


30 Jul 2026 · 1h 8m · 30 chapters

Why enterprise expansion is harder than startups expect, and what it takes to build a focused, data-driven enterprise go-to-market (product, sales, incentives, and operating cadence).
Lindsey Scrase, COO at Checkr. Background includes years at Google Cloud (joined when Google Cloud was small/“scrappy,” with limited enablement like RevOps/SalesOps) and prior CRO experience; at Checkr she joined as CRO to lead enterprise/multi-segment, data-driven, operational sales.
Google Cloud’s early scaling without enablement; Checkr’s enterprise shift after gig/SMB success; targeted outbound to “rich niches” (e.g., large Fortune 500 car dealerships); event examples like Houston Rodeo and a Devil Wears Prada Premier in Europe.
Written by AI. May contain mistakes.
Lindsey shares her transition from large companies to startup environments and the challenges faced.
“Then on a relative basis, you join a startup as an executive.”
Discussion on the role of a Chief Revenue Officer and the expectations in a startup.
“I think that there's a few dimensions to this for me.”
Lindsey explains the importance of humility and understanding competition in a mature market.
“There's no scarier job than being the first CRO at a startup.”
Exploring the difficulties startups face when shifting focus to enterprise clients.
“I think it requires a lot of humility to understand like where are you gapped versus an incumbent.”
Lindsey discusses essential strategies for succeeding in enterprise sales, including focus and agility.
“And there's a lot of needs that enterprises have.”
Advice on how startups can effectively break into the enterprise market.
“you're kind of doing this in a repeatable fashion, but you're not getting hands-on into what specific accounts, why, how do we run targeted plays?”
Learn how startups can assess their readiness for enterprise-level challenges.
“got when they were, you know, like let's say DoorDash was one of our first customers that was a startup when we started with them.”
Discover the importance of a data-driven approach in sales and rev ops.
“Unless you have a very completely horizontal product, but even if the pliers is different.”
Understand why events are still a vital tool in enterprise sales strategies.
“Do you think it's clear that the AEs need to understand enterprise and that being an enterprise AE is different than being an SMBA or some version of a seller down market?”
Explore the challenges and adjustments when moving from CRO to COO.
“And it takes in every possible flavor of taking people to VIP thing at F1 through cocktail hours, dinners, educational.”
Learn about the importance of trust and collaboration across departments.
“That is your direct area of accountability.”
Gain insights on maintaining structure while fostering agility in decision-making.
“Like, hey, you're our chief product officer.”
The importance of defining roles and responsibilities in decision-making.
“We've also, like I tend to think there's like the whole like rapid, racy, I think sometimes it's just like too much process.”
Discussing the difficulties and nuances of hiring executive-level positions.
“Key DRI, like what is our, how are we thinking about like major product roadmap trade-offs?”
Exploring how to improve decision-making processes within organizations.
“And so I've made bad calls there, either maybe over-indexing on someone who's got a ton of relevant experience or betting on someone who's not at that exact level but has the intrinsics who couldn't turn the corner.”
The significance of leaders being close to their teams and operations.
“Like if you know how to if I trust your process of making a decision, then like hopefully you'll be right.”
Discussing effective incentive structures in sales and organizational alignment.
“to glean that, then you're often operating blind.”
Understanding the complexities of variable compensation models for sales teams.
“And we've had to like tweak some things here and there, like what's some sort of leading thing we can give them when the deal is closed.”
Investigating how to measure performance and effectiveness in various roles.
“What are the reflections you have about variable comp for sales?”
Identifying key attributes that distinguish top sales performers from others.
“And if your unit economics are working, if you've done the math right, which you should be doing, then it all makes sense.”
Explores the challenges and strategic thinking required when moving from a CRO to a COO role.
“I mean, I see a lot of that, but the great ones are exceptional project managers in a way at like thinking through how to get into the customer and like bring all the resources around them.”
Discusses the dynamics of managing leaders from different domains and the importance of mutual trust.
“And 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.”
Highlights the rituals and touchpoints that foster trust and alignment within the leadership team.
“And there's, it's 30 minutes or an hour.”
Emphasizes the value of direct customer conversations to supplement data in strategic decision-making.
“But, you know, so we bring everyone together and make sure that they're aligned.”
Discusses the challenges of establishing effective metrics to reflect complex business dynamics.
“But pulling you into a customer call, like I said, I want to talk to as many customers per week, et cetera, et cetera.”
Explores the importance of establishing strategic goals alongside financial metrics for long-term success.
“But but if you don't know why, I will lose trust in you.”
Learn how to set and communicate strategic goals and metrics effectively.
“We spend a lot of time in Q4 every year, like outlining those, deciding what those would be.”
Discover how AI can enhance operational efficiency and customer satisfaction.
