Why future COOs need sales experience | Lindsey Scrase (COO, Checkr)

Brett Berson 0:00 [upbeat music] When you go and

Brett Berson 0:06 look at many people with your backgrounds, the pattern is you worked at sort of 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.

Lindsey Scrase 0:26 Yeah.

Brett Berson 0:26 And, and it, it feels like after a decade of doing, you know, real at-scale building, you went to something very small and have had a really prosperous sort of last four-plus years. Why do you think you've kind of been able to adapt and, 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, and 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, um, and then Checkr and, like, what Checkr needed versus what I was bringing. Um, I think me as a person, I have always really enjoyed going into completely new contexts and understanding, like, first principles, but even just, like, being an expat in a different country, immersing myself in a new experience. Like, what are different ways of doing things? And, and really learning from that versus taking my point of view and, and foisting it on, you know, where I'm going. So I've, I've always liked that and been excited about it. Um, at Google, I joined Google Cloud when we were a few hundred people on the go-to-market side, you know, a few hundred million in revenue, and so not dissimilar to the size and scale that Checkr is. People think, you know, Google had a ton of resources. Obviously, we do, like, unlimited funding in some ways for, like, the startup that was Google Cloud, but it was very hands-on, scrappy, building and scaling with, with very little resources and, and scale. And so, you know, we had no enablement, like, pretty much seven of the 10 years I was there for, for any of my functions. We had, like, very little, like, rev ops or sales ops or systems folks or anything like that, so it was really building and, and, and figuring out how to do that at scale. So when you kinda take that to the Checkr context, we had a lot more built out, frankly, at Checkr when I joined than, than I had at the similar stage at Google. So there was that, and then I think that

Lindsey Scrase 2:18 what, what Daniel was looking for, I joined as CRO, and he had, 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, it's a terrifying job.

Brett Berson 2:29 [laughs]

Lindsey Scrase 2:29 Uh, first to blame when numbers aren't hit, which is hard-

Brett Berson 2:32 It's funny how that works

Lindsey Scrase 2:32 ... because is it, is it the person, or is it the product market fit?

Brett Berson 2:34 Exactly.

Lindsey Scrase 2:34 It's, it's very, it's very difficult.

Brett Berson 2:36 It depends on who you ask. If you ask the CRO, it's the pr- 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, at that point had been very successful in, with gig companies, selling cert- verifications, background checks, and were looking to... We'd, we'd kind of dabbled in enterprise. We could summon mid-market, starting in 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, 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 wanna go somewhere where they had, you know, illusions of what I was gonna do or what I was gonna be, and I wasn't, and there was a really strong fit there.

Brett Berson 3:32 What do you think

Brett Berson 3:33 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're, 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 subpart of the market they were the category leader. What are your, like, reflections on, like, 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, where are you gapped versus, you know, an, an incumbent. With Google, we were going up against a Microsoft or, or an Amazon, and Google's a, a category leader in other aspects. And so I think at first there wasn't the right understanding of, like, the investment we need to make in marketing and the investment we need to make in, in product go-to-market. Like, "Hey, we'll, we'll, we'll just do this." And, um, at Checkr, I'd say it's, it's been similar over the years where we, like, early lead and, you know, 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 where [laughs] thought like, "Hey, we can just do this. Enterprise is the same," and it's absolutely not. And you have to think about it, um, in terms of focus, I would say is, 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, s- high volume, like, or high growth startups is where we, we really leaned in. Th- 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, a big part of the strategy. At Checkr, it's where we know we're huge value add versus, like, entrenched incumbents, so people like, industries like staffing, gig, retail, hospitality, manufacturing were doing a lot of hiring, and they need the benefits of our technology and, and accuracy and scale. Um, so that focus is really important. And then the other thing is the, the company, the whole company has to be behind it. I've kinda said this multiple times, but I can't reinforce it enough. At Checkr a few years ago, we said, "Let's go into enterprise again." We're, we're evaluating the strategic decision, uh, 'cause it's an investment of resources and, and really our, our R&D team's time. And we had to, like, like, literally, like, shake hands around the table that You know, in engineering, in product, in legal, in people, um, obviously all of go-to-market, we are investing across the board. This isn't just something you can pilot. And then there needs to be that, like, really tight learning loop is probably the, the other most important thing, where, um, we have our, our chief product officer is meeting with customers daily. W- our product managers are on the calls with our customers daily with us to really get that very fast cycle and loop of, of feedback to know we're, we're still building and, you know, if, if you're a challenger, you have to be able to be agile and, and you can't just assume you have the right product and there, there's a lot of needs that enterprises have. So it's, it's a huge undertaking, and one that, you know, Google Cloud has been obviously very successful at. Checkr is-- we're like seeing-- we're seeing a lot of success as well over the, in, in our most recent few years here, um, and a lot

Lindsey Scrase 6:58 more to come.

Brett Berson 6:59 This topic that comes up with so many scale-up startups, which is, you generally build the business on the back of venture-backed tech or mid-market buyers, and then at some point, everyone realizes that, like, most revenue exists in the global Fortune 10,000, and so we're having all this success for this widget sold to this, uh, mid-market customer. We're just gonna take it to enterprise. You look at tons of companies that do that, it's so much more challenging to make that work. And a lot of companies have done it, but a lot of companies have almost blown themself up over trying to sort of e- dominating enterprise. Why is it actually much harder than some would imagine? You have this great product and this go-to-market that's working to sell it to, call it, 200-person companies, and now you're selling to 25,000-person companies.

Lindsey Scrase 7:50 I think that why is it hard, and there, there's so many things about why it's a challenge. I think that there's, obviously if you do the math, you're like, "Oh yeah, the deal sizes are very large. Like, it's a s- it's like a set list of accounts we go after. Like, no-brainer, let's go do this." They're not shifting providers all the time, so deal cyc- like, sal- deal cycles only come up every so many years, and they're often a year-plus-long sales cycle.

Brett Berson 8:15 And why, though?

Lindsey Scrase 8:16 The decision-making process at large companies is long. Um, there's shifting, often big decisions like this, like if you're gonna switch your cloud provider, if you're gonna switch your email provider, switch your background, your verifications platform, this takes a lot of internal resources as well from an engineering or, you know, development timelines perspective. So it has to align with the, the timing of their contracts. It has to align with their strategic priorities as a company, and if, if they're not, this isn't something they care about, it's not on the top 10 list, then you've got to figure out how to make it up there. And, and so even, like, that, that discovery with the customer to try to find and uncover pain and kind of paint that future vision is, is hard. The sales acumen is incredibly important. You're not order taking. You're not doing one or two pitches and closing a deal. You're engaging in a m- you know, a very complex sales cycle where you're building trust, you're multi-threading. Or if you're, like you're talking to the HR buyer, you've got to figure out, okay, well, who's the ultimate decider here? Is it the CH- the CHRO? Is it the CFO? Is it the CEO? You're doing, like, reconnaissance across the company to try to really get a good understanding. So there's a, there's a lot of challenges on the go-to-market itself, and you may be faced with, like, lack of brand awareness in enterprise, especially if you're coming from being a, you know, scale-up or startups know you only. Like, there could be billboards all over San Francisco, but your buyers are in, like, Dallas and Atlanta and Chicago, so it, it's a different audience. And then, like, I mentioned the, the product roadmap. Enterprise customers, there's always gonna be the last long tail of requests for, for any customer. They're rarely buying it off the shelf. There's gotta be something unique for their instance, and I mentioned, like in G Suite or Google Workspace, there is things we, you know, we thought product was complete and done, but there's a list of, you know, whether they're regulatory, um, or certifications that are needed for certain industries or just, like, bells and whistles, but they're really important to that customer. You have to build those. So that's the res- all the reasons why

Lindsey Scrase 10:23 it's very challenging. I think that what can make one successful in this is, I mean, multiple things, but one, on the product development side, it's really hard to differentiate what's a deal-blocker versus a nice-to-have or something that a customer wants versus something that they really need. And oftentimes, I think where people can go wrong is anything this customer asks for or prospect asks for, like, I'm gonna commit to building. So suddenly your, your product roadmap is, like, complete snowflakes for every single customer, which is not gonna work, and you're spread too thin. And on the flip side, or you're, you're, you're too arrogant and say, "Hey, we don't need to do any of this."

