as well in,

01:22 and for anyone who knows Wales, that's a rarity. So coming back from sunny Italy, I was expecting it to be raining, but I think I've brought the weather with me, thankfully. I love it. Yeah, you're kind of straddling actually my background in general. So I'm half British Welsh and then half, I guess, Italian, Italian through marriage, but I've got another half there, but I've got the Italian and then the Welsh side too. So I love it. And thank you for having me, It's pleasure to be here.

01:52 Most welcome. think it's me who should be doing the thanking because I think the conversation over the next 90 minutes will be based on the notes that I've seen is going to be very, very beneficial and useful for those listening or watching. So I think you're the first person to start the conversation with the thanks. that's a nice touch. Maybe it's the Canadian me. Potentially the British as well, the Welsh, very, very polite, renowned for being very, very warm people.

02:21 Out of curiosity, what area of Wales? So a blend of Cardiff and then a tiny, tiny village, south west, Nanturnus. It's like maybe eight houses in this village, but most people kind of migrated to Cardiff and then eventually over to London. I live in Cardiff, but I've not heard of the tiny little eight house village. That's definitely something I've not seen on the map, but...

02:48 Yeah, I'm based in Cardiff. So it is a good city, albeit I've not managed to get over to Vancouver and I've heard very, good things about Canada in general. So one day. Coming over anytime.

03:03 Right. So we usually start these conversations with the first ever job, which we touched on at the start was waitress or hostess, depending on where you live in terms of what it's called. Do want to just touch on that very, very briefly? Your first ever job? You bet. I technically had a couple others before, like soccer referee and things like that. But I think the waitress and server side was the most pivotal first job and most proper first job, if you will, that I had.

03:32 Um, it, uh, it was a job that really shaped my ability to understand customer service. I'm a huge proponent for service oriented jobs at some point in people's lives. And the reality is most jobs are service oriented now, but some kind of fairly service heavy job, because it just forces you to interact with such a variety of different people and, uh, just develop those skills too, in terms of, of service and better understanding.

04:01 you know, how to support people that are understanding how to work in an organization, if you will, at a smaller scale. So I think it was really kind of fundamental for developing a lot of those early skills I joined when I was about 15 years old. And you mentioned refereeing as well. So what sort of age was it that you were refereeing? was it? Did you say soccer? What was it? Football? Yeah, football, soccer, however you want to call it. was probably about, probably about

04:30 13 years old and I've ref different soccer games or flagged And was that male female mixed? I predominantly did female. I did a couple of male games, but I was mostly on the female side or at a young age where they're mixed. Well, I was thinking, probably out of any job at that age, refereeing is probably one of the, I don't know, hardest in terms of

05:00 in the moment, feedback from people that you're refereeing. let's be honest, it's renowned for people disagreeing with the referees. So that must have been a very early experience of, I don't even know what the word for it is, but just negative feedback based on your decision making. absolutely. I quickly learned that no matter how good of a job you do, someone will always be bad at you.

05:29 you will always be the enemy and that's okay. But it was never a fun position to be in. So I think that's why I decided to not pursue it too, too much longer. did it for a couple of years at a young age before I was more eligible for the restaurant or any kind of other job. But yeah, it was definitely interesting. I think there was a time where I was refereeing maybe five-year-olds, six-year-olds.

05:51 one of the others, one punched each other in the face and one got a bloody nose and then they all scattered and ran away. And so I was running after them and all those kinds of experiences that are all good ones for shaping you. sounds exactly like the SaaS industry, the technology industry, if you ask me. Okay. So we've done your first ever job. So we then move on to, I guess, your first highlight role, which is typically in averted commas, your first...

06:21 proper job, the first job or career move that you sat down, thought about, planned out, whether that's before college or after college. So what is your first highlight, career move or role? Yeah, the first one that I would highlight would really be working in Environment Canada, which was the Department of the Federal Government of Canada and working in public policy and program management. And I mean, I took that role because

06:49 I thought it would be a really interesting vehicle for making impact, especially because it would span nationally. So worked on regional projects and national projects. I was really excited about that. And then this particular role was in a special projects unit, which are designed to essentially address high priority initiatives. they're ones that aren't usually established.

07:16 fit into an existing mandate, they're a newly created mandate. So was a really exciting opportunity to step into something brand new that doesn't have the typical kind of structure that you would in a federal government. So I'd essentially taken a couple people from different areas of the organization, different departments, and brought them together in a bit of a tiger team. And so I joined that tiger team to work on indigenous policy. And what that entailed was actually looking through and reading through

07:45 Manually, this is obviously way before the chat, GBT days, manually reading through indigenous policies. So there's seven different steps in understanding at what stage are they at in their policy development journey, flagging the appropriate kind of tenants that would feed into other departments. So if we had to consult agriculture or enforcement and bring in those folks, I would then flag it in the policy and then I would then liaison, understand.

08:14 what their interests are in that policy, bring them into the conversation. There was also lot of external stakeholder engagement with Indigenous groups, which was fascinating. And I got to travel to a lot of really remote areas of Canada, meet with Indigenous groups and their leaders and, you know, really be welcomed. They were super, super welcoming into their different customs too. And that was a really interesting eye-opening experience of just how different business can look for different

08:43 groups, different areas, different geographies. I'll pause there. Happy to go into any kind of other areas. No, was just going to say, think program management is challenging at the best of times given that you are managing or you're sitting in the middle of loads of moving parts that you're looking after. when I'm guessing with public policy,

09:07 Now this is going to be my uneducated assumptions based on TV programs or films that I've watched. But public policy can be very, well, challenging is one word, but in terms of keeping people happy, trying to get everyone on the same page, bartering, I guess, in a lot of senses of the word. But program management for public policy must have been very, challenging.

09:36 It was a lot of fun. I really enjoyed it. I think it came with its unique challenges. Part of that was just because of the nature of it being a special projects unit. So didn't have the necessary existing infrastructure that you would typically, but it was a ton of fun. I really enjoyed it. Got to build out some new policies, worked with an enforcement branch, for example, to help understand and create a guidebook for them around the customs that are appropriate when you enter an Indigenous treaty area. So for example,

10:04 what kind of clothing you wear to ensure that everyone is comfortable and you're showing up in your entire enforcement uniform. And all the different kind of tenets around that based on the research that I would then do or had previously done with indigenous groups and working with them hands on to then ensure that we were appropriately reciprocating and understanding their culture. Aside from the one you just mentioned there, could you give us a taster of an example policy?

10:33 Um, what, what, what are we talking about when, when we're discussing new policies? So there's two pieces that I personally worked on. So number one was the actual treaty process. So we have a lot of indigenous groups in Canada and there's multiple steps of a treaty. And based on where somebody is at in that treaty, they will have a certain designation. So for example, if you are at stage two of a treaty process, you are much earlier in the journey. You're still at.

11:03 a very early negotiating stage, whereas if you're at stage seven, you are extremely close to being an autonomous group. And so you are at that finalization stage where you are just kind of putting the pieces in place around your finalized copy of the treaty. It's gone through all the necessary stakeholders in the federal government, any third party stakeholders, the indigenous group itself. And so I would review the policy for any stage within certain GOs across Canada.

11:31 So some were very early stage and I'd be actually outlining the policy. And an example of that is, you know, if someone said, we are going to, we're going to develop this land and build, you know, a couple of factories on it. I would need to flag and highlight that and bring it to another department to ensure that, you know, they don't have any specific feedback points. They can enter the conversation. We would set up calls and meetings accordingly to discuss it and outline it.

12:01 break that down within the policy itself to ensure that it's hitting on both the federal and regional government requirements while also ensuring that it's providing that autonomy to that nation in question. Whereas an example from a stage six treaty would be I would travel to an Indigenous groups territory, maybe I'd fly to northern BC, is terraced for example, and we've set up a call to go through the details of the treaty because it would be

12:30 almost fleshed out. would be super close. And what that looks like, you one conversation we had is they had exactly how many enforcement officers that they would have because they would be self-enforcing their nation as opposed to having federal government. So no police people, for example, they would enforce it. And so looking at, you know, who are they designating for that enforcement branch? For instance, one of the conversations and meetings we had was around someone was about

12:58 probably about 62 years old at age that was assigned to that role. And it was a conversation around, can we bring somebody in to essentially learn from that person so that when they decide to retire, all that learning isn't lost since it's only designated to one person. So what can we do to actually support from an education and a passing along perspective and ensure that it has that continuity beyond that individual's role?

13:24 That was a conversation that I'd fly up to terrorists and we'd break that policy down in half together as a group.

13:31 So, I mean, this sounds like a very big advanced sort of role for you. I'm assuming you would have been, what sort of age was that? Sort of straight after university 21, 22-ish or was it sort of mid-20s? No, was pretty early. It was around there straight after university. So that, yeah, it feels like a very, very big challenging role. What was it that you studied?