“We're saying, okay, what are some, for lack of creative term, 10x goals, but you get the gist for H2 that...”
Understand the importance of centralizing AI tools for business impact.
“And the cost per revenue dollar has gone down dramatically.”
Insights on what skills and experiences are essential for aspiring COOs.
“But like give me the signals that a customer is challenged.”

Get the gist, explore an idea or ask about something said.
On In Depth, what are the key points of this episode?
Automatic transcript. May contain errors.
0:04When you go and 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. Yeah. And it feels like after a decade of doing, you know, real outscale building, you went to something very small and I've had a really prosperous sort of last four plus years. Why do you think you've kind of 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?
0:48Yeah, 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 checker, like what checker 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 foisting it on where I'm going?
1:23So I've always liked that and been excited about it. But 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 very little resources and scale. And so we had no enablement, like pretty much seven of the 10 years I was there for any of my functions.
1:59We had like very little like RevOps or SalesOps or Systems folks or anything like that. So it was really building and figuring out how to do that at scale. So when you kind of 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. There's no scarier job than being the first CRO at a startup. 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 fit?
2:34It's very difficult. It depends on who you ask. If you ask the CRO, it's the product. If you ask the CEO, it's the CRO. 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 in SMB. I really wanted someone to think multi-segment, operationally data-driven, high-velocity sales layering on top.
3:12And 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 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. What do you think is unique about building a business like that where there's already a category of 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?
3:45or it depends on maybe how you look at the checker market, but maybe when you joined, it felt like in their sub part 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? 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's 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 product go to market.
4:25Like, hey, we'll just do this. And at Checkr, I'd say 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 is six plus years ago, but had some failures where I 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.
5:04And so whether it's at Google Cloud, like innovative companies or, you know, high volume 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. At Chucker, it's where we know we are huge value-add versus like entrenched incumbents. So people, industries like staffing, gig, retail, hospitality, manufacturing, we're doing a lot of hiring and they need the benefits of our technology and accuracy and scale. So that focus is really important.
5:40And then the other thing is the company, the whole company has to be behind it. I've kind of said this multiple times, but I can't reinforce it enough. At Checker a few years ago, we said, let's go into enterprise again. We're evaluating the strategic decision because it's an investment of resources and really our indie team's time. and we had to like literally like shake hands around the table that you know in engineering and product in legal and people 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 we have our chief product officer is meeting with customers daily.
6:24Our product managers are on the calls with our customers daily with us to really get that very fast cycle and loop of feedback to know, we're still building. And, you know, if you're a challenger, you have to be able to be agile and you can't just assume you have the right product. And there's a lot of needs that enterprises have. So it's a huge undertaking and one that, you know, Google Cloud has been obviously very successful at. Checker is, I think we're seeing a lot of success as well over the, in our most recent few years here, and a lot more to come. 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.
7:09And 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 mid-market customer. We're just going to 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 themselves up over trying to sort of dominating enterprise. Why is it actually much harder than someone imagine you have this great product and this go to market that's working to sell it to call it 200 person companies.
7:47And now you're selling to 25 ,000 person companies. I think that why is it hard? And 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 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 cycles only come up every so many years, and they're often a year-plus long sales cycle. And why, though? The decision-making process at large companies is long. There's shifting, often big decisions like this. Like, if you're going to switch your cloud provider, if you're going to switch your email provider, switch your background, your verifications platform, this takes a lot of internal resources as well from an engineering or development timelines perspective.
8:35So it has to align with the timing of their contracts. It has to align with their strategic priorities as a company. And if they're not, this isn't something they care about on the top 10 list, then you've got to figure out how to make it up there. 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 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 very complex sales cycle where you're building trust, you're multi-threading, or if you're talking to the HR buyer, you've got to figure out, okay, well, who's the ultimate decider here?
9:22Is it the CHRO? Is it the CFO? Is it the CEO? You're doing reconnaissance across the company to try to really get a good understanding. So there's a lot of challenges on the go-to-market itself. And you may be faced with lack of brand awareness and enterprise, especially if you're coming from being a 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's a different audience. And then like I mentioned, the product roadmap. Enterprise customers, there's always going to be the last long tail of requests for any customer.
9:59They're rarely buying it off the shelf. There's going to be something unique for their instance. And I mentioned like in G Suite or Google Workspace, there is things we thought product was complete and done. But the list of, you know, whether they're regulatory 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 all the reasons why it's very challenging. I think that what can make one successful in this is 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.
10:44And oftentimes, I think where people can go wrong is anything this customer asks for or prospect asks for, like, I'm going to commit to building. So suddenly your product roadmap is complete snowflakes for every single customer, which is not going to work. You just spread too thin. And on the flip side, or you're too arrogant and say, hey, we don't need to do any of this. And you can't close anything. You can't close the deals. And then it's like product and sales pointing fingers, like where is the issue? The other part I mentioned is focus and making sure that, you know, I've seen enterprise sales leaders fail where you're running sales teams.