Brett Berson 11:05 And you can't close anything.

Lindsey Scrase 11:06 You can't close the deals, and then it's like product and sales pointing fingers, like where's the issue? The other part I, I mentioned is focus and, and making sure that, you know, I've seen enterprise sales leaders fail, where you're running sales teams, you're, you're kind of doing this in a repeatable fashion, but you're not getting hands-on into, you know, what specific accounts, why? How do we run targeted plays? You know, so for Checkr, for example, like giving the outbound motion, if you're going through enterprise, you have to get outbound pipeline generated. When I came in, it was not, not working. I'm like, "Okay, is this a strategy issue? Is it an execution issue?" Took like a year and a half to really uncover all the issues of why it wasn't working, and it was people, it was processes, it was the right strategy we were going with. And so I had to kind of tinker with it to find the right thing, but eventually figuring out and really getting laser-targeted into who are we focusing on? What events do we need to show up at? How do we think about- Getting their attention. Buyers are incredibly busy. You know, I, I get 100 emails a week from people trying to sell me something [laughs] . I don't read any of them. And so you really gotta get creative in figuring out, and especially in today's world of like AI slop outbound in terms of people's attention is more distracted than ever, how do you get their, um, get their focus? And so when you do really well in enterprise, you're able to focus on the right target accounts, figure out the right messaging and the right, like what's the pain they have and how do I address that and get, get ahold of them? And then, and then like running that sales cycle, you know, s- and being tenacious throughout, you know, what could be a year or year plus.

Brett Berson 12:47 So where do you think a company should start? You have a lot, let's say you have a lot of success, you're at a couple hundred million dollars in a mid-market business, and you wanna go build an enterprise business. How do you break that apart? Just in the way that you articulated, it's so multifaceted. It's, it can be so complex. Do you think there is a way to begin that's correct for most companies, or it's totally context dependent?

Lindsey Scrase 13:11 Translatable for any company, it's figuring out do we have the right people on the bus, so to speak. So hiring enterprise experienced sellers is, it's just, it's very different. Thinking about enterprise marketing is completely different than traditional growth marketing, um, and demand generation. So you need account-based marketing, you need, um, events, strategies, et cetera. Having the right product and engineering, um, investment to be able to do last mile needs and, and build for the enterprise specifically. So those are like table stakes. And then the how is to start in a focused approach. You can't spray and pray, and so often people will get like have a small pilot in a specific large enterprise and like, "Okay, we're, we're good. We're in the enterprise." Or a startup that they got when they were, you know, like let's say DoorDash was one of our first customers that was a startup when we, we started with them. They're, they're now obviously a large enterprise, but just 'cause you've scaled with that company doesn't make you enterprise ready. And so focusing on for traditional enterprises, where can you win? And even being as narrow as possible, like we closed, you know, a lot of car dealerships, very large, like Fortune 500 car dealership companies [laughs] . Like that's one where let's just keep taking them down, for an ex- as an example.

Brett Berson 14:33 How did you figure that out?

Lindsey Scrase 14:35 You need a really data-driven RevOps and, and sales team. We got like very, very granular using a lot of the tools out there, using AI, but just like, just people who are really focused and inquisitive. And then we started doing very quick iterations of like we're, we're starting to see good takedowns in a specific, we call them rich niches [laughs] . But then let's spin up more and more campaigns targeting that and, and like, you know, you have referenceable customers, you're seeing good takedown strategy.

Brett Berson 15:04 But, but do you think because of that that, again, let's say you're mainly a mid-market business. Should you be more in explore mode at the beginning, where you're more spray and p- pray, and you're trying to find these niches? Or you need to find a more efficient path to start to stack the niches on sort of top, on, on top of one another?

Lindsey Scrase 15:23 I would look at where are you performing well in the mid-market. Like do a really deep vertical analysis, talk to customers. Like know, like where are you acquiring customers really well? Where are they thriving? Your NRR is high, GRR is high. And then start there in a few areas. I wouldn't kinda go tackle the beast head on, 'cause it's a lot of money, and you wanna get the quick learning, and if you're spread too thin across too many verticals, that's just really hard. Unless you have a very completely horizontal product, but even with the buyers-

Brett Berson 15:57 But just elementally

Lindsey Scrase 15:57 ... it's different.

Brett Berson 15:58 Yeah.

Lindsey Scrase 15:58 Yeah.

Brett Berson 15:58 When you think about sorta getting this enterprise motion off the ground, should it be cleaved off, and you have a few sellers or marketers or whatever that you're kinda creating a new business? Or you actually want it very tightly coupled with the rest of the company when you're getting it off the ground?

Lindsey Scrase 16:15 I mean, the way that, um, I think things work best for anything like this, not just enterprise, is to have dedicated people trying and like moving quickly and sharing information together. I don't think it needs... So I wouldn't put it like totally embedded, let's put this through the exact same process for the rest of the company, but it, it shouldn't be like in a basement corner somewhere. When we started this, we had a small group of sellers. We had product manager. I said, I, I said, "If we're gonna do this, we need one dedicated product manager," 'cause there's not an enterprise, I mean, it's, it's like an entire product stack, but you need one person who is embedded with the team and is like the person and leader. And that was a hugely beneficial move because he was in the customer calls, he was coordinating with all the folks in engineering and, and product. That just helped us move and scale so much more quickly. So I think having some separation is helpful. And that could just be like specific name individuals, like in marketing, you're the person and product. They don't have to be completely separated.

Brett Berson 17:12 Did you find that you had to pre-commit to X number of roughly we're gonna spend a third of our engineering resources on what's coming from the, the go-to-market and product team that's with enterprise, or it was much more organic?

Lindsey Scrase 17:23 It was more organic. Um, and every, every quarter we're looking at that breakdown, and what we did align on is that there's gonna be an unanticipated work that we're gonna have to do, and we all need to align that, like we gotta figure out how to do that. Because even at the beginning of a quarter, you s- you set a, a roadmap, but there's stuff that's gonna come up from a new prospect where we gotta figure out how to fit it in, or an existing customer we, that we just ramped, um, because there's a lot of unknown unknowns at that point still.

Brett Berson 17:51 Do you think the, it's clear that the AEs need to understand enterprise and that being an enterprise AE is different than being an SMB AE or, you know, some version of a seller down market. Do you think the person leading revenue also needs To have enterprise experience, or you can have somebody that's much more in a transactional mid-market be successful at building out enterprise?

Lindsey Scrase 18:18 I mean, you always could have someone be successful. I come from SMB mid-market, so I was not the deep enterprise expert when I came to Checkr, and at that point, we weren't going big in enterprise.

