Stop Copying Outlier Startups: It’s Killing Your GTM

VCs, founders, operators. I think there's an absolute black box between your VCs and your operators. Today we've got Stefan jumping on. He's built and led partner programs at multiple unicorns like Pigment and Salonis. Most recently worked with founders on go-to-market at CG Partners. Today we unpack everything that changes at different stages of those growth journeys. Biggest mistake, I think, as a founder, and I think it goes for bootstrap businesses, VC partners. businesses, services, product is the fact that... What would you say in your eyes is the biggest disconnect that you see between like what investors expect and the actual execution of revenue activities? VCs and there's operators. I think there is an absolute black box between your VCs and your operators. How many times in my years of being an operator did I ever have a VC speak to me? Never. Anytime I see you in the office asking, interested in how the business is running, actually no. It's only fed through the narrative of the founder. Never. So it's a complete black box. I would say that I'm not for everyone because there are exceptions, but for the vast majority of you, do they actually have any idea what it's like on the ground as an operator in their portfolio? I have no idea, personally. What about the funds that have operator backgrounds? Because there are a few, right? Again, they sit on a board, engage with the founder, and the founders are often, again, not every startup, absolutely not. They're simply tightly controlling the narrative that was up to the investors. You know, about the revenue figures or about churn and headcount. It's like it's all really kind of, it's microscopically managed so that I can manage the expectations and the narratives towards the investor. I have so often seen such a disconnect, massive disconnect for like what it feels like on the ground, what the traction actually is on the ground versus a kind of VC narrative. And it's just... And often you get this kind of this artificial inflation of like pop-down targets. It's like, oh, maybe you're 10 million AR and VC's like, yeah, like to be in top of 40, you could be 50. And it's like, all right, suddenly targets are 50. And, you know, often, and especially scale-ups, there's hardly any kind of bottoms-up planning that gets any merit relative to what's top-down. And it's arbitrary. And I think... Is it arbitrary? Don't you feel like a lot of VCs are now starting to use... real data to derive that? Or would you say that it's still... Not that I've seen. Not that I've seen. No, I've seen. I still think it's arbitrary. Yeah. I would say there is an absolute disconnect between operators. Like I say, until I really started to do my own thing, I think I'd maybe never spoken to a VC. So maybe 10 years of being an operator. I don't think I'd ever spoken to a VC. But do you think that's a factor of like... the whole triple, triple, double, double mentality where it's like, hey, okay, for you to be the next whiz or cursor, if you, I mean, I don't even want to use that example because I feel like the AI multiples are through the roof. So like no one knows what good looks like. Yeah, the point is that a comparison thing, you know, it's like, yeah. Yeah, we're focused on outliers, constantly focused on outliers. And it's such a paradox. It's like, hey, I just see VCs like, oh, I want to focus. I'm only investing in outliers. And here's how you identify outliers. I was like, all right, so you're focusing on outliers, but you're telling us there's a repeatable methodology to have an outlier. So if there's a repeatable methodology, it's a complete paradox. It's just proliferating this kind of BS. And it's like, no, I admire, I appreciate, I have nothing but respect for these incredible companies. companies and outliers but I don't think it determines what success looks like for me. Yeah. That's not how VC's operating right because the system is such that I need to invest in businesses that can return a fund and so economics of it are such that I need you to do this and this and this. Can you do this and this and this? I need to like buy the buy and so that you feel it as an operator you get this kind of artificial and arbitrary kind of target setting and things you're going well where the hell did that come from? And then you get people that are hired on the base of arbitrary targets and are fired on the base of arbitrary targets. And you're just like, it's a very strange setup and a lot of scale ups, to be honest, as an operator. And for some founders, think about it like, you know, we all know this game, which is I'm a founder. I need to kind of BS a bit and lie and inflate to be able to raise. The VC knows I have to do that and I'm going to discount it anyway. So, but then the operators are just on the ground, just being real, just being real, just trying to just, just, just with just doing the best they can in their individual work, in their individual role. And they're subject to this weird dichotomy, which is, you know, a very precarious control of the narrative that goes up to VC. And a VC doesn't have any visibility on how the operators are actually operating. So it just feels like this big black box disconnect. And as I'm saying, it's weird. Like I had, I had never spoken to VC. And it's not like... And I'm not saying that they should be in or in the office every day, but over 10 plus years, I've never even saw one. 90 plus percent of attention goes on to this outlier. And it's like, actually, well, look at this company, one to 200 million in a year. That's the benchmark. We need more of that. Well, that's a fund return. We need more of that. And the reality is that most people building businesses, that's not what is possible for them. Tell me from your perspective, do you have a view? Do you think there's a disconnect? Oh, hugely. But I think I'll start at the tail end of what you were saying, which is it's sad because you have a lot of really talented operators. Now I'm biased for commercial operators. So anyone in like the revenue functions who have been burnt the last 18, 24, 36 months because of poor play VC. There are countless examples. I saw that there was a startup and they were doing really well. I think there were like 50 mil or something. And then instead of. being super open with their company about wanting to sort of like take the exit. It just, the founders bounced, took their cut on preferential shares and then left. And it's funny, I had a guest on day before yesterday who said he joined the startup, spent about a year and a half there. It was probably the most promising team you could assemble and value proposition slash thesis statement was as on point as it could have been. But then most of the good people left including him just because there were a lot of sort of mismanaged expectations around even the nitty-gritty of how were the shares pool structured and what they were promised over time of like even if we don't sell the business or IPO which obviously is very small statistic of companies that they exit and so what