11:22you're kind of doing this in a repeatable fashion, but you're not getting hands-on into what specific accounts, why, how do we run targeted plays? So for Checkr, for example, like getting the outbound motion, if you're going through enterprise, you have to get outbound pipeline generated. When I came in, it was not working. I'm like, okay, is this a strategy issue? Is it an execution issue? It 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 kind of tinker with it to find the right thing.
11:58But eventually figuring out and really getting laser targeted and 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. I get 100 emails a week from people trying to sell me something. I don't read any of them. And so you really got to get creative and 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 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 a hold of them.
12:39And then and then like running that sales cycle, you know, and being tenacious throughout what could be a year or year plus. So where do you think a company should start? Let's say you have a lot of success. You're at a couple hundred million dollars in a mid-market business and you want to go build an enterprise business. How do you break that apart? Just in the way that you articulate it, it's so multifaceted. 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? Translatable for any company. It's figuring out, do we have the right people on the bus?
13:16so to speak. So hiring enterprise experienced sellers is very different. Thinking about enterprise marketing is completely different than traditional growth marketing and demand generation. So you need account-based marketing, you need events, strategies, etc. Having the right product and engineering investment to be able to do last mile needs 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. I'm like, okay, we're good.
13:59We'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 started with them. They're now obviously a large enterprise, but just because you've scaled with that company doesn't make you enterprise ready. And so focusing on four 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. Like that's one where let's just keep taking them down as an example. How did you figure that out?
14:34You need a really data driven rev ops and sales team. We got like very, very granular are 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 starting to see good takedowns in a specific, we call them rich niches. But then let's spin up more and more campaigns targeting that. And like, you know, you have referenceable customers, you're seeing good takedown strategy. 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 pray and you're trying to find these niches?
15:16Or you need to find a more efficient path to start to stack the niches on top of one another? I would look at where are you performing well in the mid-market. Do a really deep vertical analysis. Talk to customers. No, where are you acquiring customers really well? Were they thriving? your NRR is high, GRR is high, and then start there in a few areas, I wouldn't kind of go tackle the beast head on because it's a lot of money and you want to 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 if the pliers is different.
15:58When you think about sort of 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 kind of 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 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.
16:32But 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, if we're going to do this, we need one dedicated product manager, because there's not an enterprise. 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 product, that just helped us move and scale so much more quickly. So I think having some separation is helpful.
17:05And 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. Did you find that you had to pre-commit to X number of roughly, we're going to spend a third of our engineering resources on what's coming from the go-to-market and product team that's with enterprise or it was much more organic? It was more organic. And every quarter we're looking at that breakdown. And what we did align on is that there's going to be an unanticipated work that we're going to have to do. And we all need to align that. Like, we've got to figure out how to do that.
17:36Because even at the beginning of a quarter, you set a roadmap, but there's stuff that's going to come up from a new prospect where we've got to figure out how to fit it in or an existing customer that we just ramped. Because there's a lot of unknowns at that point still. Do you think it's clear that the AEs need to understand enterprise and that being an enterprise AE is different than being an SMBA or 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?
18:17I 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 Checker. And at that point, we weren't going big in enterprise. So for me, it was really important to hire a sales leader who had done this multiple times and done it in an environment that was gritty and challenging, not where, hey, they're the market leader running an enterprise org. And 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 so that, I think, is very important. And then on the sales reps, we've got a great internal mobility program where you can grow from being an S &B commercially up into enterprise.
19:01But what's very hard to train if they don't have it already is that outbound demand generation hunger. So if you're taking and hiring someone, even an 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'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 the phones or doing outbound without like a fresh, warm book. 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.
19:40And 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 it's very effective and it's generally very high ROI. What's going on with like events and selling products and why they tend to work very well? regardless of who the buyer is or you could go through, and it just tends to work well. Yeah. I mean, I also, you know, especially post-COVID, like events were dead. We stopped doing anything. And then we piloted it and saw returns, watched it closely, and over the years have invested substantially in this.
20:22I think that the crux of it is like a sale is a, it's 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 career, this is a big strategic thing you're recommending internally. You don't want to, 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. I don't think anytime soon, in enterprise sales specifically, that's going to be replaced like the AI or on the agentic side. But it's that human-to-human contact is kind of the biggest fundamental pillar.
20:57And then I think also in where we try to focus our events is giving people something that they wouldn't get otherwise. So like I'm sure you get invited to events, 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 Houston Rodeo or Devil Wears Prada Premier in Europe, just something that's different or like very strong thought leadership that's going to help you in your job.