Lindsey Scrase 18:30 So for me, it was really important to hire a sales leader who had done this multiple times, and had done it in an environment that was gritty and challenging, not where, hey, they're the market leader running an enterprise org. And that, like, that's valuable at some point, but no, "Hey, I need to go figure out what accounts to go after, how to take these down." And, and so that, I think is, is very important. Um, and then on the sales reps, we've got a, a great, like, um, internal mobility program where you can grow from being an SMB commercially up into enterprise. But what's very hard to train if they don't have it already is, like, that outbound demand generation hunger. So if you're taking and hiring someone, even in enterprise, but who's just had leads passed to them, they're in a market-leading position, or they're not having to do that, like, we were like, "That, that's, that's a no-go for us moving forward." So everyone needs to know, like, grown up through you work-- you make your own pipeline, which is hard to teach that if you've not, like, grinded it out on, on the phones or doing outbound without, like, a fresh, warm book.

Brett Berson 19:32 One of the things you mentioned briefly that's always fascinating to me is basically forever in go-to-market events tend to be very useful, and it takes in every possible flavor of taking people to VIP thing at F1, through cocktail hours, dinners, educational. And it feels very odd that still in 2026 that that's very effective, and it's generally very high ROI. Wh-what's going on with, like, events and selling products and why they tend to work very well, regardless of the, uh, the who the buyer is, or you could go through, and it just tends to work well?

Lindsey Scrase 20:07 Yeah. I mean, I also, you know, especially post-COVID, like, events were, were dead. We stopped doing anything, and then we, we piloted it and saw returns, watched it closely, and over the years have invested in-- so substantially in this. I think that the, the crux of it is, like, a sale is a, it's a, a big-- it's a leap of trust, and especially at that enterprise level, you're making a big decision. Often you're, as a buyer, your, your career, this is a big strategic thing you're, you're recommending internally. You don't wanna, you know, take risks on behalf of the company. And so a lot of that comes down to, like, the trust you're making in the individuals. Like, humans are humans. [chuckles] I don't think anytime soon, espe- like, in enterprise sales specifically, that's gonna be replaced, like, on, you know, like, the AI or on the agentic side. But, um, it's that human-to-human contact is, is kinda the biggest fundamental pillar. And then I think also, and where we try to focus our events is giving people something that they wouldn't get otherwise. So, like, I, I'm sure you get invited to events. I get invited to a lot of events. Most of them, you know, I've got children at home. Like, there's opportunity cost of going to an event if, like, I could work on my own work or be with my family is very, very high. And so it's creating enough interesting, compelling events, whether that's experiences they wouldn't have otherwise, like, not just another basketball game. It could be that, but, like, we've done, like, let's-- like, Houston Rodeo or Devil Wears Prada premiere in, in New York. Just something that's different, um, or, like, very strong thought leadership that's gonna help you in your job. And so it can't just be like, go to the same event. It's gotta be targeted and, and high value. And then lastly, like, at a lot of these events, they're meeting their peer set, which is for any leader, I always tell my leaders, that's an important part of your job, is to break from the day-to-day to get external context. And for most of these, they're with a bunch of other folks outside and, and that's hugely valuable for them. So events are not dead. It's, it's-- and I don't think they're dying anytime soon.

Brett Berson 22:05 If you think about going from CRO to COO

Brett Berson 22:08 in the context of Checkr, what was by far the hardest parts of that?

Lindsey Scrase 22:13 The mental shift, especially in a large company like Google, even though we were s- Google Cloud, smaller when I joined, but you're, you're managing your own functions, and you're, you're working to push cross-functional teams. That is your direct area of accountability. And so it was, I think, a few things. One was inserting myselves into other people's business who were not on my team. So, like, let's look at the supply chain, you know, which was owned by another function at that time. Like, how can we improve that? Or our recruiting velocity and our hiring approach. Like, is this working well? "Hey, let me partner with you on that." Looking at our metrics, like I, uh, from-- with, with our CFO at the time, like, "Hey, I, I don't think we're necessarily measuring all the right metrics. Let's look at adding some other ones that better define the business." So that was, uh, an adjustment, especially like, no, those people don't-- those are my peers objectively.

Brett Berson 23:03 Right.

Lindsey Scrase 23:03 But I had to, to lean in, you know, and, and push them. And then also working with Daniel. He-- we spent a lot of time intentionally on a few things, but one is continuing to build trust, um, continuing to give him feedback, and he wants to be pushed as well. Give f- like, feedback both ways, obviously. And then figuring out the right balance of, hey, running the, the, like I do our, our company business reviews and, you know, and he's sat back more. But making sure that he's, he's a founder. He, he cares deeply. This is his baby, and, and making sure that he's aware of everything he wants to be aware of, even though he's not in the day-to-day. So that's-- and, and he and I are always working through that and, and finding the right balance to make sure we're on the same page.

Brett Berson 23:49 What did you figure out about how you go about solving these problems that sit outside of the part of the org that you're directly responsible for? Like, one would imagine, "Why are you involved in what I'm doing here?" Like, very easy to get defensive, very easy to get territorial, very easy for you to, like, for that person to then say, "Well, what, what-" Let's talk about your part of the, you know, or like all the interpersonal things

Lindsey Scrase 24:15 I think it, it starts with trust and, and building that trust with each other. I think we... One thing I've also done at the company is build out ... I'm a big believer in cadences and connection, so all of the cadences with our s- C-staff. It's, it's six of us including the CEO. But when, you know, we do off-sites together and like ways to connect on a deeper level so that we can have difficult conversations. Same with our VP level, our director level, all of that I, I coordinate. But, um, so that's a big part of it, where you can, you have the license to push each other. Um, I think the second is that I had to get out of my own way and like this is my job. I debate, I push, but I like harmony and, you know, I, I, I had to tell people explicitly what I was doing. Like, "Hey, this is, my job as COO. I'm, you know, I wanna partner with you. Like, this is, we're like a lot ... We're, we're working on this together. I don't have the right answers always." And, and I get a lot of benefit when they push me. Like, "Hey, you're..." Our, our chief product officer when he came was like, "You're, the sales collateral's not very good." [laughs] He's like a, a very strong enterprise focus product leader and, you know, "You're right. Let's like go improve this together." So there's some, there's, you know, it, it should go both ways. I think that the, from a mental framing as an executive in this role, it's that this is what is expected of me, and it's, we're not doing well if like go-to-market's functioning well or operations is functioning well, but there's issue over, issues over here

Brett Berson 25:43 This builds on what you were saying a second ago about, you know, building cadence and, um, systems and processes you scale. And it feels like if, if it's not done well, you end up in corporate bureaucracy land and people spending more time filling out OKRs than they do like doing the work. You kind of, it feels like have this fundamental tension where you're trying to figure out how do we have as little work around the actual work that people wanna do. But I think you get to, it's almost like a law of physics. You get to a certain size company, and it might be 30 to 50% of the time if you audit what someone's doing, it's not doing actual work to make the product better, deliver for a customer, on and on. And so like what's your general philosophy on the role of process and standardization while also sort of allowing for judgment, agility, pushing decisions to the edges of the company, sort of the tension in sort of those two things?

Lindsey Scrase 26:41 Yeah. I mean, decision making is one we've been actively working through right now, and that's, it's a very hard one. 'Cause that drives a lot of ... Like, the more process you have to kind of take things up the chain, so to speak, the more people are spending on internal stuff versus, um, getting work done. We, especially in a founder-led company, the reason the company took off so well is that you've got incredibly bright founders who make a lot of decisions. And d- I think at Checkr kind of have got into a routine of a lot of decisions just naturally flowing up. If you give an executive a decision, they will make the decision. Um, and so we've worked to try to, you know, turn that in an intentional way, um, and just, I mean, like very practical things. But like first of all, Daniel and I sat down a couple years ago and said, "Okay, what, what are the decisions that you need to make? Let's like just document it."