14:00 It sounds like a funny jump, but I actually studied criminology and police studies. so the idea, there's a couple of different paths from that. I went into it with the perspective of being interested in law, in the legal field. I came out of it interested in business. So I actually wanted to pivot partway through. Didn't make sense based on where I was. Can just later on an MBA if it's of interest later. So I really enjoyed studying criminology and just learning about it in general. I finished there and decided.

14:28 I got this great opportunity in a special projects unit. So was really excited about that. And I was interested in the federal government from a, again, impact perspective. And yeah, I decided to go into this as one of the routes. I'd say most people coming out of that path will go a couple of different ways. Some will go into policing, some will go into law, some will go into corrections, some will go into federal government. And this was an opportunity to go into the federal government in...

14:52 In a unit that wasn't necessarily tied to criminology, it was a special projects unit, but because I liaised with so many different departments around that, I ended up meeting a lot of them and the enforcement branch actually brought me into that department after for another kind of special projects initiative. And that was building out brand new policy for their officers around indigenous culture. No, I'm always intrigued the degrees that people

15:21 started or where they started from an education point of view and ultimately where they've ended up. This is the first conversation I've had with someone who is sort of criminology, which is really, really interesting. So how long did you do this particular role for? Probably, probably about a year and a half or so. And what would you say in though, in that year and a half were the key sort of learnings that you took away with you?

15:50 I always think of learning as twofold. One is the actual skill sets, the learnings that you develop in terms of the tangible skills and then learnings on the other side being around what career means to you, what success means to you, that inner compass and what kind of learnings you've now essentially recalibrated it towards. I'd say the learnings always reflect that twofold approach.

16:19 So on the tangible skills side, it's a lot more straightforward in terms of policy development, the stakeholder engagement, like I mentioned, running different meetings, conversations, and facilitating them with very differing cultural perspectives was a huge, huge eye-opener for me, especially traveling to these indigenous groups' territories and being welcomed in and understanding different customs. And that was just a huge kind of...

16:49 better understanding for me. So lots of, lots of tangible kind of skills, obviously, you're liaising with a ton of different departments. So understanding that communication path was super key too. But then from the internal compass side, I think it's always the...

17:08 Sometimes the path that you planned isn't the one that you're meant for and understanding what you envisioned may not be what actually is right for you once you're actually in it. And that's why it's so important to do it. So I had this idea in my head that it would be fantastic. And it was, don't get me wrong, I really enjoyed my time there, but ultimately decided to leave because I just found that the pace is a little bit too slow in terms of you'd work on

17:38 on policy and it would just take forever for anything to get done. It was just a very slow paced environment and I wanted something a little bit quicker. I could also see that linear path. So it was outlined for me of, hey, you're excelling, here's the path, what it looks like, your entire career, which is great. it's beautiful and I was super, super grateful, but I was definitely more interested in, if I can see the outcome, I don't want it because...

18:08 I want to be doing really innovative, interesting things where, least at that stage of my career, where the outcome wasn't necessarily known. I was still in a hyper learning phase about what that looked like. think I knew internally what I wanted from an outcome impact perspective, but that can take form in so many different ways. So was more so learning around that. yeah, I think the big takeaway there for anyone listening is...

18:39 listen to your internal compass. Even if you're really enjoying it, even if it's an incredible opportunity, doesn't necessarily mean that it's something that you should stay in. So as long as you listen to that internal compass, and that was a big part of it for me, I had just this magnetism towards tech. was running a lot of tech engagement stuff on the side outside of my policy work and decided to pivot into tech. That's ultimately why I left.

19:07 Yeah, no, there's a couple of bits that I want to touch on. your great, great piece of advice there of following your, I think you call it your internal compass. think I did a degree in design. I got to the end of the degree and I realized that, I don't want to be a designer anymore. That's not what I want to do. So hence the sort of move into marketing. But I think it can sometimes feel as if you are quitting when you change path and it's

19:35 definitely not a case of quitting. It's just actually, I guess, having the courage to change path. So it's the opposite of quitting. It's not backing out and quitting and taking the easy road. It's actually taking the more challenging road and changing the path you're taking, which is often a deviation away from all the money and time that you spent on the education. Of course, there's still things that are relevant. But I guess that at that age, I think even I was thinking, did I just waste?

20:03 20, 30 grand, whatever it was on university if I don't do something in that field, but that's certainly not the case. And then the second one I wanted to touch on is that I think I sort of have this like, it's probably that like Instagram effect of Instagram, you only see the best of people's lives. So you assume that their life is great and they have loads of money and they go on lovely holidays. And I think when I watch programs about law or medicine, I'm intrigued. like, that must be an amazing career. at the...

20:32 the court cases and look at all this sort of stuff and for medicine, look at these surgeries they're doing, this is amazing. But the reality of those careers that you said, it can be very, very slow, it can be very, tedious, it can be very, very frustrating. And I think the slow pace is kind of, reminds me of the civil service in the UK is very, very similar to government or military, the MOD in the UK is very, very structured and...

21:00 You have to do four years in this and then you can get promotion and four years there and then can get promotion and you have to tick these boxes. And it's very, very linear. I think I can, I can definitely relate to the something that is planned out for you. Um, you know, almost like a Ikea manual. Um, that's, it's not exciting. There's not much to get excited about when you know exactly what's coming over the next 30 years of your career. So.

21:27 Um, yeah, some very, very good advice there. So you mentioned that ultimately that's the, why you wanted to leave. the slow pace, uh, too much predictability and you just wanted, uh, a new challenge with a faster pace. that right? Exactly. And a big part of it was tech. was specifically interested in tech. was always interested in tech, but when this opportunity came up, I felt like one I was interested to jump into. I went kind of this route first.

21:54 and ultimately decide to pivot out for those reasons that you listed. That was a great summary in addition to just overall magnetism towards tech. you are sort of roughly 23 at this point.

22:09 probably around there and have to do the math. Yeah, it's early 20s. think we always try and touch on the age because I think it's when people are listening, we've had people in their 30s who have completely changed careers. We've had people who have done it early on. And I think in that still in that early 20s, there's a lot of the urge to experience things, absorb things, try new things, succeed, fail, like learn as much as you can. So what was the role that pulled you away?

22:41 It was less about the role, it more about the space. So super interested overall in the space, was exploring a couple of different opportunities, ended up going into more of an account management role in tech recruiting. And that was an interesting kind of foot in the door. And I was specifically looking for something that had more of an eagle's eye overview across a few, rather than operating in a singular company at first. Just to give me that landscape view, I've always envisioned or always enjoyed that overall ability to have a...

23:09 bit of an equals eye view to a landscape and industry. So that was a really good experience. And just overall, would say overall gave me a lot more visibility into tech. learned, you know, how companies are structured, how teams are built, you know, what companies look for when they're hiring the technical requirements of specific roles and compositions.

23:35 I'd be able to go into companies and work with them on requisitions and better understand how they function, not just from a hiring perspective, but kind of see their overall functionings, embed myself. Sometimes you'd get a desk at certain offices and so forth, and really just see the inner workings of a bunch of different companies. And so that really provided me with an accelerated, comprehensive overview of specific types of companies within the overarching tech umbrella.

24:03 Now, it sounds like this was a very conscious, considered, measured plan of getting into the industry. Was it as well thought out as it sounds? Obviously in retrospect, looking back, that's one thing of I made that decision because of this, but in the moment is, because did you have this exact plan of I think this role is going to get me that overarching view, that's what I need, I'm going to break in, I'm going to do it for a year and then I've

24:33 going to do X, Y, and Z. Was it that planned out? Certainly not to that degree. No, I'd say all of my moves have been extremely intentional, not with the outcome because as you know, Steve Jobs says the dots connect in retrospect, but always with the internal compass intention as opposed to simply taking a role. So it was very intentional in terms of getting in, getting that overarching perspective. Did I plan on, you know, leaving after a year? No, I wanted to, you know,

25:02 probably grow in that whichever company I kind of went to for a while. I wasn't necessarily looking to hop around, but we can jump to that later. Ended up moving and relocating, so decided to leave. overall, I'd say it was a very intentional move, but didn't necessarily know the outcome and the benefit. Maybe had an idea and inclination at the time. I love the, what was the Steve Jobs? was the dots connect in retrospect. Is that the rough quote? Exactly.

25:30 Yeah, I love it. I love that. We should have had that as the slogan for this series. Maybe that's the slogan for season two. don't know. That's great. I've not heard that before and I do like Steve Jobs stuff. But no, think intentionality is another really, really good piece of advice. I think as long as when you make a decision to move, whatever the reason for the move is.

25:57 having intentionality in terms of a move for increasing or developing new skills is an intentionality of moving. So you are in a different industry, intentionality and moving. So you're in a location that's closer to family and that's going to make you happier. know, intentionality is a very, very, a very, very good piece of advice for those thinking about what their next move might be.

26:25 In terms of actually sitting down going, what do I need or want for my next move rather than it just being money? Which it quite often tends to be. Tech, right? So recruiting is challenging at the best of times. My previous partner worked in recruitment and previous company that I worked for, the founder also owned a recruitment company. Very, very challenging industry. Then when you lay a tech on top of that, the volatility of tech, what were some of the things you learned in that?

