What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

**Brett Berson** (0:05)
When you go and look at many people with your backgrounds, the pattern is you worked at a massive at scale business, then on a relative basis, you join a startup as an executive, and a lot of times, it does not go well. And that person often goes back to operating at some massive scale after some stint.
And it feels like after a decade of doing real at scale building, you went to something very small and have had a really prosperous last four plus years. Why do you think you've been able to adapt and really do well in a very different environment where it feels like the default is like it doesn't go particularly well?

**Lindsey Scrase** (0:48)
Yeah. I mean, it often doesn't go well. You're right. I think that there's a few dimensions to this for me. I think there's like me as a person, and then there's the experience I've had, and then Checkr and what Checkr needed versus what I was bringing. I think me as a person, I have always really enjoyed going into completely new contexts and understanding first principles, but even just being an expat in a different country, immersing myself in a new experience. What are different ways of doing things and really learning from that versus taking my point of view and wasting it on where I'm going.
I've always liked that and been excited about it. At Google, I joined Google Cloud when we were a few hundred people in the go-to-market side, a few hundred million in revenue and so not dissimilar to the size and scale that Checkr is. People think Google had a ton of resources. Obviously, we do, unlimited funding in some ways for the startup that was Google Cloud, but it was very hands-on, scrappy, building and scaling with very little resources and scale. So we had no enablement, like pretty much seven of the 10 years I was there for any of my functions. We had very little rev ops or sales ops or systems folks or anything like that. So it was really building and figuring out how to do that at scale. So when you take that to the Checkr context, we had a lot more built out frankly at Checkr when I joined than I had at this similar stage at Google.
So there was that. And then I think that what Daniel was looking for, I joined as CRO and he had had several CROs before then.

**Brett Berson** (2:25)
There's no scarier job than being the first CRO at a startup.

**Lindsey Scrase** (2:27)
It is a terrifying job.
First to blame when numbers aren't hit, which is hard. Because is it the person or is it the product market? Exactly. It's very difficult.

**Brett Berson** (2:36)
It depends on who you ask. If you ask the CRO, it's the product. If you ask the CEO, it's the CRO.

**Lindsey Scrase** (2:41)
I think that where Daniel, what he was looking for at the time when he was hiring me, was someone who could be incredibly data driven, who was very operational. We were, at that point, had been very successful with gig companies, selling verifications, background checks, and we're looking to, we kind of dabbled in enterprise, we could summon mid-market, starting an SMB, and really wanted someone to think multi-segment, operationally data-driven, high-velocity sales, layering on top. And so that was something where I knew, like, what he was wanting to buy, I was selling, there was like a really strong product-market fit, so to speak, from what I was able to bring. And we really vetted that throughout the interview process. I didn't want to go somewhere where they had, you know, illusions of what I was going to do, or what I was going to be and I wasn't, and there was a really strong fit there.

**Brett Berson** (3:32)
What do you think is unique about building a business like that, where there's already a category leader, and you're trying to gain market share, versus a business where maybe it's a new market and you start out as the leader, or it depends on maybe how you look at the Checkr market, but maybe when you joined, it felt like in their sub part of the market, they were the category leader. What are your reflections on business strategy, order of operations when you're trying to go after a market with a clear leader already?

**Lindsey Scrase** (4:01)
I think it requires a lot of humility to understand, like, where are you gapped versus an incumbent? With Google, we were going up against Microsoft or an Amazon, and Google is a category leader in other aspects. And so I think at first, there wasn't the right understanding of the investment we need to make in marketing, and the investment we need to make in product go to market. Like, hey, we'll just do this. And at Checkr, I'd say it's been similar over the years, where we early lead in all of the gig economy, high-volume hiring, and then shifted to enterprise. And again, like, this was six-plus years ago, but had some failures. We thought, like, hey, we can just do this. Enterprise is the same, and it's absolutely not. And you have to think about it in terms of focus, I would say, is very important. You can't go from being a challenger in the market to capturing everything overnight, but really thinking about where is that focused vertical or verticals where, you know, you can win. And so whether it's at Google Cloud, like innovative companies or, you know, high volume, like or high growth startups is where we really leaned in, but those will become the big companies. And they were going immediately to Cloud, not kind of shifting from on-prem to Cloud. So that was a big part of the strategy.