21:37And so it can't just be like go to the same event. It's got to be targeted 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 that's hugely valuable for them. So events are not dead. And I don't think they're dying anytime soon. If you think about going from CRO to COO in the context of Checkr, what was by far the hardest parts of that?
22:13The mental shift, especially in a large company like Google, even though we were Google Cloud, smaller when I joined, but you're managing your own functions and 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 myself into other people's business who were not on my team. So, like, let's look at the supply chain, you know, which is owned by another function at that time. Like, how can we improve that? or our recruiting velocity, our hiring approach. Is this working well? Hey, let me partner with you on that.
22:46Looking at our metrics. Like I, from with our CFO at the time, like, hey, 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 an adjustment, especially like, no, those people don't, those are my peers objectively, but I had to lean in and push them. And then also working with Daniel, You know, he we spent a lot of time intentionally on a few things, but one is continuing to build trust, continuing to give him feedback. And he wants to be pushed as well. Give like feedback both ways, obviously. And then figuring out the right balance of running the like I do our company business reviews and, you know, and he sat back more.
23:30But making sure that he's he's a founder. He cares deeply this is his baby 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 he and I are always working through that and finding the right balance to make sure we're on the same page. 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? Or like, very easy to get defensive, very easy to get territorial. Very easy for you to like, for that person to then say, well, let's talk about your part of the, you know, or like all of the interpersonal things.
24:14I think it starts with trust 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 C staff, it's the six of us, including the CEO. But when, you know, we do offsites together and like ways to connect in a deeper level so that we can have difficult conversations. Same with our VP level, our director level, all of that I coordinate. But so that's a big part of it where you can, you have the license to push each other. The second is that I had to get out of my own way.
24:50And like, this is my job. I debate. I push. But I like harmony. And, you know, I had to tell people explicitly what I was doing. Like, hey, this is my job as COO. I'm, you know, I want to partner with you. Like, this is, we're like a lot, we're working on this together. I don't have the right answers always. And I get a lot of benefit when they push me. Like, hey, you're our chief product officer. And he came, he's like, you're the sales collateral is not very good. He's like a very strong enterprise focus product leader. And you're right. Let's like go improve this together. So there's some, there's, you know, it should go both ways.
25:27I think that 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 issues over here. This builds on what you were saying a second ago about, you know, building cadence and systems and processes you scale. And it feels like 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 you have this fundamental tension where you're trying to figure out how do we have as little work around the actual work that people want to do?
26:11But 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 and sort of those two things? Yeah. I mean, decision making is one we've been actively working through right now. And that's a very hard one because 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 getting work done.
26:57And 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 I think at Checker 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. And so we've worked to try to turn that in an intentional way and just like very practical things. But first of all, Daniel and I sat down a couple of years ago and said, OK, what what are the decisions that you need to make? Let's just document it. So what are some examples of that?
27:34Like deals above a certain size or any major brand campaign, not like a demand gen, but like any major brand decision, any product monetization that's going like in a completely like we're a consumptive model. Like changing a product to SaaS is an example. Our CEO cares about swag. It's like what we put out there, people are wearing. 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, you know, the next layer, the next layer. So there's that. We've also, like I tend to think there's like the whole like rapid, racy, I think sometimes it's just like too much process.
28:11But what we've rolled out is two things. One, for every initiative or anything happening, like who's the DRI, directly responsible individual. And that's just in our lexicon because we saw a lot of like swirl happening around like unsure who is taking the next step to own something. Codifying who is the decision maker because we saw naturally everything was just flowing up. And then it wasn't always obvious that certain executives were deciding everything or everything was flowing up to VPs. And so it forces us to say like, oh, wow, this I'm the decision maker on a lot of things like push it down.
28:44Like as an executive, as a leader, how I think about my time is the ROI of my time on a decision should be high. So I should be able to do distinctly better than someone below me or deeper in the organization. And if I'm deciding things down there, then I'm not getting shareholder value. And so that's like one big thing we put in place in terms of like mechanism to flow decisions. And so 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?
29:23Key DRI, like what is our, how are we thinking about like major product roadmap trade-offs? Like that's probably the thing we disagree and debate on the most as a company. There's so many massive opportunities ahead of us. We could go run after and capture revenue very quickly. How do we sequence those? What do we not do? So that's at the exact level decision because it really should tie to our three-year roadmap and strategy. 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 and going into next year? We're going through that decision right now.
30:01And 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 going to make the right decision. Big M &A is one where those are one-way doors that are hard. And then hiring is really important. So key, any VP level and above, if you get that wrong, that's going to obviously have a ripple effect on the whole company. I have to do it too. I'm a perfectionist. I am very data-driven. And I always tell people, once I have your trust, you go make the decisions.