Brett Berson 27:32 So what are some examples of that?

Lindsey Scrase 27:34 Like deals above a certain size or any major brand campaign. Not like a demand gen, but like any major brand decision. Any, um, product monetization that's going like in a completely ... Like, we're a consumptive model. Uh, like changing a product to SaaS is an example. Our CEO cares about swag, so it's like what we put out there and people are wearing. Like that's like, that's like an exception he gets. That's not, you know, a big one. And we keep looking at it and saying like, "Where can we push that down to,

Lindsey Scrase 28:03 you know, the next layer or the next layer?" So there's that. Um, we've also, like I tend to think there's like the whole like rapid recy- I, I think sometimes it's just like too much process. But what we've rolled out is two things. Um, one for every initiative or anything happening, like who's the DRI, di- directly responsible individual? And that's just in our lexicon, um, because we s- we saw a lot of like swirl happening around like unsure who was taking the next step to own something. Codifying who is the decision maker, because we, we saw naturally everything was just flowing up and then, and it wasn't always obvious that certain executives were deciding everything or everything was flowing up to VPs. And so it forces us to s- say like, "Oh wow, this, I'm the decision maker on a lot of things." [laughs] Like push it down. Like as an executive, as a leader for, uh, how I think about my time is the ROI of my time on a decision should be high. So it, I should be able to do distinctly better than someone below me or, or deeper in the organization. And if I'm deciding things down there, then I'm not getting shareholder value. Um, and so that's like one big thing we put in place in terms of like mechanism to flow decisions.

Brett Berson 29:07 And so w- with that in your world, at this point in the company's life, what do you think the things that you should be DRI on? And maybe what are some things that other people might think you should be DRI on, but you sort of very strongly believe it should sit somewhere else in the org?

Lindsey Scrase 29:23 Key DRI, like what is our ... How are we thinking about like m- major product roadmap trade-offs? Like that's probably the thing we disagree and debate on the most as a company is there's so many massive opportunities ahead of us, uh, we could go run after and, and capture revenue very quickly. How do we sequence those? What do we not do? Um, so that's at the, at the exec level decision because it really should tie to our three-year roadmap and strategy. Um, I think an example of something where I maybe decide on but I push it down is like what, how many sales reps should we have in, going into next year? We're going through that decision right now. And I think that if you're aligning incentives of everyone, like people are getting paid on the things that are right by the company, if their goals are really thoughtfully aligned, then like a lot of those things are people Are gonna make the right decision. Big, like M&A is, is one where we're-- those are like, you know, one-way doors that we, you know, are hard. And then hiring is really important. So key, you know, any like VP level and above, those are... If you get that wrong, like that's gonna be obviously have a ripple effect on the whole company. You know, I have to do it, too. I'm a perfectionist. I am very data-driven and, um, and I always tell people, like, "Once I have your trust, like you, you go make the decisions." When I have a new hire, a new leader, I'm investing more time upfront. Like, "Here's how I would make a decision when, you know... Here's, you know, like, let's, let's like look at this one together, and then after the next one, like you go with it." So there's like coaching involved as well.

Brett Berson 30:57 What do you consistently find in terms of actual decisions are very challenging? Even if you have high-quality judgment and you have context on the organization, and it's in your remit that for whatever reason there's, it, it, it's oftentimes very hard to get it right.

Lindsey Scrase 31:17 I think hiring is one of the hardest things where, especially executive hiring, where people just are really good interviewers at that stage in their career, and the stakes are high in term. And so I've made bad calls there, um, either maybe over-indexing on someone who's got like a ton of-

Brett Berson 31:34 Relevant experience

Lindsey Scrase 31:35 ... relevant experience, um, or, or betting on someone who's not at that exec level, but has the intrinsics who couldn't turn the corner. In negotiations with very high stakes where there's not perfect information and there's no perfect decision. Um, and I think that what I've learned over the years is that you're, you could make a really good decision and still have a bad outcome, or you could make a really poor decision and have a good outcome. And how do you become good at the process of making decisions? Which for me, as a, as a, you know, recovering perfectionist, it's like you're gonna make the best decision you have with the information you have available, and you have to make a decision. Nothing worse than that is like no decision. I'm working on it then like with my team as well, like if you know how to... If I trust your process of making a decision, then like hopefully you'll be right, and nine times out of 10 you probably will, but there will be some misses and I might have m- had the same outcome.

Brett Berson 32:32 Do you find that even when you, when you build trust with somebody who's owning something in your org, that you still need to stay close, such that you can actually sort of have a feel for like the business? Or there's this risk that you turn into like a Dilbert exec that's like so separate from everything, and so you, you have to stay close to the metal?

Lindsey Scrase 32:55 Absolutely. And I think it's easier than ever now. Staying close to your team, but then like the, the broader organization. I-- even in our office, I have a, um... Daniel and I kind of sit together in, you know, one area, then I have a separate place. I just sit with the team, like in the sales floor or whatever, just to kinda hear through osmosis what's happening, talking to people in the hallway, et cetera. But now with AI, with-- We're heavy Slack users. We have a channel for every single customer, every single deal, you know, very structured about this. I, I can regularly keep pulse of everything. Getting that like felt sense of intuition and sentiment is what's important to me. Like I'm very data-driven, but an intuitive decision-maker, you know, layering the data into it. And so if you're not getting that, if you're not-- if you don't have a process by which to, to glean that, then you're often operating blind. I believe that the best way to make a decision is getting as close to the customer as possible, and often the people on the front lines have the answer. [chuckles] We're just like sitting over here, like pontificating and, and so to me, it's often like, let's bring the people who actually are close to this into the discussion, either directly or like let's make sure we're getting their input. I've seen this in, in both ways. I've, I've been like, you know, in an organization where people are making decisions with completely lacking context.

Brett Berson 34:13 I would think one of the things you, you spend some time working on in your role is like incentive design. I mean, maybe in the most extreme you-- there's so many important things as it, as it relates to running a go-to-market team and figuring out like things like comp. What are some of the things that you figured out as it relates to incentive design or like mistakes that you've had to correct or sort of things like that as you try to figure out how to incent and align many, many, many, many people?

Lindsey Scrase 34:42 I mean, the biggest, um, experience I've had in this and learnings has been in the like sales compensation, um, in moving from a S- SaaS model to consumptive. So at Google, we were in G Suite, a SaaS, like you book a deal, like you give rep credit, and you don't really have to do anything. It's incredible. And then whereas consumptive, you have to close the deal, they have to ramp, you have to predict how much they're gonna spend. And so I've lived through this transition twice now. When I came into Checkr, we, um, people were comped on bookings. So it's like how much the customer is gonna spend. How much do you think they're gonna spend? In reality, we don't collect revenue until based on like how many checks they're running. And so we, um, you know, people were getting way overpaid for things that maybe weren't going live or the actual revenue realization was very different than expected. So incentives were completely off. So we had to do a pretty dramatic change, and we're doing this with companies we acquire too, where you're comped on revenue. Um, and then therefore, I know like if you're, if you're comped on this, you're, you're aligning, you know, your pay is aligning with value to the customer, which is then aligning with revenue to Checkr. And we've had to like tweak some things here and there, like what's some sort of leading, leading thing we can give them when the deal is closed? But it's been a game changer in terms of the way like customer engagement, because we're doing what's right for them, and we're not just overselling them on something or overbooking things. And then making sure that they're going live and that rep is like very attuned to make sure that that all happens seamlessly. That's a big one. I think it all comes down to what are we trying to achieve as a company? What is this person uniquely positioned to influence? If you give them someone too much scope, then they're, they're not, they're not getting incented on anything. Like, if you're ... If I'm comping my sales leader on total revenue for the company, it's like that's, that's not, you know, high leverage for me. Um, and then, you know, just giving them the guardrails so that we, we don't go out, out of bounds. For a sales incentive comp, like, if you do all those things, and then you can set up to have a winning sales organization, then, then it's like these decisions are easy. Like, should we add more reps? Like, how do we, how do we treat this one deal? Like, it, it all ... It just makes everything easier than if you have, like, the shadow approach that's not aligned with your company's success. And oftentimes, like, for, for founders or for leaders, like, a, a sales leader will come in and say, like, "No, no, no, we need to do it this way," and like, "No, you don't." Really think first principles.