this points to is like this really hardcore due diligence from the candidate side in Rightfully so to say, hey, okay, like when I am talking to a startup, I need to be very, very crystal on how I manage their expectations and how they manage mine. Because I like, obviously no one wants to end up in a situation where it's a failed hire. But more importantly, this is someone's career, right? So I think it's even easier if you're experienced like you or some of the other people that we bring on the show. But imagine you're the first SDR. It's like, well, what should they know before they start interviewing? I actually think one of the most common ways founders mess up on the first hire isn't necessarily to do with comp or, you know, knowing, like, I think it's because they have this candidate profile in their head, but they don't fully define what that should look like over time and then be harsh with themselves of what are the must haves versus what are the nice to haves, right? Let's say you're the early hire at a startup today. So knowing what you know now, what are some of the first few things that you do? when you join a new startup on the blocker. So earlier in my career, I did get the advice, which is, hey, if you go into a business, any business, regardless of the maturity of it, always ask yourself, how does that business generate value? And where do you sit in that value ecosystem? So what's the value that I'm expected to bring to this business? And how is it generating value itself? And that was kind of like just foundationally. How does it make money? And how do I help that process? Now, depending on the maturity of the business, every company has their own circumstance, their own context. That's why. I can't, I'm not going to give anything generalized BS because a series A business VC backed sitting in Europe versus, you know, bootstrap business out in the Philippines, you're going to be... you're going to be met with a different circumstance and context. So what is the maturity? I've been looking at, right, what's the state of our revenue? What's the state of the product? So I go, right, let's go to product. Let's go deep into what's the differentiation of it? What's the value proposition of it? Where are we in terms of traction? How much revenue do we have? What are the customers like? What's the ICP? Do we have a clear thesis on that? Is it proven? Because we always talk about, especially if you're in a venture-backed business, everyone wants to go for scale. It's like, yes, we'll build for scale, but to do that, we need to build repeatability in our revenue engine. And to have repeatability, we have to have some kind of measurable driven proven performance. And more often than not, when you go in and it's early stage, you're not repeatable and you probably don't have it proven out yet. So it's about, well, how much fraction do we have and what's the delta to scale to a point where we can actually start to be repeatable. And so these are the kind of questions I typically go in and ask is very much being a listener because nobody has been. in that business at this time. Let's maybe zero in on the few startups that don't have a fully developed sales motion. Let's hypothesize that they're now starting to actually develop like a real go-to-market engine where they go out and win business. If you were like the first commercial hire, let's say under 10 million in revenue, what do you think are sort of the characteristics that set you up for success in that kind of setup? Deep understanding of what you're selling. hypothesis on your ICP and the speed at which you iterate. That speed of iteration I would say is more or less the recipe for the success because again nobody's built what you've built in this moment in time but when you look at the ICP you want to want to narrow it down as much as you can to the minimum size of which it can be repeatable because you want to get the compound benefit so that every customer can potentially bring on additional customers you've got one story compounded into something else the last thing you want is just just is yeah sure you can be scattered on if you've got no idea but that should be your first hypothesis if you even pre-revenue should be on the on the product on the differentiation the pains that you know that you can solve and where it's differentiated and then create a thesis of which persona can it help and talking obviously from a b2b setting not necessarily b2c but the persona for the size of the company which geography am I targeting which industry which segment and I just try and narrow that down as much as possible so that it gives me the the best chance then create repeatability that's right and when I say you know the speed of iteration is that we have to know if it's working or not and the first thing is like my message market fit so if I'm doing outreach whether it's okay it could be could be content I'm pushing out it could be just kind of outbound it could be networking it's the message that I've curated on the solution pain fit resonating and you'll get a sense now in your conversion if you're not converting into even meetings booked or on no matter how you're outreaching then then maybe it's the message. Gotta go back to the drawing board. Yeah back to the drawing board. And if you're getting the meetings and it's just not quite resonating or they don't hold budget or the pain isn't quite there, then is it the persona? So it could be one of a myriad of things. But let's say like, and I'm someone like I'm culprit, I'm not going to stand and say, hey, you've got to measure everything. No, I don't have time for all that admin when I'm really early. But it's something that's often I think about all the time. It's implicit. I have in the back of my head, I'm like, look, this message market is quite right. We have to evolve the messaging. not have some rudimentary stats on like what are reaches, how many meetings that I plan to get. So I have a sense of whether this is working or not. And I always have to have a sense of, is it working? Is it not? And then iterate, iterate, iterate. And I'll be honest, like either being a full-time employee or working early stage at business, I have not yet seen one that has hit it one for one. They all have a plan of iteration. Narrowing your audience. to the minimum amount so that it becomes repeatable. It's always super tempting, right? It's like even me sitting here recruiting for software startups, like what a big time. So if you think about like where you bring the most value, that's when I started going to the drawing board and saying, hey, actually, you know what? We prefer to work with software startups that have some sort of vertical application because then they go deep into that specific sector or industry. And I feel like a lot of startup founders, they fall into that trap right where even if they're somewhat agnostic they forget that you know it might be wiser to start with a smaller audience and then expand from there yeah being opportunistic is great right when you're early being scrappy has to be with intent with intent is