Most founders think their job is to win customers. Harrison Rose thinks that’s exactly the wrong way to look at it.
Harrison co-founded Paddle, scaling it from zero to over $100M in revenue and unicorn status, before jumping back into the scrappy startup stage with GoodFit – a company born directly out of the go-to-market mistakes he made along the way. He’s one of the few founders who has lived the full arc of the $1M to $10M scaling journey multiple times, and he’s unusually candid about where things went wrong.
In this conversation, Harrison reframes what product-market fit actually means in practice, shares the painful ICP lesson that nearly derailed Paddle’s Series B, and makes a case for why AI is about to force a very uncomfortable conversation between CROs and CMOs.
These are just some of Harrison’s key insights from his conversation on our Making The Grade podcast. You can listen to the full episode here.
Q: Companies often stall around $2M to $3M ARR despite having real customers and strong early traction. What's actually going wrong?
Harrison Rose: “I think the problems actually start right at the beginning, but they just don’t properly show up until $2M to $3M. In the early days, founders think their job is to prove that someone is willing to pay for their product. They’re probably not wrong; that’s the first box you need to tick, but if they have some success, they win a customer or two and think, great, this is working, I’ll go find another person willing to give me $5k, by hook or by crook.
And founders are resourceful, relentless people, so they find a way. They get to ten customers, half a million ARR, raise their Series A, and then they think they’ve clearly got Go-To-Market fit and can just hire someone else to go do the same thing for them.
But what they fail to recognise is that as a founder, you know the product best, you know the market best, and you own the roadmap. That’s founder privilege, and the people they hire don’t have that. They can’t create pipeline the way the founder did, and they ultimately fall flat on their face.
The experience of those who grow successfully through Series A and beyond is very different. It’s not their job to convince someone to buy their product; it’s their job to find a way for others to repeatedly sell it without the founder in the room. It’s not about finding a way to find ten customers, it’s about finding a way someone else can win ten customers for you, and that’s a huge distinction to make and get right.”
Q: Everyone tells founders to focus on ICP. Why do so many still get it wrong?
Harrison Rose: “People aren’t failing because they haven’t heard the advice to focus on ICP. They’re failing because they massively underestimate the complexity and impact. Historically, founders haven’t had the depth of insight into the people they’re selling to in order to truly understand what’s different about those they’re winning with versus those they’re not.
ICP isn’t binary. Every company sits somewhere on a spectrum of ideal, with lots of different attributes carrying lots of different weights. The data points people usually talk about, such as industry and employee size, just don’t correlate anywhere near as highly as the things that are genuinely specific to your business.
What we got to at Paddle was that companies receiving a high proportion of traffic from outside their home market, especially when they didn’t support the currencies and languages of that traffic, were great for us. We could tell them exactly why we could help. That’s the level of specificity you’re after, and you only get there through data-driven experimentation and iteration, not a whiteboard exercise.”
Q: You've previously talked about AI accelerating a power struggle between CROs and CMOs. Can you share a bit more about what you’re observing?
Harrison Rose: “AI is influencing top of funnel faster than bottom of funnel right now, and the question of who owns that is getting much more complicated.
Even before AI, the debate was already there: should SDRs roll into marketing or sales? AI is that problem times ten. If I give either a CRO or a CMO $50k and tell them to go drive as much pipeline as possible, through email, ads, AI, SDRs, events, whatever they want, who owns that? The CMO or the CRO?
I think the people who are going to be most successful are those who are the best at interpreting data and using it to go to market effectively with a combination of humans and AI. But the convergence of the CRO and CMO roles, particularly at the top of the funnel, is going to be a genuinely fascinating and uncomfortable thing to watch play out. CROs are meant to own revenue end to end, but how willing and capable are they to really focus on what’s required at the very top of that funnel? I think it’s one of the more underrated tensions in GTM right now.”
Q: What's the biggest misconception founders and GTM leaders have about AI's role in the revenue function?
Harrison Rose: “That it can do more of the work in establishing product-market fit and go-to-market fit than it’s actually able to. We’ve seen companies get mis-sold on this, with AI SDR pitches that promised to just go and find pipeline and close business, selling themselves as a silver bullet to immediately find GTM fit.
AI can be genuinely useful at very specific points in that process, but you still need to understand who your customers are, identify their common pain points, build a solution for them and work out how to communicate the value. AI can help you draw insight from conversations, but you still need to go and have those conversations. And AI is only as good as the size of the dataset you’re feeding it.
My honest advice for early-stage founders is: AI isn’t going to work out your go-to-market fit for you. You still have to go do the work.”