Brett Berson 37:12 What other reflections do you have about, uh, variable comp for sales? Because I feel like you have a bunch of, you know, founders that wanna think everything from first principles, and a lot of them begin with there shouldn't be variable comp for reps. And in the fullness of time, I think that basically every single one of them eventually gets to the point that says, "No, we should have variable comp. There should be sales commissions." [laughs] And I've always wondered why aren't more PMs on variable comp, and why aren't, pick any of these functions?

Lindsey Scrase 37:41 Yeah, I mean, I haven't thought deeply about the product or other, um, functions like engineers. I, I, but I, on the sales side, absolutely they should be on variable comp. And in by nature, you want people who are incredibly competitive, hungry, and who are gonna take this risk of 50% of their compensation is, is at risk. Like, sometimes I get asked like, "Why do salespeople make so much?" I'm like, "You wanna go take a quota [laughs] and have your salary cut in half? Like, have at it," right?

Brett Berson 38:11 I feel like that would be interesting. I, I feel like a PM should be able to say, "I'd like to be eligible for 40% more comp, but I'll cut my base by half." [laughs]

Lindsey Scrase 38:20 I think the hard thing there, which is, I think, love any thoughts you have, but measuring the effectiveness of the-

Brett Berson 38:26 Inputs and outputs

Lindsey Scrase 38:27 ... Yeah, is hard.

Brett Berson 38:28 Measurement.

Lindsey Scrase 38:28 And like, we, we talk about this all the time. Like, how do you know you have a high-functioning org? Is it the number of things they ship? Is it the quality? Is ... You know, there, the, it's, it's harder. I think the harder it is to have that scoreboard that you can look at objectively, um, the harder it is to put on a variable comp. But when you are very clear on, like, the input that's made, like, the output that they're driving, and that there's ... It's, like, a non-negotiable, very clear scorecard, it works well. There's, like, MBO plans where you're, um ... I've done those for certain roles where it's like, it's like five categories, and you're, you're rated on them at the end. It's just, like, a ton of overhead. It doesn't drive as much the same behavior. And, like, sales success breeds people staying, and enterprise AE is, is, like, a hot commodity. They can go other places. If they know they're gonna make a lot more money or be more successful somewhere else, they'll vote with their feet. And so you wanna have a, a good plan where there's a lot of upside. And that's another thing we've looked at is, like, I think you can get really stingy and be like, "Oh, this ... " We, like, you know, we have accelerators. If you're making above your quota, it's gonna go to accelerator, accelerator mode. We've had, have at times where, like, there's caps on that or we're s- we're stingy on that. It's like that's not the right move. [laughs] Like, to what, to what end? And if your unit economics are working, if you've done the math right, which, which you should be doing, then it all makes sense. Like, this, this math works. Shouldn't ... I think people, like, the, the, the highest performing AE should make a lot more than a lot of people in the company.

Brett Berson 39:59 It does feel like the fact that the, the work tends to be easier to measure makes it easier to comp in that way, which is that there's an unfortunate part of that, right? Because, like, a superstar theoretically, maybe the average PM should be comped at X, but maybe the superstar PM should make 3X or whatever, and it's ... And, and yeah, you have career ladders and this and that, but it d- doesn't work the same way as, as sellers.

Lindsey Scrase 40:23 I think, and then I think that's where things are moving more and more is, like, differentiating paying more for performance for across all roles, and especially with, um, you know, with, like, leveraging AI. Like, you can get, like, 10X more out of a certain amazing engineer than an average

Lindsey Scrase 40:39 one.

Brett Berson 40:39 In working across so many sellers, what's kinda your working theory if you take in any team that you've worked on and you look at the number one seller versus everyone else? Are they always doing something consistently different than ... Not what is difference between the, the best one and the worst, but the folks that are good and the person that's, like, the head and shoulder star on the team.

Lindsey Scrase 41:02 People, like, have the misconception about sellers. They're like, "Oh, it's the most, like, outgoing guy over there that's gonna be the best seller."

Brett Berson 41:08 A lot of them are very introverted, I find.

Lindsey Scrase 41:10 Yeah, yeah.

Brett Berson 41:10 But they have to turn it on.

Lindsey Scrase 41:11 Yeah, exactly.

Brett Berson 41:12 You know? And then to-

Lindsey Scrase 41:13 They can be, yeah

Brett Berson 41:13 ... re-energize.

Lindsey Scrase 41:14 It's probably t- two ingredients for me. I mean, like, building trust with customers, being able to do that is a gift, and it's something, or it's something that's a skill that you have to really develop. Um, but outside of that, I think it's really diligent strategic thinking and planning, and it's, like, thinking through what are all the moves I'm gonna make? How do I structure those? How do I rally all the resources? What is a team sport? And I do that in a thoughtful, like str- like a captain of a, of a team. And I think reps who don't, who are good-

Brett Berson 41:44 Even that are IC reps, they have to think about the world that way.

Lindsey Scrase 41:47 They have to think about the world that way, and, and they're, um, just e- exceptional at, like, the, the drive, the tenacity of executing that strategy, and they're, they're not flying by the seat of their pants. They're not doing it on their own and then being like, "Oh, I gotta bring along an SE," or, "Oh, like this is ... I didn't get approval for this last minute." I mean, I see a lot of that, but the, the great ones are, like, exceptional project managers in a way at, like, thinking through how to, how to get into the customer and, like, bring, bring all the resources around them.

Brett Berson 42:16 Going back to sort of the transition from CRO to COO Did you find it at all hard not to just spend time and focus on all the stuff you were already very good at? Like, I, I would imagine you, you spent a career in, in various flavors of go-to-market. You're very good at it because you're still doing it, and so you're the COO, but, you know, the CRO hat kinda keeps calling you back because you're, you know, really good at that thing.

Lindsey Scrase 42:41 Yeah. No, absolutely. And that's the, that's the ongoing push, you know, that I'm looking at, like, where am I spending my time working on with Daniel on, like, what are the next big strategic things we need to be thinking about? One of those, for example, is a, a company we have acquired recently, uh, or a year ago at this point, but integrating that in across the whole company and accelerating that business. So that's like a go-to-market angle, but, like, really leaning in more directly. It's hard because I don't have a CRO, so I'm still managing all of the functions, um, as a f- effective CRO, but I have, like, exceptional leaders.

Brett Berson 43:18 What else can you share about the dynamic of managing a leader that is outside of your domain? And, like, it feels like there is a difference for you coming up as a CRO managing a VP of sales than you managing a VP of marketing or CMO or whatnot.