exactly you said for yourself it's like i'm sure you'll have geographies you focused on or jobs you don't focus on i'm sure you'll have verticals that kind of work better for you than others. Even for us, it's like when we started doing some, let's say, advisory and services to early stage companies, you know, what we do to support a business if they're, let's say they're VC backed and they're Series B or C or D, it's way different to what we'd be doing if they were a C business or a Series A business. We can help companies with certain functions of the go-to-market if they're more mature, but we really like doing the kind of holistic. go to market build at the early stage and we're like, well, we'll never create repeatability in our own business if we just keep scatterganding a lot of dabbling about this, about that, about this, about that. So you have to kind of question what kind of business are you wanting to build? So if you're planning to make it repeatable, to make it, then it's really about just doubling down and focusing on nice feed that works. What's another? common mistake that you see founders make it could be through the clients that you deal with now it could be from the past like what do you think is like a really common one that people tend to overlook tons of mistakes you can make i've made them most of the business have made them and it's about okay is there one that's maybe generalizable enough biggest mistake i think as a founder and i think it goes for bootstrap businesses vc businesses services product is the fact that the comparison is a thief and joy The moment that when you compare yourself to other businesses and it ceases to inspire you, you have to stop comparing. And the amount of times I've seen business owners compare themselves to another business influences the decision making irrationally. But this company is doing this. So this is how it should be. Oh, I've had advice from a guy that worked in a company 10 years ago that did this. I should do this. It's like, you know, the balance between being inspired. and taking inference from comparison to then ultimately influencing your decisions is a really fine line. And I think that the amount of times I'm speaking to founders. It's a really good one. And honestly, like it's something that matters so much because we see, you know, this is the reason you're doing this. You look on LinkedIn and I understand it. I totally get it. And I advocate to a degree. Look at the messaging that gets put out from. from the network, from the ecosystem. The reality is, is that I see outliers generate about 90% of attention and it's not repeatable. The circumstance that has often made these outliers successful is not repeatable. And we try to make it so, but the rump and the majority of businesses that are operating, these outliers hold no relation. They have no comparison that's useful and they often influences. And companies I use and I love and I've got huge admiration for Cursors and Lovables and amazing companies. It's what they did. So this is what I have to do. They're so different. What they're building is so different. The product's different. Where they're building from is different. It's absolutely no relation. Often I've seen it with founders actually influence their operational decisions in a day to day. I'm going, you know, yes, I've been inspired to take appreciation from those outliers. But this is the narrative that I'd love to see change, which is I'd love to see real thoughts, real businesses that are outside of those outliers, that are the rump, that are building without a tailwind, without a headwind. The majority are building without, they're just building and the majority of spaces are in neither this headwind or tailwind state. And I think that... Stop comparing. You're on your own journey. You're on your own circumstance with your own context and nobody's built from where you are, what you're building, whether bootstrap, whether VC backed, whether, like I say, even we're celebrating all of this investments and fantastic. That's just resource allocation. Let's celebrate outcomes. I don't care where it comes from. I don't care if businesses, again, bootstrap, service, product or otherwise. Your success is not determined by comparison of an outlier. Your judgment of success should be your outcome. There's a fine line between comparison and sniping good ideas, right? Like everyone's talking about cursor lovable. And I think there are some fundamental, I would say, tactics or strategy that you should take away as a founder. For example, be very vocal about the brand that you're building and when why the value you're bringing to customers is there. I think Anton is a great example of that. Right. If anyone you speak to from at least from my network that I've seen, it's one of the first things they say that's great about him. And I think that in founder led, like you've got to be relentless with how you message because no one's better to do it than you. But I'll agree that oftentimes we see far too many occasions where the comparison brings them down. One thing you think founders should push back on more to their investors. If they feel that demand is. irrational, irrational or unfair, push back and protect your people a little bit more. I don't know exactly what that will be in the circumstance or context of the person or the business, but often again, VCs are kind of often trying to help in a way and they're trying to get through different ideas and often they can say things that are kind of uninformed and they'll expect things that are not fair. And I think that often I see founders are a bit timid or they're always scared a little bit. cautious around the VCs and we'll just kind of be there'll not be a filter to the operators underneath they'll just pass it right through oh VC mentioned partnerships the channel we should look at right right you know we've got to figure out I need a clear plan as to where we're going to invest what why partnerships are going to work we suddenly create a lot of work I'm like settle down settle down like it's not it's like what can often be a conversation turns into a huge amount of work as operator and I would just say like you know put your people first, put them first. And it's really really important because we're the people that are working, slaving away to build the returns for you guys and you know we don't need a lot operators, I'll speak on behalf of many, it's just a little bit of courtesy. I spent way too much time building board reports and board decks and intrusfah way way irrational. I need a number on the addressable market for partners. I don't know what, I just need to be big. Just make a big number and give me a lot of logic to it. It's not going to move the needle with any performance. It's going to spend hours doing this, waste of time. And it's all because they've asked about something. That sort of rubbish. Just be a bit of a filter, push back, have confidence and trust that you can push back on sometimes unrelated demands. And if you're an investor, biggest piece of advice I can give is if you're