26:55 yearish, I think you said. Volatility is certainly a part of it. You know, how hiring can differ based on the volatility of the market, how companies adjust accordingly, those were really interesting takeaways to build chat through, you know, how companies were thinking about their hiring process throughout that volatility. Obviously, you know, all the KPIs associated with more of the sales side, so kind of really operating within a company.

27:24 Whereas policy was a very different game and it was a very different skill set, tons of transferable skill sets. But from the actual learning perspective, a lot of it was much more focused on, I again think about those two kind of buckets, on the tangible skills just around overall functioning, operating within a company, viewing how other companies operate, all of those kind of skill sets and just better understanding how they actually function. And what were some of the roles you were hiring for?

27:55 Yeah, a lot of developer roles. So front end developers were pretty common and a lot of quality assurance engineers. So was quite tech focused or quite developer focused, shall I say. Which is a more specialized niche, think, within recruitment, certainly, isn't it? Yeah, it's a little bit more specialized, less go to market roles, much more technical skill set.

28:24 better understanding what the difference between developer who can code in Python is versus any other language and really breaking those down more granularly.

28:36 Okay, so you touched on your reason for moving or moving elsewhere and looking for a new role. So do want to just explain how that came about? Yeah, definitely. It was a little bit unexpected and was just such a blessing and incredible opportunity. But my partner at the time was moving to Europe. So he was going for work in kind of the sports area.

29:06 And it was a good opportunity if I wanted to go with him. Otherwise we would do long distance. It was kind of up to me for what made sense. And I wasn't at a point where I wanted to necessarily kind of shift my career entirely. was fairly, you know, just interested in super courage driven and curious with what I was kind of building towards. So I didn't want to necessarily kind of rip it out, move somewhere for an undetermined amount of time. But I did decide ultimately that it was an experience that we'd probably, we'd probably

29:34 you know, regret not experiencing. And so I figured I would try it and ultimately was ready for a shift from that role in general. Cause again, the two pronged approach learning, the chandler skills we talked about the internal compass learnings was, know, absolutely. I love the tech industry recruiting isn't, you know, the path for me long-term. Um, just from a overall kind of work style, there's a lot of repetition too.

30:03 It's very relationship based, which was great, but I was really interested in more of the kind technical learnings that perhaps weren't offered within that scope of role. And so I was ready for a shift overall, but not ready to completely uproot. So I decided to go for four-ish months overall. So I ended up leaving that role to go to Europe and join him for a few months. So he was there for just shy of a year. And then I joined for...

30:31 three months with him, did a traveling month alone and just had the most incredible time. It was such a wonderful experience and it was also a great experience just to be immersed in a different culture, different language. We lived in a village where nobody spoke English, so I picked up Italian and just developed these different skill sets and I was learning at the time through a role and had a wonderful time and came back to Canada and said,

30:59 Okay, I'm ready. I'm ready to move to Europe, but I'm also not ready to sacrifice what I'm interested in. I will find something that's a middle ground. And so I was specifically looking for something remotely after that. Okay. So where was it you traveled in those three and four modes? Give us the highlights of the places that you visited. Yeah. Well, we actually lived in Italy, which is where you just came back from. Very jealous, I'm sure, of all the beautiful pasta that you got to consume.

31:30 We lived in the North and Trentino Alto Adige is the province. just about two hours south of Austria, right in between Venice and Milan. It was a really, really beautiful experience. It's a much more small town. It was in proximity to airports, in proximity to larger cities, but because of that smaller town experience, it was one that was much more immersive, which was really cool. I joined a local soccer team, would travel around.

31:59 I didn't speak any Italian when I first arrived, left being able to communicate. Nobody else spoke English. So was a really cool, again, educational experience just from a different lens, much more immersed. And what were you doing for the three and four, was it three or four months just living or was it three or four months in, were you working sort of nine to five during the week or was it just a case of immersing yourself in the culture without?

32:28 without having to work? Without having to work. So I actually left my role and decided to go for a few months and then would either come back to Canada or move wherever I decided to move for a role itself. Or if I enjoyed kind of the European lifestyle together, then would move to Europe and do a role there. So it was much more of a transitional period where I wanted to just fully immerse myself. I would spend hours a day studying Italian out of a textbook, you know, gained a lot of...

32:57 I'd say more cultural insights, got to travel around, spent, you know, a good month on the road between different countries, Ireland, England, know, Malta, traveling around as much as possible within the kind of timeframe that we had. He was working at the time, so we were kind of constrained on the time together for traveling, but we definitely made the most of it whenever we'd have, you know, a two day period or anything of the sort. you mentioned a couple of places there. What was your

33:26 favorite place you visited? I think I've got a little bit of bias towards Italy because we spent the most time there and I always feel like the more time you spend somewhere the more greatly you appreciate it because you get to see these depths of a place that otherwise you don't get when you're visiting and so because it was you know just such an immersive experience it would hands down be northern Italy. There's so much so much beauty to it the people are incredible the food is amazing.

33:57 And it was just a wonderful experience. find myself in the most, I'd say, most humorous experiences now in retrospect, but learning to drive standard, driving hours through vineyards to new places, to go play soccer, or do some work over here and there. And it was just a really kind of pivotal experience, I would say, overall for both of us.

34:23 Yeah, I've got a couple of friends who are traveling northern Italy and then Austria at the minute. So I'm watching their stories every evening and it does look stunning. Them sitting on or sitting in vineyards whilst I'm back working is tough to handle, but it looks lovely. So after you spent four months there, you came back to Vancouver and decided that you wanted to make more of a permanent move across the Europe. Is that right? That's correct. Yeah.

34:51 And what was the next step from a career point of view then to facilitate that or make or to align with that goal to move? Yeah, good question. I was specifically looking at the intersection of marketing and tech and software. And so I was looking for a role in that realm, whether it be on the ground. you know, it was a bit tough based on our kind of proximity of where we'd probably live in Europe to have something on the ground. I mean, it could. So I was looking at European roles.

35:20 And then I was looking at North American remote rules, just trying to see what type of intersection I could find there. This is obviously like pre-COVID days and so forth. frankly, it was really tough at the time to actually like find any jobs that were remote from North America at that intersection. And so I was just kind of keeping an eye out and pretty immediately actually found like the perfect role, was super excited about it. so...

35:48 ended up interviewing and taking that role, which was in the marketing and tech space at a company called spiralize working in the commercial optimization space. So pretty data-driven, quant marketing, full funnel optimization with SAS companies. And what was the, what was the role title? A head of growth.

36:12 So you managed to find a company that allowed you to work remote, which was this head of growth role. So did you move back across to Europe pretty quickly after that or how did that work? Yeah, good question. Because it was, you know, that time where it was a little bit trickier to hire or get hired globally remotely. So I worked in North America for probably six months or so, maybe a little bit longer.

36:41 And in that time I was traveling around a lot. so I'd go meet with the team and so forth. And we'd talk about geo. And it was the kind of experience again, where yes, I wanted to move to Europe. was something that I specifically kind of asked about, but I was also flexible. I didn't need to go right away. If we needed to build something out, boots on the ground, totally fine. I was committed to building that vision together. But I knew it had flexibility and that was a big part of it. So I did that boots on the ground and building.

37:09 travel around Seattle to San Francisco for a while and then it got to a kind of an inflection point where we had a conversation around Europe and thankfully they were like absolutely moved to Europe that's actually great from an expansion perspective and obviously you could take a flight back if needed for any kind of events and so forth as they're a little bit more ad hoc right now so ended up kind of getting their blessing which I was super grateful. And what was it that attracted you to a more

37:39 marketing focus role? Because I think based on your first couple of roles, specifically the last role, obviously, account management, of a, I guess, recruitment is very, very similar to sales in a lot of ways in terms of the daily structure that you're selling a person's skill sets or you're a business to a person to try and head on them. But what was it that drew you to more of a marketing focused role?

38:09 from your background? Yeah, definitely the education component. think that is ultimately what marketing does. It shapes perception and can educate accordingly. So shaping perception is a way of providing information, which then in turn shapes that perception, which can be in the form of education. And I'm very passionate about education, so I've always been drawn towards marketing. I think, you you jump.

38:36 from role to role, but there's a lot of, I'm sure everyone has threads in between those roles. Background things, for example, I was working with a nonprofit that I ended up working with for over 10 years in the education space. And then I took marketing courses on the side. So all of these kind of components or ingredients, if you will, were coming together to create this kind of recipe at the time. I was also working with local

39:04 tech organizations and kind of group meetups and having coffee chats with people and so forth. So all these kind of, again, ingredients came together to create that recipe and understanding of marketing is a different form of education. But again, it's more of that internal compass. I don't necessarily know the outcome, but I know that's the path and just allowing yourself to follow that intuition. Interesting. Yeah, it's an interesting

39:34 move from public policy to tech recruitment, at least to get into tech and then again, to make that decision, like you said, based on the internal compass of education and marketing being a way in which you can do that. you looking at your notes, you went from head of growth to VP of optimization. How long, how long a period of time was that? Probably about a year and a half. So pretty expedited. And that was because we had a key

40:03 executive team member that exited the company and kind of left us with this internal gap. And, you know, I assumed that we would probably hire for it, especially somebody out of our office, which was in the US. But it ended up being at the time, you know, when I would help support that person with the transition and fill that gap. And that was completely okay. And, you know, I didn't know which direction it would go, especially because I was located in Europe at the time. And then it ended up being that, um, it was the kind of thing that I could kind of step into and help support with those.