Lindsey Scrase 43:37 Yeah, I mean, I think that I've, I've had this so many times throughout my career. I think the first times, like, I mean, um, I took over sales engineering and at one point in Google for my, my world, my segment, and I had not done that. Or, um, so I think that there's been a lot of times of this where I've kind of cut out that process of like, oh, I don't know what I'm doing. Like, can I add value? And I think it's just about, you know, as you get more and more senior, your role as a leader is to help remove obstacles, help think through strategy, help think through, like, talent on the team and structure of the team, but it's not necessarily to be a functional expert by any means. And I am very transparent in the hiring process, too, of, like, where, where I spike, where, you know, I'll partner with them or need them to lean in, and I ask the same of them. And then I think it's just having that mutual trust where, you know, I, I think that, you know, you'll flag to me, like, I won't necessarily... I'll ask, I'll push and ask the right questions or I'll ask a lot of questions. Um, and it's really 'cause I'm tr- I'm trying to learn and pressure test. But, you know, the, the trust is there that, y- you know, they know that I'm going through that process with them and asking questions to make it better.

Brett Berson 44:45 So when you look across the way, the rhythm and cadence of the way that you run your org, what are the rituals and touch points that happen weekly or daily or quarterly that are the most important things that you've put in place?

Lindsey Scrase 45:00 There's, like, the company wide and then my

Lindsey Scrase 45:03 team. For the company, at the C-staff level, we meet every single morning, um, and there's no structured agenda. And when I joined, this was already in place, and I'm like, "This is crazy. This is so much time." [laughs]

Brett Berson 45:14 A huge waste of time.

Lindsey Scrase 45:16 And I've become a convert. I mean, there's, like, you know, one time out of several that it's not, you know, maybe not as high value, but it creates that trust. It creates this opportunity for us as a leadership team to know each other as people, to know what's going on in each other's personal life, to be able to f- align on any fire that's happening, whether it's a customer issue, an engineering incident, an employee thing, very real time. And it really, like, supports that first team mentality, like this is your first team, it's not your function. So that has been, I think it's, it's, it's a key part of how we operate and, and helps us function very well.

Brett Berson 45:51 And there's, it's 30 minutes or an hour?

Lindsey Scrase 45:53 30 minutes, 30 minutes.

Brett Berson 45:54 And there's no agenda. You just show up and-

Lindsey Scrase 45:56 Yeah

Brett Berson 45:56 ... talk about whatever.

Lindsey Scrase 45:57 Yeah. There was, like, an unwritten rule in the beginning that's like the first half is about non-work stuff, but I, I'm typically the [laughs] one that's like, "All right."

Brett Berson 46:04 Let's get to work here.

Lindsey Scrase 46:05 "Let's talk about this, you guys." But it is, it is very, very conducive to building that trust I talked about earlier. Every, um, two weeks, we do a review with all of our kinda top 20 leaders of the entire business, and so that is a... We're, we're a document culture, which is, you know, we do the silent read, comment, and, and, and discuss after, and that, that review of that document is kinda the, the, the cadence by which we're reviewing.

Brett Berson 46:30 And the document's like a business review?

Lindsey Scrase 46:32 It's a business review that covers... We have, um, strategic goals we set at the beginning of the year. We spend a lot of time on those. So it, it tracks input and output metrics across all of those strategic priorities we're driving, and then it also covers some functional metrics and, like, the revenue, like the forecast or the revenue overall as a company. That is critical, and that's kind of, there's cascades up to that w- with each function. Um, I do, like, a revenue business review every two weeks.

Brett Berson 46:59 On th- but on that review, like, what is then happening? So everybody sits down and reads it, and then what's the meeting used for?

Lindsey Scrase 47:06 It's a kind of intake of information, so everyone's clear on what's happening across, and then there's a, we, and then we discuss. People flag, "Hey, I wanna discuss this," and, and so there's like, you know, five to 10 topics or any goal that's o- that's red or off track we will discuss as well. And we'll go through, um, problem solve live. You know, hey, if there's an issue, an engineering issue over here, or hey, like, there's a, a customer situation here, what do we need to do, and kind of set a DRI in place to go address and, and follow up. It's a way to, you know, make sure that we're, we're tracking with rigor. And then if, if, like, certain goals are off, like, quite off track, we will do a separate deep dive one hour where we'll go into that, and we, we do those monthly as well.

Brett Berson 47:49 And then you were saying you have every other week is a, is a revenue-

Lindsey Scrase 47:51 We have a re- like, a revenue business review, um, just on the, on the, on the revenue organization. Twice a year, we bring all our top, like, 80 leaders together in person, kind of get them aligned at the beginning of the year, like, "Here's the strategy. Here are our goals." Very intentional cascading with them, and then we do a company-wide kickoff. And then midyear as well, we meet with that set of leaders again. These are the leaders who are, like, you know, the director of demand gen or the director of platform engineering. Like, they are driving the, you know, the, the company, and we're- At that stage where we're not big enough to have, like, completely federated approach, but, you know, um, so we, we bring everyone together and, and make sure that they're aligned. That, that was a big change I made coming to Checkr, where we didn't really think about middle layers at all. It was, like, the whole company and then the, like, executive team. And so, and that's really critical to get, get people the information before it's spread to the whole company, whether it's an org change, whether it's a strategy shift.

Brett Berson 48:46 And so throughout the year, you disseminate through those 80 people?

Lindsey Scrase 48:49 Exactly. So, like, any, um, beginning of the year, middle of the year, any org change we're rolling out this, this week, like, that group gets informed before the rest of the company on anything, any policy change. We have, we have regular virtual meetings with them as well, but it's a time investment, um, but it's, like, high ROI.

Brett Berson 49:08 And is it just if you get to a certain level in the career ladder, you're auto-added to that group-

Lindsey Scrase 49:13 Yeah

Brett Berson 49:13 ... or there's a judgment piece or?

Lindsey Scrase 49:15 You're auto-added to make it s- very straightforward.

Brett Berson 49:17 And then what's the difference between that group and the top 20 people?

Lindsey Scrase 49:20 Um, the top 20 is VP and above.

Brett Berson 49:22 Okay.

Lindsey Scrase 49:22 And that top 20, um, yeah, we're meeting in person as well two, two additional times per year, just that group, usually off-site, and that's a mix of, like, setting the strategic goals for the year. Um, it is thinking, you know, kind of bringing people along on whether it's our strategy with M&A or investors, and then it's a lot of trust building as well, like how are we functioning as a leadership team. And I mean, that, that goes on... So we do this, and we do it twice a year with our C staff. So a lot of touch points intentionally built to allow us to just move more quickly in the off-season [chuckles] or just, like, as we're, as everyone's executing, that alignment is really important.

Brett Berson 49:59 Do you think if you were to be a CRO again, it, it would be marginally helpful that you had this role? Or it's like would be a big deal in terms of your overall effectiveness?

Lindsey Scrase 50:07 I'm such an operator at heart and, and so data driven in the way I've operated. It hasn't... It, it would give me, like, the bigger picture perspective, but I don't think it would, like, fundamentally change for me personally, like, the way I'm operating, uh, because I, I just have that bent

Lindsey Scrase 50:23 naturally.

Brett Berson 50:23 On sort of the data piece, what... where have you found that data has led you in the wrong direction? Or had masked something that you could only know qualitatively, or there are these, like, pitfalls if, if you get too focused on managing through a dashboard?

