A Product Market Fit Show | Startup Podcast for Founders
00:30:18 · Pablo Srugo, Nick Fleisher
[00:30:18] S1: Is that when you hired an AE? [00:30:20] S0: I hired an AE before that. We hired our AE like end of the summer, like September, August. Basically, as soon as we raised our pre-seed, I hired an engineer and a completely counterintuitive to what investors told us. And I think most were like, why the hell are you hiring a salesperson when you arguably don't have PMF yet, right? Like you have signs of it, but like you arguably don't. And my justification is like he was a product market fit finder. Like that was his job. It was not to go hit some crazy quota. It was to literally go take what we're learning from the five design partners and go demo with a hundred clients a week, like go crazy and just see if what we're doing actually resonates with them. Like, would they all go adopt this? Right. That was like us prepping for the storm of like, are we doing something that's actually scalable or like that five companies happen to have a problem or like have as their own pain points? [00:31:07] S1: This is like the first kind of we want to go deep on this tackle because this is like you said, it's very unconventional. Even me, like the number one thing I'll tell founders is go sell your first million yourself. Like is that product market fit finder job not supposed to be yours? Like why would you outsource that?
00:31:07 · Pablo Srugo, Nick Fleisher
[00:31:07] S1: This is like the first kind of we want to go deep on this tackle because this is like you said, it's very unconventional. Even me, like the number one thing I'll tell founders is go sell your first million yourself. Like is that product market fit finder job not supposed to be yours? Like why would you outsource that? [00:31:21] S0: I would say we were doing it as well. This was a situation where there was someone who was so exceptional in the market. He was the top sales rep the last two years in legal tech. Like he sold $10 million each year at a legacy contract management tool with a terrible product. He knew everyone in the market. I knew him through going to conferences and I saw him sell into McKinsey and get a meeting with the chief legal officer when even I couldn't get a meeting with the chief legal officer. And so it was just like one of those moments where I wouldn't have hired any other AE. It was someone that made so much sense for the market and for where we were that like I couldn't afford not hiring him. Right. Like sure. Maybe you could have argued I should have waited six or four months, but like the risk that he would not be on the market just wasn't worth it for me. [00:32:03] S1: Okay. So it was more of a person driven thing. [00:32:05] S0: It was definitely person driven, but I think what it ended up becoming was like actually very helpful. And like I still did all the sales calls. I still closed all of our deals. Right. But he was just more firepower to be able to do that at more scale.
00:32:05 · Nick Fleisher, Pablo Srugo
[00:32:05] S0: It was definitely person driven, but I think what it ended up becoming was like actually very helpful. And like I still did all the sales calls. I still closed all of our deals. Right. But he was just more firepower to be able to do that at more scale. [00:32:18] S1: Did you guys do the deals together then? How did you how did you split things? Like where did he come in? Where did you come in? [00:32:21] S0: Most of our deals we did together. He did a lot of top of funnel and discovery and getting the initial calls. He he has a big following in the market. He would host these like wine dinners and coffee events with general councils. And so he was very good at like drumming up interest and building community. And then he would then bring myself and Jared in as we started to go further into the deals. [00:32:41] S1: And was that like his ability to bring top of funnel was because he was already in the space selling like I assume he brought in a lot of previous customers at top of funnel. [00:32:48] S0: I think that's one piece of it. The other is just he's an unbelievably personable person. Like he is so good at building relationships. One of our first clients that he signed was it was ridiculous. The first week he joined, he signed a five year deal with a client like paid five year deal off the bat over lunch. And we were like the whole office was like, what what just happened? [00:33:10] S1: I need to interview him. And how do you how do you do that? That's crazy.
00:33:10 · Pablo Srugo, Nick Fleisher
[00:33:10] S1: I need to interview him. And how do you how do you do that? That's crazy. [00:33:13] S0: You should. But this GC at this company said to him like, hey, I, you know, I just want to make sure like I'm getting the best service here. Like, how should I trust you guys? And Oliver said to him, like, you can call me whenever you want. Like, I will pick up the phone at any moment. Like, that's how you know that you're getting the best tool and the best team here. And the guy did end up calling him in the middle of the night, like literally at like two, three. And Oliver like doesn't sleep. Like he it's not because he he works so much like he actually just like can't sleep a lot. [00:33:40] S1: What could be happening at 2 a.m. that he needs like this like a test or something?
00:33:44 · Nick Fleisher
[00:33:44] S0: No, it was a test. It was a test. And Oliver picks up the phone. He's like, hey, what can I help you with? It's stuff like that where it's like building those relationships. And some of the like our fortune 500 deals take months and months to close. Like we have deals closing now. And like we've had deals closing over the last four or five months that like Oliver and I started incubating at the end of last year. And that's like people are saying tell us like how do you get how are you able to get such big deals? And part of it is just because we've been working on it for a while. Like we've been building relationships there. Like some of the fortune 500 clients we have. We've like multi-threaded with 50 stakeholders over the last nine months, the two of us. And he's flown to these places like over and over. And so like founders need to be selling, right? Most of my day is demoing and selling. But I think it's just allowed us to move a lot faster. Like when we launched and came out of stealth, we had a ridiculous, we had like 10 to $15 million of pipeline like already ready to go. Like that we had been warming and demoing. We had done hundreds of demos already. That's because Oliver was just an extension of us and he also knew the market and had all the right traits. It then sets you up for a very good sales culture going forward, right? Like we know the things that work and the things that don't. We've tested all the tactics. So like when you start to get into like the real growth curve, like you're not testing the waters and trying things out all over again. The other thing I'll say is like his role early on was very tied to product and engineering. Like he would do these demos. Liam, Jared, and I, the co-founders, we were all coding. And so us plus the early engineers we hired would just like listen to Oliver do these calls. We'd hear someone say something that was wrong or didn't look right. And we would just go start working on it. We had one little room in the office that was like had a door that was not really closeable so it wasn't silent. And so we would just hear him do these demos and we would just start working on it right away.
00:35:28 · Pablo Srugo
[00:35:28] S1: One of the maybe classic pieces of advice tied to this is one of the reasons you don't hire an AE so early is because an excellent AE wants a product that's already got that traction that they can come in and be like, yeah, I'm going to hit quota. I'm going to destroy quota. Like if you're already selling this much, I can sell that much more. How do you get somebody like Oliver to join this early on?