genuinely curious on a topic or a function or in a business and you really care, just invest a little bit of time. Just go and ask. Say like, hey, I actually am curious to say we're probably partnerships. Yeah, maybe I'm going to have a chat if you don't mind for half an hour, an hour with the partnership team. Or maybe I can come in and spend half a day with the team because I'd love to understand, like allow a little bit more connectivity. Funny, we're talking about trust and we're talking about knowledge flow. And there's just something that's facade. narrative stab exists in around the founder and VC and the board. And let's break that down a little bit. I think that one of the things that founders talk about a lot, but maybe don't necessarily follow through with in all scenarios. So again, there are always exceptions is opportunity cost. I think as any good salesperson, even if you're a technical founder, the big question you should always ask yourself for every decision that in some ways impacts more than just your scope of work is, what's the opportunity cost right like but bringing that back to hiring i don't know if you've seen the same thing but recently we've got what we've coined as the founding account executive or the pioneering sales hire we've got founders hiring associates and chief of staffs which i i think these are all actually part of sort of the revolution behind let's keep teams lean and small so i'm all for it In general, like, would you say, like, when you're coming in that early, how do you know what the right motion is? There's so much noise, there's so much distraction. Where would you start looking if you come in and sort of the motion isn't fully defined? If you go even one step behind that, I would say you want to stretch being founder-led as long as possible. You want to really stretch yourself, maximize as much traction. Because I always talk about this founder's margin, which is that, like, if you're even outreaching as a founder, your reply rate will be higher. your conversion would be higher than if you were just a first employee. There's always a difference. You always get this margin. So you want to just take advantage. You said that yourself, and I completely agree. Like the biggest and best advocate for your business is your new founder. And they should push that, push it, absolutely leverage it. I think that when you go into a business as a first hire, depending on how much traction that founder's had, then infers. what I'm going to be doing, right? Because if you're going in really early because the founding team doesn't really have the go-to-market expertise, you're actually having to lay some more foundational decisions and frameworks early, such as maybe even creating the first thesis on the ICP and actually doing the first outreach and creating the first meetings and pulling together the first revenue. But if they have that traction and they have their 300k or whatever it is in traction, for me, it's all about, again, how do I go from being... measurable into being repeatable. And I would just be focusing on what works? Where is our revenue coming from? That's the first thing I always ask questions. So we generate this much revenue. Where is that coming from? Why are they buying? What is that ICP? How have you been converted? How have you been outreaching? And I like to just focus on what's working and then see what other opportunities. Maybe there's opportunities to exploit additional content lead marketing. Maybe there's additional opportunities in partnerships. It's impossible to say that for me. That first commercial hire should be asking those questions. It's about, well, what works? Why does it work? And how do I create repeatability in it? That's very simply what the remit is. How you do that is completely dependent on where the business is about. Yeah. Talking about partnerships, I mean, you were part of the early days with developing that out from an alliance perspective with two very successful companies that I'd say pretty much cracked the code in some ways. Maybe a good place to start is like talking in the context of both. the softwares that you were representing, right? Like enterprise heavy. Is there a signal that says, Hey, it's the right time to start looking at partners? You can't sell your product yourself. How can you expect someone else to sell it? Simple, right? Some spaces lean more nicely to partners than others. I will give examples. So I would say that once you have, I would say your product market fit, once you have that, what described as that kind of measurable performance improvement. I guess, yeah, measurable performance. I would always start to look at, right, who sits in my adjacent ecosystem? So I mentioned the CFO's office, or let's say Pigment, let's say I've got a planning solution, but maybe, you know, we sit really nicely next to month closed solutions, sit nicely next to treasury solutions, we sit next to, you know, on top of the ERP, we sit with the technology ecosystem around us, it's really nicely complementary, we're sharing a very similar ICP. So there's quite a nice opportunity to bring some from mutual business right depending on the partner motion i would always say you have to have a direct sales channel if you're looking at this kind of referral or co-sell business especially technology partners you want to build a two-way motion because otherwise nobody wants to just have a feeder on their books and i'll talk to that um you know in the case of solonis you know we're selling it to these large enterprises and i would ask the question and i guess this is one of the foundation let's go back to the beginning for what when i should partner is that how do my How do my buyers buy? How do they buy? And what are they buying? And what are their problem statements? And take the example, I'm a CFO, let's say Siemens, massive conglomerate. I don't care. A salonis, a ServiceNow, a sales or individual vendor. I've got foundational problems like or challenges, profitability, cash flow optimization, working capital optimization. I've got foundational kind of challenges as a CFO. I'd like to know the role of people, process, technology. How do the vendors roll up into helping me address these big, big, big ticket items like profitability? Now, who do I turn to when I want to talk about or spar soundboard this challenge I have as a profitability in my business? There's no single vendor I turn to. I'll turn to my trusted advisor. Maybe it's McKinsey, maybe it's the big four, maybe it's Accenture, maybe it's one of these guys who can help and talk to my business. right across the they've got the domain expertise they know my business intimately they understand the technology landscape they understand my systems and processes they can really talk to me and start to think well what are you trying to do and often what we saw is there was the the seed of the finance transformation that's what we would see and we're like all right okay what happens is i was like well how can we make it that we are like the number one tool in their toolbox so that when they're