40:33 areas and we ended up building together for over four and a half, close to five years in the end.

40:41 Four and a half, five years, is a very good stint in terms of, I think we've touched on it in quite a few episodes where a year is one cycle of that role and to understand a role, to do the role properly, think two full years in a role is kind of like the minimum. You've done it the first time, you learned the basics and then the second time you optimize, you iterate on that first year and you look to solidify these things that you learn. Only then...

41:11 Can you fully understand the role because you've done it twice over? Um, and I think four or five years is a, uh, quite rare in terms of people sticking out four or five years in a role. think especially trying to sort of figure out your rough age at that age as well. Four or five years is a good amount of time in one company. was it a case of you were challenged, you were learning, you were developing, and basically a lot of the boxes were ticked during that period of time and there was no reason.

41:41 to even think about leaving? Absolutely. Yeah, extremely challenged, never a dull moment. And I would say I was fairly entrepreneurial in nature. So it was the kind of situation where I had the autonomy to actually build and create and help, again, build something from more of the ground up. And so for me, was, I mean, I was super excited to A, be building with the people I was building with, and then be building what we were building.

42:09 And so there was never a moment within that journey that I wanted to hop ship or anything of the sort. I think you nailed it perfectly around repetition, two years being a minimum of seeing the iteration cycle. And you also see market shift because that is a big component too. So you've got the internal shift and then you've got the external shift of an organization. And they can happen at different times, but those multiple cycles really help you go through those processes and understand them.

42:38 And so there was never a point where I felt like, you know, in a four year stint, for example, that it was too repetitive. We were always doing something novel, always kind of building. And so I felt like there was a constant growth development. And frankly, I was just really excited to build, to build what we were doing. wasn't, you know, looking for a role to, to fill kind of that skill set for me. was like, I'll find that skill set. I'll build that skill set myself here.

43:07 Yeah, we're very, fortunate in technology or SaaS that things change, develop very, very quickly in terms of, according to those external shifts to industry trends, market changes, COVID, like all of these external things. The industry we're in changes very, very quickly, which is if you have that, I guess, need to continuously learn, continuously be challenged.

43:37 Otherwise you have that. I think you said you were fulfilled in that you didn't have this like missing thing that you were looking for. So you weren't even tempted to look elsewhere because you were professionally sort of fulfilled. So we are lucky in technology that we get that constant challenge. You learn something and three months after learning it, it's old hat. You have to learn something new. that's.

44:01 That's a very, very good thing about the industry. If anyone's thinking about getting into technology or SaaS, definitely do it because it is, I think we've called it like an incubator for learning, which is what one of the biggest draws about the industry. So four or five years, like we said, long time. So this is a fairly big broad question. What were some of the key learnings what did you learn in that four or five years going from head of growth to VP of optimization?

44:30 Yeah, mean, a ton. The long and short is I learned a ton. Everything from, you we built an internal product, so everything from the product build perspective, you know, all of the different layers around that through to, again, seeing the, we kind of had a bifurcated system where we had the product and then we also had a service. So I got to kind of learn both sides and it was the absolute kind of perfect blend between the two because I got the more kind of internal operating from the

44:59 singular product perspective, but then we also worked with a lot of software companies to help provide that software and then service that software. And so it was everything from, I mean, the actual implementation and optimization of SaaS Funnels. So think everything from top of funnel all the way through to NRR. And every company measures differently and we'd work with every company differently. But the entire process of

45:26 How do you actually measure this quantitatively? How do you think about the creative? How do you think about failure too? Like it is really a data point. So leveraging that truly as a data point to then inform the path forward from everything from like a marketing campaign all the way through to a go-to-market strategy. We can test messaging within that full funnel optimization process, see how it resonated. So it's kind of like the nascent stages and now we've got a ton of different resources.

45:55 for message testing and optimization. So some of them were very quantum nature where we wanted to optimize based on pipeline and revenue objectives. Some of them were very strategic in terms of we want to measure certain messaging campaigns. want to message, just measure overall, know, sales messaging and so forth. So there was different objectives, but everything was a very quantitative measurement and experiment at some point in the funnel of a SaaS company's journey.

46:24 So got a lot of exposure from that side. Which sitting in a marketing team, SaaS marketing team, I can tell you is very, challenging optimizing the funnel in a good way, as in challenging and an enjoyable challenge to try and optimize the funnel. So were you an agency?

46:53 optimizing funnels for other companies. Exactly. Yeah. We love the service. We had a product that we built used as a bit of a wedge and then we'd leverage the two from a service perspective. Interesting. Okay. So an agency is a whole different bag to in-house like very, I guess when you, when you're in-house, you're looking at one funnel for three, four, five years, however long you're there. You must've seen

47:22 tens of funnels, hundreds, I don't know how many it would have been over four or five years. Are there any nuggets of advice you could give marketers listening in terms of trends or patterns you saw in the funnels that you worked on? Yeah, I mean, was such an interesting time. was at the point of marketing where people weren't familiar with the concept of commercial optimization. So was a very educational journey initially.

47:50 And then you could see it take kind of take traction and people understand that more efficiency metric to pipeline generation, revenue generation. But the most sophisticated teams would measure to revenue or NRR. That was super rare at the time. know, as you know, most companies were measuring MQL at the time and then progressively would go to pipeline and revenue. So I do think we're at this still like.

48:16 second stage of what that looks like. Ultimately, think marketing teams will be tied entirely to NRR. Everyone will be aligned around that. Everything's a proxy to get there. But the nugget that I can say from looking at, mean, hundreds of different software funnels was really alignment and the importance of measuring down funnel because I could see everything from organizational shifts based on companies that measured further up the funnel comparatively to companies that...

48:45 would measure further down at more of the revenue or NRR stage. So that alignment would really kind of shift the way that they go to market and the momentum that they had. And when you say alignment, do you mean alignment between marketing and sales, for example? Exactly. The entire go-to-market organization, because it was a kind of initiative because it touched on so many things. It wasn't just a marketing initiative. So we would work with the entire executive team. We'd have CEOs of companies.

49:14 in the conversation. was a very strategic initiative for them. So we got to actually work with the entire go-to-market executive team most of the time on these kind of campaigns, initiatives, tests, experiments. And that was a big kind of takeaway of, okay, the companies that measure further up the funnel have less alignment of their internal team. This sounds obvious to us now. At the time was a little bit less obvious, but have less alignment. And you could see it, know, some companies we worked with for years. So I kind of got to see funnels.

49:44 as they shifted over years, their analytics, their funnels in entirety, and also their teams and their revenue and momentum and how that would shift. And the companies that were more greatly aligned having marketing focused further down the funnel were certainly more performant across all. Yeah. No, I think I'm very, very fortunate to work at a company like Dalefront who believe in this one revenue function, the marketing, our driving pipeline for sales.

50:14 Sales are closing pipeline for marketing, vice versa. We like to explain their MQLs, SQLs, closed one all the way down to ICP fit. We call them hitch segments internally, which is essentially like a red amber green measurement of the quality of an account that you're bringing in. So optimizing more towards the, we call it blue internally just because of the brand, but blue is like our top tier of customer.

50:41 So we are trying to increase the proportion of our customer base that is blue and bring in therefore more blue leads and more blue throughout the funnel, cetera, et cetera, et cetera. So we're very, very fortunate or I'm very, very fortunate to work in a company that is aligned and does believe in that. But it is still to your point, quite rare. And there are still quite a few companies and industries who are stuck on that MQL hamster wheel as they call it. I think it's probably the most well-known phrase.

51:11 Um, but I think during this, again, I'm roughly mapping out when this would have been in it, you know, Chris Walker talking about demand, Jen, and, um, from a refined labs point of view, he spoke heavily about optimizing towards, um, the, you know, optimizing your funnel and, uh, aiming to increase the number of opportunities in pipeline that converted at a certain amount and then quality and things.

51:41 Exactly. there's still a long way to go. Yeah. I remember when he started talking about it and it was just so great to have an advocate in the space talking about the actual efficiency of funnels. so that, I mean, that was a key learning just overall, I'd say how companies measure and how that is reflective across their overall alignment and then accordingly company growth. A couple others would be around

52:12 I'll pause here for a second.