30:44when I have a new hire, a new leader, I'm investing more time up front. Like here's how I would make a decision. Here's, you know, like 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. 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, then it's oftentimes very hard to get it right. I think hiring is one of the hardest things, especially executive hiring. People just are really good interviewers at that stage in their career, and the stakes are high.
31:27And so I've made bad calls there, either maybe over-indexing on someone who's got a ton of relevant experience or betting on someone who's not at that exact level but has the intrinsics who couldn't turn the corner. And negotiations with very high stakes where there's not perfect information and there's no perfect decision. And I think that what I've learned over the years is that 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 recovering perfectionist, It's like you're going to make the best decision you have with the information you have available and you have to make a decision.
32:16Nothing 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 10 out of 10, you probably will. But there will be some misses and I might have had the same outcome. Do you find that even 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.
32:52And so you have to stay close to the metal. Absolutely. 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 and 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 kind of hear through osmosis what's happening talking to people in the hallway etc 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 can regularly keep pulse of everything.
33:28Getting 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. We're just like sitting over here like pontificating. 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.
34:05I've seen this in both ways. I've been like, you know, in an organization where people are making decisions with completely lacking context. 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, there's so many important things as it relates to running a go-to-market team and figuring out things like comm. What are some of the things that you figured out as it relates to incentive design or 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?
34:41I mean, the biggest experience I've had in this and learnings has been in the like sales compensation and moving from a 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 going to spend. And so I've lived through this transition twice now. When I came into Checkr, people were comped on bookings. It's like how much the customer is going to spend. How much do you think they're going to spend?
35:17In reality, we don't collect revenue until based on like how many checks they're running. And so we, 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. And then therefore, I know like if you're comped on this, you're aligning, you know, your pay is aligning with value to the customer, which is then aligning with revenue to Checker. And we've had to like tweak some things here and there, like what's some sort of leading thing we can give them when the deal is closed.
35:58But it's been a game changer in terms of the way like customer engagement, because we're doing what's right for them. 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 not getting incented on anything. Like if I'm pumping my sales that are on total revenue for the company.
36:33It's like, that's not, you know, high leverage for me. And then, you know, just giving them the guardrails so that we don't go 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 it's like these decisions are easy. Like, should we add more reps? Like, how do we treat this one deal? Like, 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 founders or for leaders, like a sales leader will come in and say like, no, no, no, we need to do it this way.
37:08And like, no, you don't. Really think first principles. What are the reflections you have about variable comp for sales? Because I feel like you have a bunch of, you know, founders that want to 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. And I've always wondered, why aren't more PMs on variable comp? And why aren't we pick any of these functions?
37:41Yeah, I mean, I haven't thought deeply about the product or other functions like engineers. But on the sales side, absolutely, they should be on variable comp. And by nature, you want people who are incredibly competitive, hungry, and who are going to take this risk of 50 % of their compensation is at risk. Like sometimes I get asked, like, why do salespeople make so much? I'm like, you want to go take a quota and have your salary cut in half? Like, have at it, right? I feel like that would be interesting. 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.
38:20I think the hard thing there, which is, I think, love any thoughts you have, but measuring the effectiveness of the… Inputs and outputs. Yeah, is hard. And like 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? You know, it's harder. I think the harder it is to have that scoreboard that you can look at objectively, the harder it is to put on a variable comp. But when you are very clear on it, 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.
38:52It works well. There's like MBO plans where you're I've done those for certain roles where it's like it's like five categories and 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 a is is like a hot commodity they can go other places if they know there's going to make a lot more money or be more successful somewhere else they'll vote with their feet and so you want to have a good plan where there's a lot of upside and that's another thing we've looked at it's 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 going to go to accelerator accelerator mode, we've had times where there's caps on that or we're stingy on that.
39:40It's like, that's not the right move. Like, to what end? And if your unit economics are working, if you've done the math right, which you should be doing, then it all makes sense. Like, this math works. I think people, like, the highest performing AE should make a lot more than a lot of people in the company. It does feel like the fact that 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.
40:18And yeah, you have career ladders and this and that, but it doesn't work the same way as sellers. I think that's where things are moving more and more is differentiating, paying more for performance across all roles. And especially with, you know, with like leveraging AI, You can get like 10x more out of a certain amazing engineer than an average one. In working across so many sellers, what's kind of 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 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?
41:02People like have the misconception about sellers. They're like, oh, it's the most like outgoing guy over there that's going to be the best seller. A lot of them are very introverted, I find. They have to turn it on. Yeah, exactly. And then need to re-energize. It's probably two ingredients for me. I mean, like building trust with customers, being able to do that is a gift. And it's something or something that's a skill that you have to really develop. 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 going to make?