having these conversations with cfos that we're part of that narrative. We're part of the fix. We're part of the future, part of the transformation. Because if we're not partnered with them, we're not part of the conversation. And the hardest bit for us is getting a seat at the table when we're talking to these large giant enterprises. So for us, that started really early and it was a nice compliment because in and around an implementation, it's not just technology implementation, it's all the advisory and enablement and services that goes around it. And it's a kind of longer term engagement, especially these large enterprises. So for us like that, we could have engaged with that really early and we did. And so there's, I would always say is like who you're selling to understand how they buy and the art of partnerships is really about building incentive alignment. Why? Why would too often I get people going, yeah, partners, what's the purpose of partnering? To bring pipeline. Oh, red herring. Nonsense. It's nonsense. It's like, yes, that's one metric. One metric is the source pipeline. And then often we'll say, I want this technology company because they can bring me lease. And well, yeah, but what are they getting? Really? Do you think they'll change the behavior of their reps because they're getting 10% of a referral? No. So it's like, actually, you've got to think more holistically about what's in it for them. And that's why I always say is like there's different types of partners, there's different motions. And, you know, especially when we were co-selling at Pigment, we did this really well. It wasn't just about, you know, referring business. It was actually how does it impact our win rates? How does it shorten our sales cycle? How does it increase our average deal sizes? So we saw increase in average deal sizes. We saw reduced sales cycle length. So we saw increase in win-raise. Because what happened was these partners were a trusted advisor to their business. So when they were bringing us in, we're working alongside them. They knew that business intimately. They had the domain expertise. They knew how to navigate the procurement, the buyers and the teams of IT. And they were kind of a trusted sounding board for us. And we had a, it was just a win-win. Yeah. Could you give us an example, if you can, of like an early partner or? a few of the early wins that you had there and how you how you won them like how did you get their attention an early one with with pigment was actually with uh with with deloitte in belgium and i mean we were we were lucky in a way it was quite difficult to crack the nut that is the big four highly matrix complex organizations um you know they're already partnered with various uh systems and providers so what we found is that okay well they are partnered with lots of adjacent solutions to us like Orkiva and other tools. And what they then they were also partnered with Anaplan, kind of larger players at the time, obviously, Pigment was less mature, we were able to create an incentive alignment where we would help them segment their business. So they were looking at Anaplan and kind of enterprise space, but they had no, who were they, who were they partnering with for planning in this mid market? Not really, not really anyone. So we were like, okay, well, is there an opportunity here to service kind of less? complex environments with a planning solution for Deloitte and then for them to be able to build and wrap around services around that and then not just one solution they can provide a kind of wider transformation across different systems which is I mean for them it's a clear win. Now again obviously we were aspiring to sell these large kind of enterprises so you might on the surface go well what's the point of partnering with them if they're not actually meeting the kind of aspirational ICP that we're looking to sell to. getting your foot to the door and i see with many partners especially larger ones it's very much it's a large large lamb and expand so once you get into adult belgium you're suddenly able to speak with the uk or germany or france or netherlands and start to and start to broaden your reach and build credibility and what it did is that we were very lucky we actually generated leads they brought business to us and we converted and we won and got our first logos and they became lighthouse wins. It started to open the door to the wider Deloitte network, open the door for other opportunities and other in the big four and look at it and see. And suddenly it starts to compound. And that's what it did. And we did that pretty early, to be honest. I think it was really very early in its journey. And that was a credit for that. They didn't wait. Too often founders and businesses, they're like, ah, I should really think about partnerships because every time I'm in sales cycles, you know, these partners are involved there. Every time RFPs are written, it feels like they're written for some of us. I'm going, yeah, probably. Figment wanted to get ahead of that. We're like, hey, well, actually, we know the space of planning as an older software space is well-known, well-defined. There's an existing partner ecosystem. We're kind of plugging into an existing ecosystem, and we just did it very early. With Solonus, a completely different ballgame. We're building a category from scratch. I mean, when I first joined Solonus, it wasn't even as early as Figment. You talk about process mining and what's that? Firstly, I don't have a clue what process mining is. And then asking a budget for a technology I've never even heard of. Even though it's great, I'm like, it's completely different. And that was the same for partners. Partners, there was no such thing as process mining as a category. So for us, it was a massive front load on education. And the partner play probably took a bit longer to get to the maturity that Pigment did in relative terms. But then we had a bit of a domination of that space because we were the kind of really the main competitive vendor for a long time. I'm not one to preach for frameworks, but do you have any? Firstly, partnerships shouldn't really just roll up into sales. Partnerships is its own function. Partnership is the most cost-functional function across the business. Engaging with product, marketing, sales, everyone, professional services. The reason I say that is you have to have exact buy-in. If you're in as a first hire, why are you exacts wanting, what are they wanting for partners? And it might be an education play at the beginning because often they're saying, okay, I want pipeline. Especially if you're in a new category as you start, right? It's like you have to build the right expert. First thing I'll do is get alignment with your exacts and ensure the right education and understanding what's possible with partnerships. That's the very, very first thing I'll do. I couldn't stress it. It's more important. And from there, once you understand that, like there's different. it's educating them but there's different types of partner so I can have consulting partners with like