Lindsey Scrase 50:43 There's, like, strategic direction and product insight that you can't glean through data. I meet with customers regularly as possible, try to hear the insights from calls, and, um, fraud is an area that just keeps coming up more and more. But it wasn't shown in the data. Like, people, people are seeing more and more inadvertently hiring North Koreans into their company and, like, wondering, like, what line of code did this person change? Having someone that's stolen an SSN and is on multiple platforms. Like, so all of these things, you, you know, we kind of knew here and there, there were issues, but as I, you know, started to talk to customer A, you know, to customer B, our chief product officer and our, our sales team hearing more and more, like, that, that just gleaned from, like, you know, connecting dots and, and, and that has formed, like, a really big strategic investment for us and, like, kinda where we wanna go and, and product investment. And that's the kinda thing, if you're just focused on scoreboard and metrics, you're like, "We don't... Th- this, this, like, may not... May- maybe we've been doing this for free, or maybe this is, like, a very low... Identity verification is, like, a low ASP product. Like, we don't need to spend a ton of focus here." But it's incredibly strategic in the bigger picture. So that's, like, one example where you can't just be looking at data. You have to supplement that with customer, as many customer conversations as you can. And, and for reps who are having those calls every day, they're not in the right, like, they're not in the right role to be able to, like, share that information up or to push forward strategic direction. It has to come from you.

Brett Berson 52:17 And it... Would you say that the customer is where most goodness comes from in terms of supplementing context on top of data, or are there other pockets?

Lindsey Scrase 52:28 I think that's the, like, the ultimate gold you're trying to get. I think, like, the, you know, in terms of what's going well, what's not going well, where do we need to invest strategically for the future. There's various ways to get that, if not the customer, like the, from obviously, like the, the teams and, you know, we've, we've built a whole customer LLM that's, like, got all the knowledge on all the customer support calls and all the sales calls and whatnot, but going to direct to the source is I see, like, the highest value. And, and also, like, hearing, you know, you just, like, having that empathy ongoing is really important. And that's, that's actually pro- like, a hard part about being in the COO role, is that you're... There's obviously, like, a lot of demands for your time, but pulling you into a customer call, like, [chuckles] I said, like, "I wanna talk to, like, y- you know, as many customers per week," et cetera, et cetera. There's hesitance. Like, oh, well, when's this gonna be on the call? Like, what's the agenda? Like, what is... Like, the, like, does the customer wanna do this? Is the, you know, is the rep... So it's, it's, like, you have to really force yourself in-

Brett Berson 53:28 Mm

Lindsey Scrase 53:28 ... 'cause the, the default inclination for the team is like, "We've got this." Like, "Don't, don't bother," you know?

Brett Berson 53:34 Do you find that figuring out what the governing metrics for the company are is relatively easy? Or is it tricky? You're trying to represent, in some ways, something just enormously complex in a set of numbers, and you can't have 300 numbers, generally speaking, but you also can't have one number like revenue. A- any reflections on, like, that process of trying to kind of articulate the business in something much more numerical?

Lindsey Scrase 54:04 I think that we have probably too many metrics, [chuckles] just like mo- most companies do. We're very data and, and metric oriented. I'd say, like, the, the key is, like, starting with revenue and breaking it down into the component drivers. So, like, when, when I started, we looked at revenue by acquisition channel, but it was like, okay, no, we need to break it, like, new versus existing and- Upsell versus, any, like, retention, new logos versus, like, size of deal. All of that, like, just the math equation, the algebra is really important, and then structuring goals and owners across each of those.

Brett Berson 54:37 It feels like if you have a very-- if you have a consumption-based model with incredible NRR, you run the risk of actually under-emphasizing net new business, 'cause you can hit these incredible, you know, annual goals, and then when you pick it apart, you don't have enough new seeds being planted to blossom into big accounts in the future.

Lindsey Scrase 54:56 Yeah. No, I'm a, I'm a big proponent of, of this, and separating out your sales force into new logo hunters and then existing account reps, I think it's very problematic for a growth company to combine those into one role, which a lot of people do. And explicit goals on new customers, new revenues that there's a discrete owner for. If you're growing well and don't understand that, I think that's just as, what's the driver? It's just as bad as not growing in, in some ways, 'cause you, you don't, you don't have control over it.

Brett Berson 55:25 It's like the classic thing, if you, if you exceed plan by 20%, everybody says you're amazing. If you miss plan by 20%, everyone's very angry. But in both cases, you miss-- you were unable to predict-

Lindsey Scrase 55:39 I mean, I'd rather exceed plan, but that's-- But, but if you don't know why, I will lose trust in you. Like, you, you, you better know why you're exceeding plan. Yeah, I mean, I think that the metrics... Well, one thing that we do at Checkr is, like, there's obviously the financial metrics, like the revenue, new revenue, margin, EBITDA, which kind of govern our financial plan. But I mentioned, I mentioned earlier, we have strategic goals we set. It-- We spend a lot of time in Q4 every year, like, outlining those, deciding what those would be, and then we track those rigorously the following year. And so those are the things where they're outside the financial plan. It could be, like, percentage of, of revenue from this new product area that, like, we, we've got product markets fit, like we wanna scale it up, for example. Or it could be strategic investment in we're building, like, a people data graph, which is like just work outside. This is not directly monetizable in the short term, but it's strategic long term. So those type of things, like having those set, communicated to the company, and then everyone's like knows when you're trying to make trade-offs, like you bias toward doing these things and not the, the long list of other things. So having metrics on those is also really important so you know the, the inputs and outputs. And then we try to simplify that down to, you know, like 10 things that we've got metrics on, so those are pretty clear. And then, you know, beyond that, there's a proliferation of metrics, but having key owners of, like, you own this and all the things cascading up to it so that you have distinct accountability. I think there's nothing, like, more frustrating to me is, like, there's a metric and 12 people think they own it, or that means, like, no one owns it, and you're not gonna see movement. So you need the metric, you need a goal. And we like to set goals that are-- It's better to set a goal that's ambitious and you slightly miss than to get, like, 130% of the goal, 'cause that means

Lindsey Scrase 57:27 you weren't thinking big enough.

Brett Berson 57:28 But I feel like one of the downsides of s-setting particularly ambitious goals is, you know, there's something about this sense of as a company, we wanna feel like we're winning, and we set the goal, and we hit the goal. And, like, if you, if you do, like, the classic OKR thing where you wanna get 70 or 80%, I forget what the number is, and that's great, it doesn't create a culture of, of feeling like we're winning. Have you noticed that, or do you-

Lindsey Scrase 57:49 Yeah, no, absolutely. We've had a lot of debates about this, so similar thing. My take is similar to yours. For the metrics that matter from a financial perspective or, like, the sales team quota overall, that should be ones where we wanna hit that within, like, 5%. Strategic stretch goals and initiatives, we label them such, like, "Hey, this is a, this is a stretch goal. I want you to think ambitiously." We're doing this for H2 right now. We're saying, okay, what are some, for lack of creative term, 10X goals? But you get the gist for H2 that we know they're impossible, but I want you to think really big and think we're like, you have to rethink the way your team works. You have to, like, leverage AI in new ways to hit those. But I think it's defining them as such so that you're not in this situation where you're either losing or no one's thinking big.

Brett Berson 58:35 Yeah, 'cause to-- I think to the point that you're making, sometimes if, if the goal is 5X versus 10%, you have to fundamentally rethink everything to get a 5X. Then, you know, you can eke out a, a 10 or 20% gain in, in lots of small changes.

Lindsey Scrase 58:50 And it's really hard for someone in seat to think about completely rethinking, and so, like, you have to force them to.

Brett Berson 58:57 In the purview of y- of your part of the company, what is the way that you guys have leveraged AI that has made the biggest difference? So not, like, cool demos and all this other stuff that, like-- But, like, in production, in the way the team is running and working, it has made, like, a profound impact on, on what you all are doing.