41:32Like, how do I structure those? How do I rally all the resources? It was a team sport. And I do that in a thoughtful, like a captain of a team. And I think reps who don't, who are good. Even that are IC reps, they have to think about the world that way. They have to think about the world that way. And they're just exceptional at, like, the drive, the tenacity of executing that strategy. And they're not flying by the seat of their pants. They're not doing it on their own. And then be like, oh, I got to 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 great ones are exceptional project managers in a way at like thinking through how to get into the customer and like bring all the resources around them.
42:16Going 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're already very good at? Yeah. Like I would imagine you spent a career 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 kind of keeps calling you back because you're, you know, really good at that thing. Yeah, no, absolutely. And that's the ongoing push, you know, that I'm looking at. Like, where am I spending my time working on with Daniel? And like, what are the next big strategic things we need to be thinking about?
42:54One of those, for example, is a company we have acquired recently 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 as an effective CRO, but I have exceptional leaders. What else can you share about the dynamic of managing a leader that is outside of your domain? And 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.
43:37Yeah, I mean, I think that I've had this so many times throughout my career. I think the first times, like, I mean, I took over sales engineering and at one point in Google for my world, my segment, and I had not done that. Or 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.
44:12but 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. And it's really because I'm trying to learn and pressure tests, but you know, that the trust is there that, you know, they know that I'm going through that process with them and asking questions to make it better.
44:45So 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? There's like the company-wide and then my team. For the company, at the C-stuff level, we meet every single morning 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. 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.
45:26It 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 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 a key part of how we operate and helps us function very well. And there's, it's 30 minutes or an hour. 30 minutes. And there's no agenda. You just show up and talk about whatever.
45:57Yeah. There was like an unwritten rule in the beginning that's like the first half is about non-work stuff, but I'm typically the one that's like, all right, let's talk about this, you guys. But it is very, very conducive to building that trust I talked about earlier. Every two weeks, we do a review with all of our kind of top 20 leaders of the entire business. And so that is a, we're a document culture, which is, you know, we do the silent read, comment, and discuss after. And that review of that document is kind of the cadence by which we're reviewing. And the document's like a business review?
46:32It's a business review that covers, we have strategic goals we set at the beginning of the year. We spend a lot of time on those. So 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, the revenue overall as a company. That is critical. And that's kind of, there's cascades up to that with each function. I do like a revenue business review every two weeks. But on that review, like what is then happening? So everybody sits down and reads it. And then what's the medium used for?
47:06It'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 want to discuss this. And so there's like, you know, five to 10 topics or any goal that's that's read or off track. We will discuss as well. And we'll go through problem solve live. You know, hey, there's an issue, an engineering issue over here. Hey, like there's a customer situation here. What do we need to do? And kind of set a DRI in place to go address and follow up. It's a way to make sure that we're tracking with rigor. And then 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.
47:47And we do those monthly as well. And then you were saying you have every other week is a revenue. Like a revenue business review just on the revenue organization. Twice a year, we bring 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 mid-year 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, you know, the company.
48:19And we're at that stage where we're not big enough to have like completely federated approach. But, you know, so we bring everyone together and make sure that they're aligned. 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 executive team. And that's really critical to get people the information before it's spread to the whole company, whether it's an org change, whether it's a strategy shift. And so throughout the year you disseminate through those 80 people? Exactly. So like any beginning of the year, middle of the year, any org change we're rolling out this week, like that group gets informed before the rest of the company on anything.
49:00Any policy change, we have regular virtual meetings with them as well. But it's a time investment, but it's like high ROI. And is it just if you get to a certain level in the career ladder, you're auto-added to that group or there's a judgment piece? You're auto-added just to make it very straightforward. And then what's the difference between that group and the top 20 people? Um, the top 20 is VP and that top 20, um, yeah, we're meeting in person as well. Two, two additional times per year, just that group, usually offsite. 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.
49:41And then it's a lot of trust building as well. Like how are we functioning as a leadership team? and I mean that goes 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 or just like as we're as everyone's executing that alignment is really important. Do you think if you were to be a CRO again 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? I'm such an operator at heart and so data driven and the way I've operated it hasn't 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 because I just have that bent naturally.
50:23On sort of the data piece, 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 you get too focused on managing through a dashboard? There's like strategic direction and product insight that you can't glean through data. I mean, with customers regularly as possible, try to hear the insights from calls. And 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 wondering what line of code did this person change?
51:08having someone that's stolen an SSN and is on multiple platforms. So all of these things, 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, customer B, our chief product officer and our sales team hearing more and more like that, that just gleaned from like, you know, connecting dots. And that has formed a really big strategic investment for us and kind of where we want to go and product investment. And that's the kind of thing, if you're just focused on scoreboard and metrics, you're like, we don't, this like, maybe we're doing this for free.
51:43Or 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 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. And would you say that the customer is where most goodness comes from in terms of supplementing context on top of data or their other pockets?