boutiques, RSI, GSI, think about like a matrix I've got technology partners those companies that sit adjacent to us maybe cloud and marketplace alliance and some even look at PE as a function and it's like well I can sell to them I can sell through them I can sell with them and you just map out the matrix and start to think okay where are we going to focus because often you see founders like want a bit that but that but that it's no no like you focus on one or two and that's it that's all you should focus on to begin with. You can't put a resale motion and also why are you doing it? So you might say, I want to have a resale motion. And so you go, well, what for? It might be that you decide, okay, well, actually, you know what? We're focused on Europe rather than kind of planting our seed and spending our millions opening up in the US or maybe going out in East Asia. I want to open that market for resellers. So that's where you're going to focus on your efforts. A lot of people see it as this huge daunting task of like, how do I... approach the AWSs and the Microsofts of the world. And as you said, right, it's about figuring out and mapping out where your value add is and starting from there, basically. Yeah, look, different partners will do different speeds. And it has to marry up to your ICP, going back to like, and your ICP evolves continually, right? So it'll be different in six months, one year, two years, one. But ultimately, like, who am I selling to? What is my solution pain fit? And just understand it to a T. And then it's about what is the right... motion, right partners for us. Again, if you're selling within a specific vertical and you have a 25 person boutique that has great domain expertise, their ability to move is going to be infinitely quicker than an Accenture of the world. But you might say, well, Accenture is the long term strategic importance and I want to invest time and energy into that. But this is where I'm talking about education is really important because some people don't understand. They say, well, build out a relationship with the GSI. You're going to take a year, two years to really start to get your in and mature and build your lighthouse. These are massive lands in an expanse. But you're not going to drive any import or benefit by GSI. None. Except that is reputation. Unless you've got a buddy there that always helps. Honestly, you have to have a really, really senior buddy. Like a really senior buddy. Even then, you know, even then. So that's the thing. Really simple, exact alignment, educate what's possible, build out your matrix, align where you want to focus and create the right metrics. And the metrics shouldn't be just focused on referral. Look at what the impact partners can have in funnel, out of funnel, and then start to build your partnerships around that. I'm going to move us to a topic that I think we both have super strong opinions on. What's one operational habits? that you feel every startup team should adopt from day one? So anyone that knows me is probably going to laugh because when it comes to hygiene and admin and I am one of the worst. Operational habit. Operational habit that I wish I had would be the organization in and around my client calls and I say with potential prospects and so on. So I would say, you know, my CRM hygiene. whether it's next steps, whether it's whether it's closed dates and so on. That is super, super, super important. Now having insight from the other side as a decision maker and leader that you realize that all these raw data inputs are influencing my ability to make decisions. I need insights. I need to know what the trending conversion rates are. I need to know what products working, what markets work. I need to understand to make decisions. And I'm completely dependent on individuals on the data entry, basically. I would say from a business standpoint, I would say that fairly simple in and around sales prospect data entry into CRM is critical because the foundational piece to ultimately making any kind of rolling up to making decisions. I feel like if most of these next-gen CRMs were smart, they'd really try to productize based on the growth stage that the company is at. I think it's down to figuring out like how they can go as wide as they can to cover all the different end users, but starting with the ones that probably hurt the most. And in this case, it's almost always sales teams. That's my take on it. Do you think that there'll be any kind of verticalization of CRM? So we see it with, you know, certain verticals have nuance and different requirements for an ERP. Maybe it's the same for CRM. And I'm just thinking trend, which is we're seeing that the... the cost of building is lower than it's ever been. The accessibility to build a business is easier than it's ever been. I feel like we already have. I just didn't think about it as deeply as now because, I mean, coming from recruiting, the sort of holy grail is Bullhorn. But Bullhorn is basically a CRM and an applicant tracking system. So those are specific to recruitment. I think the really valuable nut to crack could be the migration from like Salesforce into the next generation CRM. How do you make that easy? An example I gave was like when I went from iPhone to Android, Android back to iPhone. The most recent time when I changed, it was so easy. It was so easy. They made the switching costs really easy. I literally just found that. It's actually a really good analogy. We'll just migrate your apps over. Don't worry. And I was like, imagine it's like I could read my Salesforce instance, see all the fields. Yeah, no worries. We know exactly how you're using your Salesforce. We see your users. We see the fields. We'll populate all of that for you. Boom. Like here in an hour, there's your CRM. I was like, in my head, obviously people that are more technical than me will be laughing. You know, from a simple brain, I'm a super simple person. I'm like, it's really complex from Android iPhone. It feels like. It's just tables. It's just a big database at the end of the day. That kind of brings me to my favorite part, which is let's talk real about AI. What tools are you using day to day and across like what specific? use cases i'm using granola or no taking no taking we have you fireflies sana tldv i mean i'm sure they all have very similar very competitive in transcriptions granola is just pretty seamless it's really easy yeah using lovable actually levels super like if i have to build let's say landing page or even it's just like visualizing something i actually don't a one-pager just last last week the other week and you know i'm not i'm not a designer but I find it's just a perfect bridge from like, hey, I have an idea what's in my... Yeah, sure, it's not going to be like, great, but you just completely shattered the silo that would exist between. Like, it's incredible. So, yeah, amazing, amazing solution. I use kind of, you know, OpenAI GPT for like my kind of centralized knowledge repository. I'll try to filter kind of my... funnel all my kind of transcripts everything through there and i have