52:19 I think a really interesting learning. And again, these might sound a little bit more obvious here in 2025, but is the power of velocity in terms of experimentation. So it was again, a time where companies were still dabbling in experimentation. They were just kind of coming around to it. They were just kind of understanding how did that process even work? What's the benefit of it? So again, it was super educational, but the power of

52:47 leveraging experiments for data. And that's it. Experience failure, not worrying about it, it's all a data point. So companies that are very, I mean, open minded to experimentation were certainly the ones having the most progress. And that was very obvious. And then also how you actually get to a hypothesis. So the process of experimentation in terms of what that actually looks like to get to the point where you run an experiment.

53:17 was a really interesting learning. And I would say the takeaway for everyone listening is less experimentation by committee at the final stages. So think of it like a funnel in itself, where you are essentially crowdsourcing ideation from as many people as possible that make sense and then funneling that in. So ultimately when you are nearing in on an experiment,

53:42 and running and managing that experimentation process, it's a lot more narrow. So narrow group. then again, you want to elongate the funnel on the outside. So think of it like a hourglass. You want to bring in a lot of ideas. You want to refine them in a small, small group. And then you want to disseminate the learnings to everyone again, because again, like I mentioned, had CEOs joining. It was a very novel concept for a lot of companies at the time. So we had a lot of experimentation by committee come in.

54:12 And I'll say, you know, there's never so many opinions about experiments and what should be done. And the most important thing is just creating that hypothesis and actually running the experiment, learning from it and ensuring that that learning is actually baked into all kind of future experiments and learning. And that speed is what creates the feedback loop. So less experiment by committee. Yeah, it's a very, very good piece of advice.

54:37 I think experimentation naturally is a very, very subjective opinionated or a very, very subjective process, which can be led by strong opinions in terms of, I don't like that text or I would prefer this, which is the, obviously the hypothesis, but yeah, I would definitely agree with the reducing the size of the committee or getting fewer people involved when it gets to that infraction point or.

55:06 the middle of the funnel, whatever you want to call it in terms of running the test is it's very, apt. actually finished a test yesterday on our homepage, which was, I think it was 23 % more leads with the new homepage design, which was obviously a great result. Like 23 % is it's not always that you get such a sway, positive sway in terms of the results. But yeah, to have that, I think you called it,

55:37 What was it? The word began with V. word is literally jumped. Velocity. I was thinking volatility. like, no, that's not velocity yet. We have touched on that already. Yeah, yeah. like pipeline velocity, optimization velocity. But yeah, I actually find it one of the most enjoyable parts of marketing because I like being proven wrong because I feel like I learned so much more from being proven wrong.

56:07 And when you run A-B tests quite often, you go into it thinking your hypothesis will be correct. And if you end up learning that it's wrong, that's just as valuable as it being correct because you've learned how not to do something or you've learned why something might not have resonated in the way you thought it would. So I think whatever the results, whether it's positive or negative in terms of a win or a loss on those tests, you learn something. The same goes for career, right?

56:36 It really is the insights that you generate from every career experience that I'm sure you surface and do an incredible job at surfacing the insights from every jump and every kind of experiment, if you will, or data point. Yeah. And if we look at your, um, your career up to the point that we've got to now in this discussion, you've taken nuggets from each of them and you've basically tried to combine them and double down on those, take that forward and then bring something new in and you've

57:05 essentially optimized your role in your career over a course of 10 years to reach a point where it's a role that best suits that gut feeling that you spoke about that sort of in a compass. So you did this for four or five years. It sounds like it was a very, very good time for you in terms of development, growth, learning. Am I right in saying that after that four or five years, were like, right, marketing is where I want to be. This is the sort of function that I want to be in.

57:35 And it was just a case of then, right, what's the next step for me in this function in terms of the challenge of the learning? A little bit. A little bit. And I kind of go back to think of them like parallel tracks. You you've got your jobs that everyone sees on LinkedIn, and then you've got your parallel track that is your almost personal experimentation. And that doesn't have to be career oriented. It can, it cannot, but it's just.

58:00 following curiosities and doing different things on the side. Like I mentioned, being involved with educational nonprofits on the board there, being involved in tech kind of meetups here locally and so forth, taking marketing courses online. Like all the things you don't necessarily see on this parallel track was a huge guiding function for the actual career track. So at the end of my tenure at the company,

58:29 I'd say kind of realized I've got, again, similar to the criminology. I love this. I love learning. I love building and supporting companies and building our product and also leading in a remote environment. That was a big part of it too. We scaled our organization, led in an entire global remote environment, owned revenue for our company. so I was just having a blast, really enjoying that kind of run, but was noticing that my heart was still in startups.

59:00 So a lot of companies that had the sophistication at that stage of the journey for this type of experimentation were mid-market enterprise companies. And, you know, think of the type forms, the Sophos, the Oracles of the world, you know, a lot of CRM companies we'd work with. But my heart was always in startups. And so I'd have a lot of startups come to me.

59:24 and ask for support. And so I'd end up consulting or just supporting them on the side in various capacities, but it was only scalable to a certain degree, obviously. Time is finite. And so I'd create resources to be able to help startups at a little bit greater scale, but it still wasn't the kind of support that they needed. They needed something a little bit more hands-on. So I was always just really passionate about earlier stage companies, but didn't have the ability or it didn't make sense for our go-to-market to actually build out an SMB function.

59:55 at the time. And so I was also, again, very just embedded in experimentation of my own degree on that parallel track. So I was interested in different ideas. I was experimenting. I was learning to code by myself. was running all these kind of parallel ideas. And so I ended up joining an incubator for an idea I had, not because I necessarily wanted to build it out, but more so just out of interest for what that actual process of building a company is from.

01:00:24 start to end, granted knowing that it was through a program and not realistic of all circumstances. I was more interested from, guess, that academic side, if you will, of like, what does that look like? I want to kind of get my hands dirty with this. So I went through that process on the side and realized in that process that I was really passionate about helping other people with their ideas. And I was really interested in my idea, but I didn't feel like it was a sharp enough

01:00:53 pain point for me to go all in on solving and I didn't feel like I was the unique person to solve it frankly. And there was also some kind of solutions in the space and now our solutions in the space. And so wasn't as like acutely keen on my own idea, but I was running our cohort group through this program and I just had such a great time helping other people with their ideas. And so that was kind of a data point.

01:01:23 along that parallel track that eventually led me to have conversations with my network, to expose the venture lens, to understand more about the venture space. And that is how she would create my interest in venture. So when I did move into venture eventually, it was a very intentional move. was specifically looking to move into venture at the intersection of marketing and community ideally.

01:01:51 But it's, it's, I would say not a lot of venture firms have this kind of structure that GTM fund has. It is quite unique. And so I was just more so keeping an eye out, having conversations with my network. You know, there were a couple really interesting, innovative companies, but again, I didn't feel like they had that intersection and was just kind of keeping an eye out. And, uh, that's kind of how the move into venture was, was, uh, sound like a very curious person.

01:02:19 Yes, would say definitely a curious person. I, Stephen Bartlett talks about curiosity being super power. And I think when I, um, when I've hired, uh, for my team, curiosity is one of the things I look for most because I think people who, uh, want to know how something works or will go out of their way to learn to code or whatever, just because they're interested in it or want to join cohorts to try and absorb and learn more. think curiosity.

01:02:48 I certainly agree with Stephen Barlet. It's a superpower because you can level up for far more quickly and you think it's it almost frustrates me when people are content with just the way things are rather than understanding how they could be or why they work the way they work or if there's a better way of doing something or something like that. So curiosity. It sounds like throughout your career, you've been very, very curious about the internal compass, I guess. Is it a case of

01:03:17 You feel this pull, this internal compass saying that could be interesting. And then the curiosity is like, I've got to try it. Do you get that like itch of having to scratch the itch? I think it's almost the reverse. And first, I love Darius CEO, big fan of everything Stephen Bartlett is doing and the space and also the media platform that he's built out. He's at a really interesting intersection of media and investment now too. But

01:03:45 Overall, I'd say the curiosity is actually the first part. So curiosity is what informs and kind of creates that data and personal feedback loop that then informs a jump. So it's less of, I've got to try this and scratch that itch. It's more of almost a, you know, you know, because you've done all this personal feedback loop experimentation, again, not intentionally purely out of curiosity. That way, when things occur, there's a lot more clarity.

01:04:13 You're lot more almost vulnerable with yourself in terms of having that career clarity or understanding of what you're interested in building, who you're interested in building with. And I think that's a big learning for myself, for people, anyone listening is often we place a lot of emphasis on external validation, external factors of what a career should look like and what that means. Typically it's title, typically it's salary. Those are the two most common. But really,

01:04:43 You know, that is externally created. So being okay with finding that internal compass. Again, I keep repeating that, but it's the best terminology I have for it because it really is like, how do you kind of take away, and it's okay to have those external factors. We all have them to a degree, right? So how do you actually leverage them almost as fuel to better understand your own path and have less external pressure?