52:27I think that's 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 that from obviously like the teams. And, you know, 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 sources, I see like the highest value. And also like hearing, you know, you just like having that empathy ongoing is really important.
52:59And that's actually probably a hard part about being in the COO role is that there's obviously a lot of demands for your time. But pulling you into a customer call, like I said, I want to talk to as many customers per week, et cetera, et cetera. There's hesitance. Like, oh, well, when's this going to be on the call? What's the agenda? Is the customer want to do this? Is the rep? So it's like you have to really force yourself in because the default inclination for the team is like, we've got this, like, don't bother, you know. Do you find that figuring out what the governing metrics for the company are is relatively easy?
53:41Or 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. any reflections on like that process of trying to kind of articulate the business in something much more numerical i think that we have probably too many metrics it's like 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.
54:34And then structuring goals and owners across each of those. 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 because 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. Yeah, no, I'm a big proponent of this and separating out your Salesforce 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.
55:16If you're growing well and don't understand that, I think this just is what's the driver. It's just as bad as not growing in some ways because you don't you don't have control over it. It's like the classic thing. If you if you exceed plan by 20 percent, everybody says you're amazing. If you miss plan by 20 percent, everyone's very angry. But in both cases, you miss you are unable to predict. I mean, I'd rather exceed plan. But but if you don't know why, I will lose trust in you. Like you better know why you're exceeding plan. Yeah, I mean, I think that the metrics, one thing that we do at Chucker is like there's obviously the financial metrics, like the revenue, new revenue, margin, EBITDA, which kind of govern our financial plan.
55:58But I mentioned earlier we have strategic goals we set. We spend a lot of time in Q4 every year, like outlining those, deciding what those would be. And then we track those regularly the following year. And so those are the things where they're outside of the financial plan. It could be like percentage of revenue from this new product area that like we've got product markets fit, like we want to 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.
56:32So 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're biased toward doing these things and not the long list of other things. So having metrics on those is also really important so you know 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. So like you own this and all the things cascading up to it so that you're having distinct accountability.
57:07I think there's something 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 going to 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. Because that means you weren't thinking big enough. But I feel like one of the downsides of setting particularly ambitious goals is, you know, there's something about this sense of as a company, we want to feel like we're winning. And we set the goal and we hit the goal.
57:39And like, if you if you do like the classic OKR thing where you want to get 70 or 80 percent, I forget what the number is. And that's great. It doesn't create a culture of feeling like we're winning. Have you noticed that? Yeah, absolutely. We've had a lot of debates about the 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 want to hit that within like 5%. Strategic stretch goals and initiatives, we label them such like, hey, this is a stretch goal. I want you to think ambitiously.
58:11We'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 a situation where you're either losing or no one's thinking big. Yeah, because I think to the point that you're making, sometimes if the goal is 5x versus 10%, you have to fundamentally rethink everything to get a 5x, then you can eke out a 10 or 20 % gain and lots of small changes.
58:50And it's really hard for someone in SEAT to think about completely rethinking. And so you have to force them to. In the purview 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, but like in production, in the way the team is running and working, it has made like a profound impact on what you all are doing. It was already within my organization, but in operations, this is like all of our supply chain, polling data, customer support, candidate support disputes, you know, as part of FICRA processes.
59:29All of that's being done by humans in the past. We have an incredibly AI forward thinking SVP of operations and his team are phenomenal. And so they've built AI, we've taken our AI resolution rate, we've got goals to get that to 90 plus percent over time, where it's not only like a chatbot interaction, but it's generative AI addressing the customer issues. We've taken customer satisfaction on interactions from before generative AI and post, like improve like 3x in terms of CSAT. And we've been able to substantially scale without adding overhead count. And the cost per revenue dollar has gone down dramatically.
1:00:14And like in a given day or a given week, how does that impact the business? It allows us to know where to invest our roadmap or even what customers might be showing signals of growth opportunity or like distress in some way. Because, hey, there's these customer support tickets or this like international product is picked on. Like that's one where, hey, 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 visit 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 aisdrs is basic 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.
1:01:38And so we're six months into rolling that in. It obviously takes investment to continue to improve, but that's a big bet we're making. And has that shown tremendous promise? It's shown promise. Yeah. 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 early in, but like account-based marketing, it's like, it tends to be very manual. Can we like 100x that in H2 through this and other tooling we're stitching together. On the engineering side as well, we're, you know, over 8 % of our code is now written with generative AI.
1:02:13And so that's another area. So there's very fundamental, like in production use cases. 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, like 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 costs money and it's not, it's maybe making you marginally more efficient.
1:02:51And then the push is to move people to build like an app that is business impact. Like, hey, you know, a customer 360 skill and clawed or agent that 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 because we don't want AI for AI's sake. But like give me the signals that a customer is challenged. challenge. Send that to the CSM immediately to like activate this outreach sequence.