different folders so for different better client activity for the product whether it's like so so basically it's obviously building its own context around so i'd say kind of day-to-day those are the three three three kind of big ones um what about you though power user of gpt and perplexity both personal and professional yeah perplexity is good for like because it's built into my lemlist workflow on researching the startups that we want to go after. So it does a really good job of just summarizing like, who do they sell to? So that when I'm reaching out, I don't like I look like I've done my homework. And then I think to build a layer on top of that, we're actually using Lovable now to prototype certain ideas we want to productize now, by no means are we ready to take them into production either. But We've had already a couple pretty good responses around, hey, like normally I get sent a shit ton of PDFs on a Google Drive that I have to look through one by one as a CV and I just build landing pages for every candidate I share with a client. It's just so much easier and it's like you can skim through it in 10 seconds and tell me are the must haves there, right? So are they in the right spot? Do they have the right seniority? Are they within scope of the package? Have they got the right experience? That kind of stuff. And we've recently started building an AI native version of candidate CVs. So basically what we've tried to do so far with a couple of people is clone themselves and train a GPT to become sort of like a representation of that person so that if a founder wants to speak to a candidate without wasting their time, they could actually talk to their GPT version of the person and ask it the basics. It's a great way of filtering down. I've been around kind of... either trying myself or start up for about 15 years. And when I started, I literally had pen and paper, pen and paper drawing out examples. Wild. Wild. Literally, 50 years ago, I was at university, pen and paper sketching out. It was actually an early idea for WhatsApp, really early. I had no idea. I had no technical understanding, way out of my depth. I had a problem, which I was sitting in a university library. I was connected to Wi-Fi and I couldn't message anyone. There was no messenger. There was no WhatsApp. And I was going, this is mental. I was like... I'm connected to the Internet. Why can I not send a message to someone? This is crazy because I had no signal, but I had Wi-Fi. And so I started to try and map this out. And I went to speak to an advisor about it. And he couldn't understand my... I understand the problem. He couldn't understand what I was like, my jokes. And I was like, I have it in my head. I can't explain it to you. Yeah, no. It's never been easier. I could talk to GPT about it. I can even mock something up in Lobo. I could just... It'd be so much easier. The red herring is not all building a kind of production grade software. No, no, no, no. But I feel like the kind of silo that sat between someone, a simpleton, simple brain person like myself and great engineering is now just completely collapsed. It's unbelievable. Like I think there's never been a better time to build a company. I couldn't agree more. And I'm just going to straight fire. So putting you on the spot. Go for it. Like you're the founder of a VC backed startup tomorrow. Let's assume it's B2B software since that's what we've been talking about. Five tools, non-negotiable. What are they? Let's assume like you've just assembled the founding team you guys have just raised. Okay. Well, firstly, personal preference, like really basic. It's not a tool per se, but I'll sit on Google suite because like whenever I'm dealing with Microsoft, I think I die inside a little bit. And, you know, it just is just I think there's a noticeable friction in my day to day when I'm having to use Microsoft as a foundational stack. What about Notion? I feel like most founders live on Notion. I don't get it. I understand. I see it. I'm using it a lot. I just it's just become almost the default for like knowledge. I just I think it's just a bit too customizable for me. It's just a bit more like, you know, maybe it's the fact that I'm a bit dyslexic. It's just too much text, too many drop downs, too many clicks, too many... I'm like, I know it's a mishmash of like Word and Excel and PowerPoint, all this stuff thrown together. But if you put it down to my head today, I'd probably take Atio or HubSpot. Atio or HubSpot. I'm not married to it, especially when you're at the very beginning. The switching cost is not terrible. So I'm not married to it. Yet. Yet. Yet. You've got three more. Yeah, you've got to have a note taker. I don't even remember the last time I typed during a meeting. Actually, I've had this desk for a while and I have actually quite a number of years I've had the desk. I've got two notebooks that are still in their seal. I've never had to use, not used. um as a reminder i guess a reminder i've no pen in sight i say okay so google street yes granola okay so let's say integrate gemini yeah i'd be for sure be lovable i would say that i would say i'd encourage everybody to use that even for idea sharing between people or you've got an idea you want a website right everyone spent half an hour blah blah blah blah throw your ideas in like i i just think that that's like um it's an absolute hack to to yeah especially obviously all the time get what's in your head out there For sure. And then the last one, actually, it's not an AI tool. It's Slack, Google Suite, Slack, Granola, Lovable, and Atio. What's one use case that you think is overhyped and one that's underrated when it comes to AI tools? I think the way that you use AI is more important. I think it's great to help you formulate ideas. But like I run a like from a country mile away, I can see if something's kind of AI generated. So I would rather say that, yeah, like to have AI generated content, I would say is a little bit, a little bit overhyped to me. I think it's good at repurposing content. I had someone on the show yesterday that said that like repurposing versus replacement, right? It's very different. Like if you're going to use AI too. draft up your content is very different than if you're going to say, hey, okay, these are my ideas. It's great for like pre-production and ideation. Absolutely amazing. I think it's probably overhyped the idea that AI can provide today great quality production level content. Yeah. It's hard for me because I'm a massive advocate. I love adopting new tools. I love it. I love challenging status quo. And sometimes I see the direction it's traveling in rather than what it's capable of today because there are certain things that just was rubbish out two, three years ago. Even my initial like AI recorders were not too great, especially when you've got an accent like me. What about you though? I think underrated Notebook LM. Notebook LM will do everything from summarizing and categorizing all the files you've stored down to the conversations that you've had and in between. You can use it for research predominantly, but