Lindsey Scrase 59:18 Maybe starting within my organization, um, but in operations, uh, this is, like, all of our supply chain, polling data, customer support, candidate support, disputes, you know, as part of FCRA processes. All of that's being done by humans in the past. We have a incredibly AI forward-thinking SVP of operations, and his team are phenomenal. And so they've built AI, um... We've taken our AI resolution rate. We've got goals to get that to, you know, 90-plus percent over time, uh, where it's not only, like, a chatbot interaction, but it's generative AI addressing the customer issues. We've taken customer, um, satisfaction on interactions from before generative AI and, and post, like improved, like, 3X in terms of CSAT, and we've been able to substantially scale, um, without adding more headcount. And, you know, the, the, the, the per cost per, you know, revenue dollar has gone down dramatically.

Brett Berson 1:00:14 And, like, in a given day or a given week, how does that impact the business?

Lindsey Scrase 1:00:19 It allows us to know where to invest our roadmap or even what customers Maybe sh- showing signals of growth opportunity or, like, distress in some way because, hey, there's these customer support tickets, or this, like, inter-international product is picked on. Like, that's one where, hey, we're, we're seeing this come up on several calls for this country. There's, there's maybe, there's maybe an issue there. We need to, like, prioritize this more quickly to win more customers or prevent churn of this, th- these, like, 10 accounts or something like that. So it's, like, a real-time signal so that we're not in this, like, annual planning process and, and quarterly, but real-time capturing opportunities for, for growth or churn reduction. So that's great. And then also the other part is just, like, cost avoidance on the agentic side. On the sales side, we've had, I mean, AI SDRs is a basic that, that, that happened a while ago. We've done, um, building this with a partner, but an entire orchestration layer for outbound. That was an area where it's like to, to do this well, reps have, like, 20 different systems they're having to go into to do all the things. And so we built kind of one agentic layer that they use and that when they wake up in the morning, it's already outreached to specific accounts based on signals, customized content. And so we're six months into rolling that in, and obviously takes investment to continue to improve, but that's a big bet we're making.

Brett Berson 1:01:45 And has that shown tremendous promise?

Lindsey Scrase 1:01:47 It's shown promise, yeah. We-- Yeah, absolutely. And it's-- I mean, we're, our outbound pipeline is, percentage of total pipeline is continuing to grow. And another area we're, we're early in, but, like, account-based marketing, it's, like, tends to be very manual. Can we, like, hundred X that in H2 through this and other tooling we're, we're stitching together? On the engineering side as well, we're, you know, over 80% of our code is now, um, written with generative AI, and so that's another area. So there's very fundamental, like, in production use cases. Um, and then as I mentioned, we've got pretty, like, really, like, blue sky goals for H2 that if we get, like, 40% there, they'll be very meaningful. To do this well, I mean, that's the hard part. And I've seen, like, we pushed AI tools to the entire company pretty early. Like, I mean, everyone has a Claude license, a Lovable license, and we did hack days that, like, uh, non-engineering hack days to, like, drive this. And so it's like, first, like, everyone's just building stuff for their own productivity. Just like, great, but like [chuckles] costs money, and it's not-- I mean, it's maybe, maybe making you marginally more efficient. And then the push is to move people to build, like, um, an app that is business impact. Like, hey, like, hey, you know, a Customer 360 skill in Claude or agent that, you know, will help us actually have better insight into this customer. Everyone's, like, building the same thing. And so then it's like getting the shared agents that everyone's using the same one, someone centrally manages it, and then eventually, like, workflows and systems is where we need to move to 'cause we don't want AI for AI's sake. But, like, give me the signals that a customer is challenged. Send that to the CSM immediately to, like, h- activate this outreach sequence. Like, that type of thing is where we need to move toward. So we're investing a lot in the knowledge layer, um, to be able to, to query. Queryable companies, like, all the rage, um, but we're investing substantially in it.

Brett Berson 1:03:38 And so have you found that, like, a lot of the work needs to be more centralized, or have you found that it's hybrid, where you have this drumbeat of getting every line-level employee to be playing and building and tinker- Like, it feels like it's been a little bit-- Like, you've kind of gone in multiple directions, and now is it kind of we wanna try every conceivable?

Lindsey Scrase 1:03:57 We're moving toward more centralization. But it, it's important that we get everyone up to, like, a higher level of AI fluency, and so we define what those levels are and are assessing people on the moving up. But we don't need every single ops agent building an app, right? They need to be handling tickets, or we don't necessarily need every SDR to be building the n- the next app for that. So-- But, but they should know the art of what's possible, which is why there was a heavy investment up front, and they all came up with the things that, like, now we're figuring out how to scale. So we're, we're going through that journey right

Lindsey Scrase 1:04:33 now.

Brett Berson 1:04:34 If someone is a bit earlier in their career and they are thinking about, like, where do they wanna take their career and like, okay, being a COO could be really interesting based on what I'm interested in and my own set of skills, et cetera, et cetera, what's your perspective other than be excellent at the thing you're doing and continue to be excellent and grow in your role? Like, are there certain things that if in five years or seven years or at some point in the future they wanna be a COO that they should spend time on or grow in this way, or I know it's not in your purview, but you should be doing this when it s- sits outside of your role in ops or go to market or pick any function?

Lindsey Scrase 1:05:13 If you're not in a revenue, like, sales, um, track, uh, like a lot of, like, rev ops folks I meet wanna be COO. I think you gotta run revenue sales teams specifically at s- at some point. Understanding what it's-- Like, interacting with customers is important unless you're an internally on- only focused COO, which, which can be. But interacting with customers, um, having that, um, engaging and would feel-- understand what it's like to own the number, understanding the intricacies of, like, motivating and driving and running a, a sales organization. I think that there's-- it's a bigger leap to go from, you know, kind of support function to COO owning revenue if you've never done it. So I've, I've seen people who, you know, go from that to, like, being an AE, and then, I mean, that combination is huge 'cause you, you know the operational part. You've done sales or sales leadership and then-- and taking that. If you're in the, um, sales leader track or CRO track and you wanna be a CO- a COO from there, uh, you've gotta really double-click and understand the data, the numbers, which, um, you know, there are a lot of more and more sales leaders now have that, um, acumen and, and ability. But it has to be intentional, like understanding the, like, if, you know, closest to is, like, the rev ops team and the components there, thinking about the broader company metrics and spending time on that and understanding, like, what is important financially to the, to the board, to the CEO. I think often so much times, like, a sales leader just kind of is, is so narrowly focused on the quota, the number, and, and doesn't spend time getting that insight and learning. Um, and that I think would-- could be a blocker to being-- to becoming a COO at some point.

Brett Berson 1:06:56 What else maybe just to wrap up when you reflect on your own abilities and skills do you think has served you so well and allowed you to sort of grow into a COO other than just, like, hard work and intelligence?

Lindsey Scrase 1:07:10 I think it's the, the mix of, um, incredibly data-driven and operational, um, but also really care about the humans and the people. And I know that that was one thing that Daniel-- the combination that Daniel valued of, like, hey, I know that I can trust that Lindsey's gonna, like, hold, like, a lot of rigor and be as, like, you know, detail-oriented as I would be so I can step back and let go, but also really be intentional and think about the culture and the people and building trust. Like, low, low ego is really important to us at Checkr. Like, you're in it for the company's success. You're not here to build an empire, to do it for yourself. And so I think that's, that's also served me well in this context, um, because I'm really-- I really wanna make Checkr successful. I wanna make Daniel successful, and, like, that partnership and trust is really important.

Brett Berson 1:08:02 All right. Great place to end. Thank you so much.

Lindsey Scrase 1:08:03 Yeah. Thank you.