1:03:28Like that type of thing is where we need to move toward. So we're investing a lot in the knowledge layer to be able to query, queryable companies, like all the rage. But we're investing substantially in it. 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 tinkering? 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 want to try every conceivable? We're moving toward more centralization, but it's important that we get everyone up to like a higher level of AI fluency as we define what those levels are and are assessing people on the moving up.
1:04:10But 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 next app for that. So, but they should know the art of what's possible, which is why there was a heavy investment upfront. And they all came up with the things that like now we're figuring out how to scale. So we're going through that journey right now. If someone is a bit earlier in their career and they are thinking about like, where did they want to 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.
1:04:48Laura, 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 want to 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 sits outside of your role in ops or go to market or pick any function. If you're not in a revenue like sales track, like a lot of like rev ops folks I meet want to be COO. I think you got to run revenue sales teams specifically at some point.
1:05:27Understanding what it's like interacting with customers is important. Unless you're an internally only focused COO, which can be. But interacting with customers, having that engaging and understanding what it's like to own the number. understanding the intricacies of like motivating and driving and running a sales organization i think that there's it's a bigger leap to go from you know kind of support function to co 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 because you know the operational part you've done sales or sales leadership and then and taking that if you're in the sales leader track or cro track and you want to be a COO from there, you've got to really double-click and understand the data, the numbers, which, you know, there are a lot of more and more sales leaders now have that acumen and ability, but it has to be intentional, like understanding the, like, if, you know, closest to is like the RevOps team and the components there, thinking about the broader company metrics and spending time on that and understanding what is important financially to the board, to the CEO, I think often so much times like a sales leader just kind of is so narrowly focused on the quota, the number, and doesn't spend time getting that insight and learning.
1:06:51And that I think would could be a blocker to being to becoming a COO at some point. 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? I think it's the mix of incredibly data-driven and operational, 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 Lindsay's going to like hold like a lot of rigor and be as 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.
1:07:39And building trust, like low ego is really important to us at Checker. 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 also served me well in this context because I really want to make Checker successful. I want to make Daniel successful. And like that partnership and trust is really important. Great place to end. Thank you so much. Yeah, thank you.
1:08:11Thank you.
In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr. Before joining Checkr as CRO and later stepping into the COO seat, Lindsey spent nearly a decade at Google Cloud as global managing director for SMB, mid-market, and startups. In this conversation, she breaks down why moving upmarket into enterprise trips up so many startups looking to scale, how Checkr rebuilt its sales compensation model to keep pace with growth, and where AI is already reshaping her operations and go-to-market teams.
In today's episode, we discuss:
Why operators who thrive at massive-scale companies often struggle when they join a startup
The hard-won lessons from Checkr's early enterprise push that nearly failed
Why Checkr’s C-suite meets every morning with no specific agenda
The surprising challenges moving from CRO to COO
How Checkr turned AI experiments into operating systems
References
Amazon: https://www.amazon.com
Checkr: https://checkr.com
Claude: https://claude.com
Daniel Yanisse: https://www.linkedin.com/in/yanisse/
DoorDash: https://www.doordash.com
Google: https://www.google.com
Lovable: https://lovable.dev
Microsoft: https://www.microsoft.com
Where to find Lindsey
LinkedIn: https://www.linkedin.com/in/lindsey-scrase-0702442/
Twitter/X: https://twitter.com/Lscrase
Where to find Brett
LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
Twitter/X: https://twitter.com/brettberson
Where to find First Round Capital
Website: https://firstround.com/
First Round Review: https://review.firstround.com/
Twitter/X: https://twitter.com/firstround
YouTube: https://www.youtube.com/@FirstRoundCapital
This podcast on all platforms: https://review.firstround.com/podcast
Timestamps
00:00 Introduction
00:06 Why big-company executives often struggle in startups
02:18 What Checkr's first CRO needed to accomplish
03:33 How to take on an entrenched category leader
06:58 Why leaders underestimate how hard the jump to enterprise really is
10:23 Separating a true deal-blocker from a customer's nice-to-have request
18:30 Why Lindsey hired enterprise-scarred sales leader over a market leader's résumé
22:08 The biggest challenges of moving from CRO to COO
28:03 Why Checkr names a single decision-maker for every major decision
34:42 Why Checkr rebuilt their sales compensation model
40:39 What actually separates a team's best seller from everyone else
45:03 Inside Checkr’s daily, no-agenda, c-suite meeting
50:23 How following data can sometimes lead you in the wrong direction
57:27 Why hitting 130% of a goal isn’t always a good thing
58:57 Where AI has changed how Checkr's teams operate day to day
1:04:33 Advice for all aspiring COOs