01:05:09 from an attainment perspective to have these kind of validation points and just pursue what you genuinely find fulfilling and kind of find that Venn diagram with yourself around, you know, what is fulfilling? What does the world need? What can you get paid for? Yeah, very, very, very interesting. it's, I love that the, you talk about those like internal data points or those data points. And it's almost as if you've applied a conversion optimization theory to

01:05:38 uh, your, your career or the self-awareness of these single nuggets of data of I really enjoyed that. Or I found that super, super interesting. That was the most challenging but rewarding year of my life or career. And you've got these data points to your point and you've learned from those data points and you, as you would in marketing, you invest into the areas that are going to give you the best ROI, the ROI in this situation being happiness development.

01:06:08 rear growth, you know, that I really like the data points. I don't think many people would look at career from the point of view of, you know, 10 or 15 years and continuously optimizing towards your perfect role using data points. That almost is like a very, very logical, technical way of looking at it, which I love. It's like for my like slightly autistic brain, that is I'm loving that in terms of

01:06:37 finding those data points and optimizing towards the data points. So I love that. And then the second one is it sounds like a very, very stoic way of looking at a career in terms of those external factors, the job title, the salary being things not necessarily in your control. And the stoics talk about focusing on the things that are in your control in terms of how you perceive things, how you can react to things.

01:07:06 focusing on things that are in your control. So I love those two things, the stoic view of looking at the career and also the data point. I absolutely love that, the two very, very, very good pieces of advice. So explain to us the role, like the venture side of things. It might be slightly confusing for those who don't know much about venture and to your point about that role in particular, not being very common in that area.

01:07:34 So explain to us what the role was or the industry, the field is. Yeah, you bet. That's a great point. there's, I'll kind of break it down overall is essentially GTM Fund, we are a venture firm. So we invest and everyone invests at different stages, but we invest from pre-seed to series A. So what that means for us is we're writing kind of checks that are in size about 500K to 2 million.

01:08:01 into singular companies. These are all B2B SaaS companies, runs the gamut in terms of verticals. We've got specific focus areas, but we do invest in everything from vertical to infrastructure to AI-native to RevTech. So we've got a really, really interesting, impactful portfolio built out. Just to break it down very simply, we have investors externally that provide capital for us to then invest in B2B software companies.

01:08:31 And what that looks like, we've got a bit of a unique composition from a venture perspective is we do have institutional investors, but we also have go-to-market operators. So these are people that have been in the trenches, they've built software companies, think CMOs, CROs, know, CCOs, chief customer officers. And so these are all individuals that, you know, have the expertise directly. when portfolio companies, companies that we invest in say, you know, I want to build out a sales development playbook.

01:09:00 we can actually connect them with Lars Nilsson who built it out for Snowflake. And so they have that direct support built in. And then in turn, it provides a lot of diversification for operators beyond their singular kind of operating company that they're at. So they actually get upside and exposure to all the different companies out of that fund that we're investing in. And in turn, get a lot of kind of career acceleration from a network perspective and from a media perspective, as we do also have a media company on top of it.

01:09:30 I'll pause there. Happy to go into any areas. Are you marketing the, you're marketing to prospective companies that are looking for venture backing? So is that, would that be your ICP? So we have, yeah, from an ICP perspective, it's quite unique again, just because we do have the media background. So our general partner, Max Altshuler back in the days.

01:09:57 eighth employee at Udemy. wrote a couple of bestselling books on hack and growth, planned the first couple of saster opens with Jason Lemkin and built a pretty heavy network from that. Ended up building out a media company called Sales Hacker, grew to about 175,000 members globally and then in 2018 sold it to Outreach. So he had this media background and understanding of the impact of media. So eventually when he built GTM fund, we always infused media throughout.

01:10:25 So we've always had a media brand. then just in 2023, which is when I joined GTM fund and why I joined is because we reacquired very full circle moment, reacquired that same company from outreach that he once founded. So we rolled sales hacker up under our media brand. It's called GTM now. And that essentially 10 extra distribution overnight and just helped us expand the media company into more of a media platform.

01:10:53 So from that lens, a lot of the marketing looks different than a traditional venture firm. Traditional firm is a lot more heavy in terms of events, of traditional marketing and PR, whereas our emphasis is more greatly on media. then marketing is almost gets the benefit of the media. It's kind of baked into that. There are some more traditional aspects. So for example, when we announced our Fund 2 in February,

01:11:18 There was a traditional kind of PR campaign around that. So I ran that traditional PR campaign, but predominantly my focus areas across marketing rolls up to more of the media platform that we have called GTM now. I find this, I'm fully bought into it. I find this very, very interesting. You the, you know, you're joining us for an episode of something that sits on the stream, uh, like a B2B streaming platform. So we're very much on the same page. Talk, explain to me in really simple terms, the type of content and for those listening, the type of content.

01:11:49 that they could consume on GTM Now. Yeah. I mean, I feel like that's exactly what you built, Jamie, is a platform that educates your buyers and supports and provides that as a resource. I think you're also doing a very similar thing, And similar boats, but GTM Now is specific to B2B SaaS. So it's a resource and platform across kind of career and overall company growth. So if you're looking to grow your company,

01:12:18 understand what's happening in go-to-market, how companies are actually growing. Think of it almost like how I built this in a way, but from the go-to-market side. What were you actually doing from the motions around it? What are the tried and true practices that went into company growth? How did you shift your emotions from PLG to SLG? What's the behind the scenes? And part of that was we've got this incredible network. are an operator-led fund, so we have a community of about 350 operators.

01:12:46 And these conversations occur behind closed doors. So we said, how can we help scale a lot of these conversations or scale the conversations that you're having with our founders so that other people can get the benefit from it too, that aren't within GTM fund necessarily. And so that's really the mission of GTM now is expanding that knowledge from some of the best operators in SaaS. And sometimes we share our perspectives, you know, being a VC, investing in a lot of companies around what we see too, but it really is how can people.

01:13:15 advance their company or grow their companies and advance their careers. Yeah. I'm looking at it in the background now. That's why my eyes are on another screen. I absolutely love all this sort of stuff in terms of the education, the community, building out something that first and foremost provides value rather than seeks something from your audience. So what made you, I guess, seek that?

01:13:46 Because it is, you know, within the broader like marketing and then content marketing or brand marketing, it is a very, very specific sort of a niche to go into what, what I know you spoke about education previously in your career, but what was it that drew you to specifically like the content community sort of Great question.

01:14:11 Maybe before I jump into that, actually, you made such a good point around the value part, giving value first. And I think that's a common theme that I actually see across all of the different puzzle pieces that have made GTM funded GTM now. So for example, you know, going from having these meetups in the Bay Area, like Max or GP, it's like, how do I scale this? How do I actually help more people? I'll create a media company. And then the same thing when he had, you know, a lot of early incredible angel.

01:14:40 investments into companies at a very early stage, a lot of operators in his network would come to him and say, no, how are you doing this? How can you help me do this? And that was kind of the idea and ideation that he backpocketed, backpocketed, pardon me, around GTM fund so that later he could pull it out and be like, how can I help other people expand this? And then the same thing with GTM now, it's okay, we're having all these conversations in our closed community and with our founders, how can we actually expand that to other people? So that's really kind of the mission, I would say that.

01:15:10 underlies GTM fun, if I actually look at the historical inflection points, but it's just an interesting takeaway based on what you said. But yeah, I think you asked a really good question around education overall and kind of how that feeds in, how this kind of role in particular feeds in. And I think about it terms of triangulation, you know, there's been a lot of different types of roles and threads throughout these tracks of life so far.

01:15:37 and career so far, but they always have the same kind of triangulation around innovation. And so what that takes the form of is technology, oftentimes education, often taking the form of marketing, and then community. And so those areas are always have always been constant from every area that I've done, whether it's, you know, on the traditional career track, or whether it's through this parallel track of, you know, things I'm doing outside of my, my

01:16:04 my job, if you will, or my role that people would see from the external. So those are the areas of triangulation. feel like this role is actually the perfect encompassing of all of those. So traditionally, I would get those inflection points from different areas, but this is actually all encompassing of that triangulation. the innovation, the technology, we're supporting, directly supporting innovation through investing in founders, supporting them with their go-to-market.

01:16:32 That is what we come in at the earliest stages to help them build out because the thesis is technology modes are declining. Go-to-market is really that wedge and differentiator. So we get to support, and it's such an honor to be able to do so, that innovation at such an early stage. The education piece is probably one I didn't actually anticipate. I didn't anticipate education coming in the form of media. I think I traditionally just always knew it in that more traditional educational sense.

01:17:01 And that's how I was involved with organizations to date that would support in that more traditional way, especially at early stages of educational development for children. But media is education. Like we right now get to help, again, like I mentioned earlier in our conversation, shape perception, shape understanding, and that is education. And so it's a huge honor to be able to actually work with operators, work with founders, work with our team to be able to share these insights at scale and educate.

01:17:31 the greater kind B2B SaaS ecosystem on tried and true go-to-market practices. And then the third component, the community side, that's always kind of been a constant in terms of I've always organized, you know, local meetups, been involved in, like I mentioned, sub tech meetups and so forth. So I've always had this community component on the side. And now we actually have a formal community that, you know, we get to run events for both digitally, offline, in person.

