A Product Market Fit Show | Startup Podcast for Founders
00:28:02 · Nick Fleisher
[00:28:02] S0: Yeah. One of the biggest ones for us was we built these teams and Slack bots early on where you could drop the bot into a channel and it would triage and help manage and answer legal questions. And then it would pass it on to the right lawyer person to work on. And we were like, these legal teams told us they were working on this much stuff, but we're only seeing like this much come through Slack. And so we're sitting there watching these folks do their workflows on their computers. And we're realizing like their Slack DMs and their team's DMs, like their one-on-one messages are actually like so many unreads, like way more intense than any of the channels. And we realized like it was just a common behavior in some of these companies where like people would go to the lawyer that they knew best. And so that's when we like really invested in like building out the intake and triage capability from private DMs rather than just group channels, just because we saw people doing that. I think the second one is like most of our integrations have been through like us watching how people jump around different systems. So like it's obvious to say we need a Salesforce integration because everyone does the CRM integration. But like our biggest integrations today are actually procurement tools like Coupa and Zip. And we discovered that because we're sitting there watching someone drag an agreement out of Coupa, download it, drop it into Sandstone, then use Sandstone to work on it, and then drop it back into Coupa, right? And then we said, okay, like that's something we're going to automate. We sat there, we worked with them to figure out how to automate it through Coupa. And now that integration is powering like tens of thousands of contracts or agreements a month. A lot of times the clients or customers just don't, they don't know the art of the possible yet. I mean, so you have to kind of watch their current state workflow actually happen. Like even when we're doing remote sales and post sales, we make clients screen share, right? Like it's the most powerful thing just because you learn so much more than doing it on your own or like, you know, running it through a mock instance.
00:29:49 · Pablo Srugo, Nick Fleisher
[00:29:49] S1: When do you actually start, like you do these design partnerships, when do you start selling and go to market? [00:29:54] S0: We raised and we quit in July, August. We had all these design partners. We started to like really do real sales towards the end of the year. Like we wanted to see the design partners convert to feel like we had real product market fit. That's the same time where we saw that design partner go introduce us to a bunch of different accounts and say, hey, you need to work with this. That's like the end of 25. And then into 26, like we started to build a real pipeline and sell. [00:30:18] S1: Is that when you hired an AE?
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?