like, let's say you want to check if the last time you spoke to this person or you stored someone's file was within the last six months, like you can fact check that pretty clearly and show you the exact quote or source of where you had that conversation in mind from. You can also use PDFs like YouTube websites, all this stuff. and it'll summarize them and it'll actually basically i think where they want to go is they want to build a knowledge base so that as you grow your your drive that it becomes more predictive rather than reactive and so it's like oh hey nav like you watch a lot of podcasts about venture capital you should check out x person's channel it's not there yet but notebook lm for sure obviously for me someone that's always on call i can't live without a note taker so i think that one's perfectly rated i would agree What about overrate? I more specifically want to say that like all these like AI powered features behind outbound. So actual writing the copy versus giving you the basis or the signal for which says, hey, you should reach out to X. 99% of the ones I've seen are spray and pray. Like it's too easy to sniff. And as you said, like most people are a bit allergic to it. Yeah, I was going to mention that. But I think that there's going to be an acceptance. Now that where the reality of them like I think for me when it comes to outbounding tools the classic 11X artisan the kind of proponents of how you just replace your kind of BDR SDR team yeah I mean like nonsense in my opinion right absolute nonsense but I think that's pretty widely accepted now as nonsense I think it wasn't maybe six months six to nine months ago um as opposed to like Toppo and Apple Market have uh is very much BDR plus AI is a better BDR. I was just going to say, I think Dan and his team are the exception because I've worked with them and their messaging is totally different. Yeah. The messaging is on point. Like I have to say, it's a great team. They've got great results. Yeah, I just, I'm a bigger proponent of what we're advocating rather than selling this kind of pipeline dream that, you know, a BDR could take. perfectly great qualification calls if it's an AI rather than if it's an individual person that doesn't understand the context of the person building rapport because like little things like you got a call and you got five minutes with someone you'll know this right is building any degree of rapport is so so important. The last thing people want is yeah I'm expecting the fact I'm picking up the call I know it's transactional the last thing I want is to make it feel transactional and I think that that's it's it's there's an art to it. What's something you would do? to make yourself twice as useful to the business that you're joining? Yes, it's a good question. Twice as useful as a lot, right? I mean, I've thought about the career advice I'd give myself if I went back, things I might do a bit different. But yeah, I think I didn't know that the communities that existed, then go to market. There's amazing communities of people. I think in Europe, we've got... kind of a challenge which is that we really love to go on about the centralization of London, Paris and like Berlin as places to build. So I never even thought that being based in Edinburgh, being outside of these hubs, there would be the opportunities to network and connect and there'd be other people like me building and commercial. And I think that I would, you know, and I was given the advice early on in my career and I'd say wrong, terrible advice, but they were like, hey, you'll never make a success yourself in the UK if you're not in London. and I think that it starts to use like that's a chip on the shoulder you still want to win against that but the reason I give that as context is that you know I probably didn't believe there was the opportunities to network and connect with people like-minded and learn from other people that would have extradited how useful I would have been in the business even from a tooling perspective now what tools are you using how are you outbounding I had no idea how to do anything anything and I didn't really have any network and I never really spent the time to invest in network outside of the business. And I think that I would have, if I go back the very beginning, first year, first two years, I would have done that because I didn't have a clear mentor. That investing time outside would have been great. Just building your communities, building your network and just being a sponge and learning from as many people as you can. Super underrated. And I'm a very open, kind of transparent person. And, you know, I love to make people feel empowered. really really important and I think one of the ways you can do that is just with knowledge share you know I share everything with exception rather than the other way around and I think that there's a way to get people invested in and bought into the journey with wider context for the good the bad the otherwise and it's a pet peeve like people say like you need to earn people you need to earn my trust I hate that no like the moment you hire someone they've got absolutely got all trust Trust could be broken, but you got trust. So share, invest in them, invest in people, get them bought in, share with them, be human. It's free, cost nothing. It's funny, maybe you were born as a recruiter in another life because one of the mantras they preach in recruitment agencies is it's easier to break trust than to earn it. And it's true, right? We're all trying to sell something if you're on the front line. It's just about being super clear about what the sell is and if that sell is actually genuine and comes from a place of like pure value versus transactional selling. And it comes back to everything we've talked about, partners, direct sales motion. Thanks for jumping on. I appreciate you. I mean, unfiltered is what you want. So, you know, I really appreciate you having me. It's great to have the kind of open conversation and lift a little bit on what life is like as an operator underneath. Yeah, thanks for having me. Legend.

In this episode of In the Trenches, Stefan Ross (early operator at Pigment and Celonis) joins Navin to unpack what actually happens when you’re an operator building revenue without a playbook.

Stefan has been on the ground at Celonis and Pigment, navigating first GTM hires, early ICP bets, partnerships, and the messy reality between founder ambition and operator execution.

We talk about what operators see that board decks miss, why comparison to outliers breaks decision-making, how partnerships actually work (and when they don’t), and what GTM teams should push back on harder.

Chapters
00:33  – The disconnect between VC's and operators
07:49  – First principles for early startup hires
13:58  – The most common mistakes founders make
22:59  – How to crack the partnerships motion in a startup (Pigment & Celonis case studies)
34:25  – Must-have operational habits for sales
37:41  – Leveraging AI in business operations
48:22  – Advice for sales

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