01:17:59 and support with their careers and overall networks. Yeah, I think that's a very, very, well, a perfect answer to the question of what drew you to it that you said it's that Venn diagram finding that point in the middle that combines those three data points that you've called them, data points of, I really enjoy these three things. They've been threads throughout your career.

01:18:24 quite clearly. And then this has just been the perfect role to combine those three threads into one role, which is very, very similar reasons for why I absolutely love content and why I wanted to double down on content in this particular role and plan to do so for the next few years at least. Very cool. I love what you're building there at the career ladder. I've listened to a lot of different episodes and it's really insightful to see people's experiences because it's the kind of insight you don't get and that's the whole purpose, right?

01:18:52 You don't get just looking at a profile, looking at a CV or anything. So it's been really helpful to hear people's journeys. Well, I appreciate you saying that. I think it's exactly why we created this series. Because I think fundamentally people are quite nosy, but nosy in a good way. they see someone in a role that they would aspire to be in, but they don't necessarily have the resources or the knowledge of how they get there or what is needed to get there, what they need to learn, what they need to.

01:19:19 Um, what skills they need to add to their repertoire. I think hopefully in, in providing, um, these sort of deep dive conversations of people's careers from A to B, um, that hopefully it will give people some nuggets of, uh, of insights, you know, these data points that we keep talking about the internal compass, those little nuggets of advice and the insights, I think they are super, super useful. So I mean, and, GTN now I'm gonna, uh, after this, I'm going to go and have a look at it and, um, check it out. Cause I think.

01:19:49 anyone who's doing something similar in terms of the value piece, the education piece. I love to see how other people have done it, how they've built the communities, mainly so I can learn and steal things, but I will definitely be going to check it out. just very, very quickly, do you have a hard stop in five minutes?

01:20:15 Don't no, we're Cool. I'm good to run away. Yeah, I can do an extra 15 minutes. So for Tom editing this job, so you just cut that out, please tell Okay, so in terms of we'll do the question so how long have you been in role currently Around a year and a half

01:20:41 So you're, like we said, you're midway through that second cycle. You've done it once, you've learned all the processes who you speak to for this, who you speak to for that, the people you can rely on, the designers, the videographers, all of that sort of stuff. So you're in your second cycle of things, which I think, like we said, I think it's the year that people can make most impact and they sort of come out of themselves because they've sort of proven to themselves.

01:21:09 of imposter syndrome right I can do this role I'm still here after a year the second year is when you get a bit more confident uh you're not as worried about breaking something or failing so what are you learning or what have you learned um in the last sort of six months let's have a look at like the last six months of you're now your second cycle what are some of the key learnings

01:21:32 I mean, that tangible side is really, I mean, the venture space. the ecosystem, that's been a huge learning in terms of just overall industry functioning. think we are accustomed to the, you know, calendar year cycles, but I almost think that a little bit differently in venture in terms of they're usually a fun cycle. So when I think about, yes, I'm in year two, I'm actually in, I'm going to be entering year two of, for example, our fundraising process.

01:21:58 I'm in year two of our media company. each kind of area almost has their own cycle. And so with that is almost like a longer term impact and effect where we will finish a subsequent fund fundraise and then deploy that capital far longer than the typical calendar year. And so it's really running through that process multiple times. It gives us the repetition.

01:22:25 From that standpoint, from the actual fund side and operational side, from the media company, that's closer to calendar year. I almost think of it as, yeah, truly calendar year, because it was January of 2024 that we really kind of relaunched the company. And so that is just about a year and a quarter is how I think of that cycle. And so I break it down based on what type of cycle we're in, whether it's the fund or the media.

01:22:54 And so give me some of the learnings from the first year and a bit of the media side. Again, this is me trying to get some golden insights out that I can steal. Yeah, well, we can jam anytime too, separately. But it was a super insightful year. We acquired a company, so actually went through the integration of an acquired company process. So all of the different operations, all the different assets of

01:23:22 shifting that over to our existing company and then the messaging and taking people along for that journey. So that entire process was a big learning. hadn't been part of a media acquisition before, so it was really interesting from that standpoint. And then a big other takeaway was really the focus shift from quant to qual. Having a background in such heavy quantitative marketing, I'm much more accustomed to having data at my disposal for things and leaning into data a lot heavier.

01:23:52 Granted, when I'm consulting with startups and so forth, it's a lot more qualitative in nature. So, I do see both sides of the coins on that side from that lens and from that role, but this is much more heavily qualitative in terms of the feedback loops that you get of brand perception of content. Content is, as you know, you get so much feedback from.

01:24:15 people writing back to emails from comments, like those are all feedback loops. So I'm always trying to internalize and draw those parallels back and almost codify that qualitative feedback to understand, you know, how can we better serve our audience with the type of feedback that they're providing and how can we adjust our content accordingly? What is that brand perception? You know, was that an event in person last week? And so you get a good sense for that shifting brand perception from people's feedback in person too, and just how they talk about it. So I'm constantly just

01:24:45 observing and internalizing and again codifying what qualitative feedback we get to try and not to try and quantitatively capture it, but to better understand the patterns behind it. That's really the key, the patterns to the qualitative feedback. It's a constant challenge to try and measure ROI of

01:25:14 this type of content because it's as we all know, but the buying journey, think Dream Data, the latest stats is it's like 270 odd days or something like that. And no attribution is going to capture that full 270 days with absolute clarity and visibility. the value of content we know is in, think Chris Walker calls it the dark.

01:25:42 dark social or dark fun or whatever you call it, which is the stuff that you can't see. It's the, I was watching this episode of this and you, they ping it on WhatsApp. We can't see WhatsApp. We can't see people's internal Slack messages. So it's really, really challenging to measure the ROI of this type of content. And it's a constant challenge of how to your point, which I love, I've not heard it called that or the codifying, try and codify some of the,

01:26:12 qualitative feedback to give quantitative data points. And it's something that we're constantly challenging ourselves and constantly trying to think of a way, like looking at expanding the funnel from like pre-MQL, can we try and visualize pre-MQL funnels? So it's like total eyeballs and then how many eyeballs we're converting to brand.

01:26:41 impressions or visits to the website that are from more owned channels and things like that. So we're trying to visualize like pre top of funnel, like really, really top of funnel awareness. yeah, we tried to codify things. It's very, very challenging, but I absolutely love the challenge because if we can find a measurable coded quantitative way of measuring.

01:27:10 that sort of value that we're providing and aiming to deliver, that's like gold. And I'm looking forward to the point at which we, for ourselves, because it's different for every company, we find that perfect solution for measuring the success of this value led, this demand gen, this demand gen sort of strategy. But yeah, I mean, I could talk about that all day, but we're to talk about the learnings and the career and things. So you're obviously still in role.

01:27:39 It's been about 18 months, so I don't need to ask you about what you left. But I can certainly ask about, I guess, your plans in terms of the next 18 months, three years, five years. Everyone's got that like one year, three year, five year goal. So what are your plans in terms of where you are right now and what you want to do? Yeah, great question. And you're right, I don't plan on leaving.

01:28:09 So the goals are to really build GTM now into media empire. So we've got an incredible media brand. We've scaled it, you over 50,000 subscribers and really quality people over 50 % are director level plus, but we want to take to the next level. So we're actually hiring right now and bringing on a team member to actually help with that process and really take it from media brand with great assets under it to media empire. So that's the next kind of 18 months there on the media side and then GTM fund.

01:28:38 I'd say I'm cheating on the 18 months. It's a little bit longer than 18 months, but the plan is to build it into a multi-generational firm, tier one firm. I love the whole, the goal of the media empire. think you touched, you mentioned the Stephen Bartlett and I think he shares a lot in his Behind the Diary series, which I watch and there was a story recently of him turning down the, what was it? The 100 million.

01:29:07 offer and them believing that they could do better themselves and ultimately long-term make more money, which isn't necessarily the primary goal. yeah, that whole... I liked... Oh, sorry. Go for it. No, no. Go on. Go on. I was just going to say, I liked how you framed it to around the audience. was really, we retain greater control over the content that we can produce, over the creativity. And thus far, it's led us to this point.

01:29:36 And they've grown and it's, Hey, we don't want to actually sacrifice that. We want to be able to retain control and be able to serve the best possible content. So I think they did a really good job of framing it that way. Obviously the monetary side comes with it too, like you said, but I thought they tastefully framed it and is a very true part of it too. Yeah. I think from a, from a CEO point of view, he's not CEO anymore. he? Cause he, I think he's got two CEOs, co-CEOs or something.

01:30:03 But it's really, really interesting watching him hire for the company in terms of the roles that he's bringing in. He always talks about the role of a founder is actually being a very good hire of people that are better than you, that Phil Voids, Phil Capps, which was a Richard Branson tip or something that he gave in his book. But it's really, really interesting. I love the whole media empire vision. I think that's an amazing vision to have.

