A Product Market Fit Show | Startup Podcast for Founders
00:27:37 · Pablo Srugo, Alex Halliday
[00:27:37] S1: Give me a sense of just that growth curve. How fast did you get to a million? How fast did you get to, five or ten or whatever? [00:27:42] S0: We got to 1 million in Q1 of 2024, and then we hit ten in 2025. That was kind of a big ramp for us. We actually hit thirteen in Q4 of 2025. So that just was like an insane year for us. It was the machine starting to work, right? It was the positioning getting better, as I mentioned, and just it really clicking with the market with the tailwind of AI and people being concerned about ChatGPT, and shifts there. But then also internally, really learning how to have a repeatable motion. Which something that my co-founder actually has really been leading, but it has been a masterclass to me in iterating on process and just continuously practicing, and tweaking as we learn more and more. And the sort of sophistication of that just building over time. [00:28:29] S1: Yeah, let’s go deep on that. I’m thinking in my head, I’ve got this portfolio company I work with closely. We’re at $2 million ARR, things are clicking, product market fit is there. We’re trying to get to that 10 number, and things are just working but it’s a little bit still happenstance. Still a little too messy, not predictable. What did you do that really worked? What is that setup that you ultimately ended up with that helped you grow from one to thirteen and whatever that is, eighteen months or so?
00:28:55 · Alex Halliday
[00:28:55] S0: Yeah, we had two sellers in initially, right? So we had two AEs that really taught us a lot as founders about communicating the process and really iterating that kind of default playbook. Because you can do jazz as a founder in a way that you can't do when you have real sellers in. So first two in, there's some competition between them, right? So that's good. You don't want just one because you have no point of reference and what we quickly learned through those two is that people really liked how we were showing up, like the personality of our sellers and how it was a consultative sale, right? Because AI is scary, people are anxious, people don't know what to tell their board, the boss. It's a time of a lot of emotion, actually and so we learned very early, that showing up and being disarming, helpful, knowledgeable, and prepared really worked. So the first thing was like, can we make these two sellers successful? Turned out they absolutely crushed it. But interestingly, in very different ways, they had very different styles initially and then the next thing was finding our sales leader. And that's a hard one, right? Because as with any exec right now, you don't want people to over rotate on a playbook that's like kind of out of date because things have just shifted. But you also don't want people to have no frame of reference or sense of what good looks like. So you're actually trying to thread the needle where they know a lot and they're also prepared to throw it away should they need to. And we found this sales leader called Nick Casale who just felt it was a little bit more of a step up higher than some of the other people we talked to who are seasoned SaaS veterans. They've fucking seen it and done it. Sorry, sorry and my co-founder and I met with Nick and he was just, first of all, incredibly charming and had done his homework and prepared. And I think following the line of people, buying from people, they really, at this moment, want to feel a sense of security and safety. I think, particularly from their vendors, weirdly. We felt like he was the right fit and he was able to then bring in a lot of, people from his network and start layering on.
00:30:55 · Alex Halliday, Pablo Srugo
But the amount of iteration you have to do on this process is wild, like across every dimension from first call deck to how you do discovery to the AI processes you have in the background for processing sales calls. [00:31:07] S1: What were some of the biggest findings? I don't know if most of your leads are outbound or inbound. I don't know what your process is, if you have a demo or if there's PLG. What were some of the biggest things that you're like, holy shit, that really worked? [00:31:19] S0: Two things, deep discovery at the beginning and I'm a founder who wants to talk about product but I've really learned to shut up and ask questions. Then showing up really prepared. There's a specific channel we focus on. It's organic growth. There is publicly available data on that. We understand how they're doing. We understand how their competitors are doing. We can talk to that confidently. [00:31:37] S1: And this is enterprise sales, by the way? What's the ACVs just for context? [00:31:41] S0: Enterprise sales. The ACVs are sixty to two hundred and fifty, right? It's a big range. [00:31:46] S1: OK, so meaningful. Not massive, massive, but meaningful enough it's worth spending the time.
00:31:46 · Pablo Srugo, Alex Halliday
[00:31:46] S1: OK, so meaningful. Not massive, massive, but meaningful enough it's worth spending the time. [00:31:49] S0: Right, and so we really got very good at all of the automations of background processes and things to make our team fully prepared, right? To step into that call and not to firehose them with information. First to listen, really good discovery and then to start to talk to them about their priorities, but in the context of their priorities, have the data to have a meaningful conversation. And for some sales reps, that's quite different, right? Because they're used to saying, we sell email marketing software and it works like this. But actually, we need to earn the right to be part of their stack at this moment. Because competition is so high and we earn that right through the software. But also through the feeling that they have when they leave a call with us, and really giving them the feeling that they want to bet on us for a three to five year period as things change just immeasurably. So I really just have a lot of respect for how my co-founders run this and worked with the team to just create a culture of, experimentation and just making sure we learn with every call. [00:32:48] S1: For the higher end of that, the ones that are let's say $100k plus, right? Are you doing pilots? Are you doing some sort of trial period? Are you just signing them up annually? What works?
00:32:57 · Alex Halliday
[00:32:57] S0: You have to do pilots at the beginning. You have to be prepared to prove your value. We actually, last year, I think we had all but two pilots convert to annual. Which in the world of AI is actually insane and it's because it takes us four to five weeks to onboard a customer. Because we take them through a really rigorous process that we've actually built out of necessity. I'll give you one tiny sliver of that, is getting a customer to agree on their brand voice. So that they can actually use our systems and people think they know, but they don't know until you start showing them things. So calibrating with customers, that onboarding process, us holding their hand through that flow and making sure that they get to great as part of that POC is how we build a lot of trust in us. So we do POCs sometimes, less and less honestly, because there's a lot of proof points in the market. We typically start with two really strong focus areas that we want to work with them on. Because there's a million things we could do and then we have a roadmap of things we want to get to. And then one thing we've invested in from the beginning is education. So we offer to put all our customers through a training cohort where it's super fun. They become a content engineer at the end. A lot of people update their LinkedIn job titles. We throw conferences around that. So education-led sales and a consultative-led sales has been a big part of how we have gone and done this.
00:34:17 · Pablo Srugo, Alex Halliday
[00:34:17] S1: Here's a pointed question about the sales leader you mentioned. Out of these four things, what do you think is the most important for a sales leader. The ability to manage people, the ability to hire and recruit, the ability to implement a process, or the ability to sell themselves? [00:34:30] S0: I think it's hire and recruit followed by manage. It's an energy-led sport. The team has to want to win with you at the helm as a sales leader and I think Nick does that exceptionally. He's just the best in the world I've ever seen and it's incredible to watch. [00:34:45] S1: That's been, for what it's worth, my number one kind of observation for any leader across the organization is, are they able to hire and recruit? More than anything else, do the people that are going to be in that department want to work for that person? In some cases, it means maybe they also need to know how to build, or they also need to know how to sell, or they also need to know how to market, because that builds credibility. But that's a means to an end, where the end is, are you able to attract and retain the absolute best people? And if so, you're a leader. And if not, at best you're an IC. You know, everything else is secondary to that. Just because once you're scaling, I know there's all this AI stuff and for sure that's changing things, but you still need great people. You continue to need great people and great people want to work for great people. So if you've got that flywheel going across every department, everything just gets so much easier.