01:30:30 It's still relatively early days in the B2B landscape for building that type of sort of media outlet, that media empire. So all very, very interesting stuff, very, very exciting stuff. And hopefully something that continues to grow and develop in the B2B industry like it has done in B2C or completely different industries altogether. Okay. So we typically finish off these conversations with like a round up, some quick fire questions to, I guess, summarize some of the

01:31:00 highlight tips and tricks that or tips insights that we've touched on over the last 90 minutes or so. So the first question would be the top three tips you would give someone looking to progress in their career.

01:31:14 Top three tips for anyone looking to progress in their career, proactively follow your curiosity. And I emphasize proactively because oftentimes we do, or at least I've kind of observed when people wait in a role for something to come to them. Whereas you really do have to go out and kind of find it for yourself. Again, always think about it or the way I like to frame it.

01:31:39 from a framework perspective is two parallel tracks. You've got all of your learnings within your kind of role itself. And then you've got an entire track that you can shape however you want proactively. So go out, follow those curiosities that will in turn help the other track and ultimately they will converge too. So definitely run them in parallel proactively, follow your curiosities. Don't necessarily follow the external things like we talked about around.

01:32:08 salary title, those are all extremely important things, but think of it from a long-term investment perspective to around rather than the short-term incremental, what's that long-term investment in myself? So that'd be number one. Number two is when in a role, think about it from a people lens. So your role isn't to check that box and fulfill your task list, it's actually to make your manager successful. So if you frame everything around that, it's going to help

01:32:37 provide that North Star around everything that you're doing. Does this help my manager be more successful in their role? Because their role and your role is designed around the organization success. So inevitably, if you are making the person that you're rolling up to successful, that is facilitating the company's and organization's success. So focus on making that person successful. And with that comes all the practices around doing good work.

01:33:06 but focus on the person. And then third would be build your network early. So I think this kind of parallels the first one around following your curiosities because network will naturally come out of that if you follow your curiosities, oftentimes, at least some of the curiosities. And it's a lot more impactful when it happens organically. So again, going back to that dots connect and retrospect quote of it's crazy to look back and you know, people that I

01:33:33 I met and interacted with for entirely separate things have now kind of come and become these nodes of my current career and area and have had an impact that I would have never expected them to have an impact, you know? And have been extremely supportive and vice versa. And so you just never know in the moment. So definitely invest in your network early with the best of intentions, always leave with value and it will kind of...

01:33:59 perhaps in turn help you in future and otherwise you're surrounded by incredible, incredible people. And sometimes that ends up helping and supporting outcomes. I love the, I think my favorite of those is the, is the first, the follow your curiosities one only for the reasons that we discussed previously. think curiosity is a superpower. So definitely, definitely follow the curiosities as you said. And I think you mentioned in your notes, even if you don't see where it leads. even if it

01:34:29 You can't quite make sense of the curiosity. Don't be afraid to follow it. Now we tend to get the same answer to this question, but we ask it anyway, because I think it is good. So do you get any career or do you have any career regrets to date? I'm curious what you typically get. I'll share mine, but I'm curious what you usually get afterwards. So yeah, answer is okay. Perfect. Perfect. I don't have any regrets because ultimately.

01:34:57 The decisions that I made along the path were all nodes to get to where I am. And again, if you do them intentionally, they all shape, they're all data points, they're all experiments, they're all interesting experiences. And think a big part of that is to focus less on the outcomes in a way and really enjoy the experiences because that is life. That is your career and really soak up each experience as they come. So I don't have any regrets. The only advice I would give myself at an earlier stage in terms of something that

01:35:27 would have been interesting to do earlier. And what I would recommend to people, though it isn't a regret per se, would be to get your hands dirty and build earlier. So I was pretty curious and focused and used academic as an outlet for that and a source for that, because it was what I was familiar with. And only later did I start building myself, coding myself. And it would have been interesting to actually try that earlier in my career journey at a younger age.

01:35:56 The answer we typically get is no regrets So similar similar answer, but I like that you followed it up with you don't have regrets because of X Y & Z and then the advice and I love the bits of advice in terms of I think there's so many people that I've engaged with in my career I've worked with that are that say a lot but don't necessarily do a lot and I think there is an immense amount of value in just doing

01:36:25 There's loads of phrases or cliche sayings about done is better than perfect and don't let perfection get in the way of execution. But just building something and getting your hands dirty is one of the best ways of learning. And as we've discussed in the last 90 minutes, even if it doesn't work out quite how you thought it would, or even if the career move wasn't what you hoped it would be, and the grass wasn't greener, you now know something you didn't.

01:36:54 before, you now know something that you don't want again, a industry that you despise and you thought you'd love. You realize that the money that you moved for is actually causing loads and loads of stress and the pressure is just not worth it. even if those, I think Matthew McGonaghy calls it sitting in the mud, which I love. And he says people should get more comfortable sitting in the mud. And I think people should get more comfortable.

01:37:22 in you couldn't get your hands dirty and it's all linked to that mud sort of metaphor, but there's nothing wrong with sitting in the mud. Like you can get up and get out of it and move on. I think people should be less scared about failing and less scared about something not working out. Yes, life is short, but would you rather try something and fail and learn something or never ever try and wonder? I think yeah, some great advice there. We've already

01:37:52 touched on the what's next, what's the next step in your career ladder in terms of building that media empire. So I don't need to ask that question. But I will ask the final question, which is, do you have an end goal? I call it the, do you have that top of Everest, that top of the mountain that you're striving for, you aspire to? Yeah. An interesting question.

01:38:18 think it's not a singular peak. So there's no Everest because often, like I mentioned before, the way that Everest are created are often external. So they're often based on things that we see externally, titles that we see, salary that we see, which may not actually align with that internal. So I'm less focused on a singular peak. I'm much more focused at the intersection and triangulation between those three.

01:38:45 three things that have always been a constant and I believe will always be the constant. So that's innovation, education and community. What that looks like from an end goal perspective is again, I wanna build a media empire. I wanna build a multi-generational firm with GTM Now and GTM Fund. And then the areas around those three nodes may branch off into singular kind of areas and almost create greater depths and greater experiments around them. It may be that, you know, it's some kind of intersection that joins on. may be that

01:39:15 you're going down a singular node, for example, I've got a lot of ideas around the education system and kind of different ways of approaching different parts of it. And so that could be an interesting area that I go down or maybe, you know, it's community also, maybe it's tacking something on and building, you know, on top of the, the platforms that we have across GTM fun and GTM now. So I'm pretty open-minded. I've got a lot of ideas, but right now I'm very focused on GTM now GTM fun. That's not changing. I'm very open to.

01:39:44 kind of developing greater depth across those three nodes, innovation, education, and community. So for example, greater depth around innovation, which actually encompasses education, could be more of the impact investing in the education space separately, personally. So that's an area I'm really passionate about, especially globally. Or it could be, again, like I mentioned, I've got a lot of ideas around the education system. So that could be a bit more of an intersection between education and community. So there's

01:40:13 different ideas that kind of float around these three areas, but I think those will always be the constant. If I think about what my Everest is, it's that. It's solidifying that triangle and having as much depth around that triangle and as much impact around that triangle.

01:40:31 I'm just, there's a, something that I think would link really nicely to this Venn diagram you keep talking about with the, the education. I'm waving my hands here, but. Yeah. Have you heard of the Japanese philosophy of Ikigai, which is the, yeah, the fulfilling and balanced life. And the reason I was getting up is so I don't absolutely butcher the four things, but it's basically like a, the balance of four things.

01:40:58 which is their meaning of living, which is the balance of something that you love, something that you're good at, something that you can be paid for and then something that the world needs. And I think this, it kind of reminds me of that, your three things of what the world needs is the education, what you love is those three things that you're combining and what you're good at is the building the communities and providing the education and stuff.

01:41:26 Yeah, it kind of keeps reminding me of that Japanese method of methodology of Ikigai, which is a balanced life, which I love. Yeah, well, I almost think of that as a layer on top of. So I think of it as a triangle, a triangulation between these three things, innovation, education and community. And I think of Ikigai layered on top of that, where it's it may be that that is more of a singular role. It may be that I'm involved in things that aren't, you know.

01:41:56 paid. It may be a nonprofit, for example, on the side of that. So maybe that's less layered onto the entire Venn diagram, but it will always be some kind of composition around Ikegai. No, I love the, like I said, this whole like combination of Venn diagram thing, data points, whatever you want to call them. Well, that's been a fantastic chat. I'm glad we ran slightly over to cover off the last few points in more detail. But I appreciate you.

01:42:25 Appreciate you jumping on with me. think this is episode 10 of season two. So this will be the final episode of season two. So for those listening or watching, I hope that you have found this episode very, very useful as well as the other nine that you have hopefully watched in this series. But thank you, Sophie, for joining us for an episode. Thank you so much for having me, Jamie. It's been a pleasure. really enjoyed our conversation and hope it helps and form other people as they advance through their careers. And as Sophie said, hopefully this will help you sort of.

01:42:54 progress in your careers, developing your careers, and we will catch you in the next series.