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

Brett:

When 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. And it feels like after a decade of doing real at scale building, you went to something very small and have had a really prosperous 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 it doesn't go particularly well?

Lindsey:

Yeah. I mean, it often doesn't go well. You're right. I think that there's a few dimensions to this for me. I think there's me as a person and then there's the experience I've had and then Checkr and what Checkr needed versus what I was bringing. I think me as a person, I have always really enjoyed going into completely new contexts and understanding first principles, but even just being an expat in a different country, immersing myself in a new experience, what are different ways of doing things and really learning from that versus taking my point of view and foisting it on where I'm going. So I've always liked that and been excited about it. At Google, I joined Google Cloud when we were a few hundred people on the go-to-market side, a few hundred million in revenue, and so not dissimilar to the size and scale that Checkr is.

People think Google had a ton of resources. Obviously we do. Unlimited funding in some ways for the startup, that was Google Cloud, but it was very hands-on, scrappy, building and scaling with very little resources and scale. And so we had no enablement pretty much seven of the 10 years I was there for any of my functions. We had very little 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 take that to the Checkr context, we had a lot more built out, frankly, at Checkr when I joined than I had at the similar stage at Google. So there was that. And then I think that what Daniel was looking for... I joined as CRO. He had had several CROs before then.

Brett:

There's no scarier job than being the first CRO at a startup.

Lindsey:

It's a terrifying job. First to blame when numbers aren't hit, which is hard. Is it the person or is it the product market fit? It's very difficult.

Brett:

It depends on who you ask. If you ask the CRO, it's the product. If you ask the CEO, it's the CRO.

Lindsey:

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 were looking to... We'd kind of dabbled in enterprise, we could summon mid-market, starting an SMB, and really wanted someone to think multi-segment, operationally data-driven, high velocity sales layering on top. And so that was something where... I knew what he was wanting to buy, I was selling. There was 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.

Brett:

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? Or it depends on maybe how you look at the Checkr market, but maybe when you joined, it felt like in their sub-part of the market, they were the category leader. What are your reflections on business strategy, order of operations when you're trying to go after a market with a clear leader already?

Lindsey:

I think it requires a lot of humility to understand where are you gapped versus an incumbent? With Google, we're going up against a 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 the investment we need to make in marketing and the investment we need to make in product go to market, like hey, we'll just do this. And at Checkr, I would say it's been similar over the years where we early lead in all of the gig economy, high-volume hiring, and then shifted to enterprise. And again, this is six plus years ago, but had some failures where thought like, "Hey, we can just do this. Enterprise is the same," and it's absolutely not, and you have to think about it in terms of focus, I would say is very important. You can't go from being a challenger in the market to capturing everything overnight, but really thinking about where is that focused vertical or verticals where you know you can win.

And so whether it's at Google Cloud, like innovative companies or high volume or high growth startups is where we really leaned in. Those will become the big companies and they were going immediately to cloud, not shifting from on-prem to cloud. So that was a big part of the strategy. At Checkr, it's where we know we are huge value add versus entrenched incumbents. So 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. And then the other thing is the whole company has to be behind it. I've kind of 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 evaluating the strategic decision because it's an investment of resources and really our R&D team's time, and we had to literally shake hands around the table that 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 really tight learning loop is probably the other most important thing where we have our chief product officer is meeting with customers daily, our 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 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 Google Cloud has been obviously very successful at. Checkr, we're seeing a lot of success as well in our most recent few years here and a lot more to come.

Brett:

This topic that comes up with so many scale-up startups, which is you generally build the business on the back of venture back tech or mid-market buyers. And then at some point everyone realizes that 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 themself up over 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 and now you're selling to 25,000 person companies?

Lindsey:

I think that why is it hard, I mean, 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. It's like a set list of accounts we go after. 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.

Brett:

And why though?

Lindsey:

The decision-making process at large companies is long. Often big decisions like this, 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. So it has to align with the timing of their contracts, it has to align with their strategic priorities as a company, and if this isn't something they care about, it's on the top 10 list, then you've got to figure out how to make it up there. And so even that discovery with the customer to try to find and uncover pain and 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? Is 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 in enterprise, especially if you're coming from being a scale-up or startups know you only. There could be billboards all over San Francisco, but your buyers are in Dallas and Atlanta and Chicago, so it's a different audience. And then I mentioned the product roadmap. Enterprise customers, there's always going to be the last long tail of requests for any customer. They're rarely buying it off the shelf. There's going to be something unique for their instance. And I mentioned in G Suite or Google Workspace, there is things... We thought product was complete and done, but there's a list of whether they're regulatory or certifications that are needed for certain industries or just 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. And oftentimes I think where people can go wrong is anything this customer asks for or prospect asks for, 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 when you just spread too thin, and the flip side, or you're too arrogant and say, "Hey, we don't need to do any of this," you can't close the deals, and then it's like product and sales pointing fingers at where's the issue.

The other part I mentioned is focus and making sure that... I've seen enterprise sales leaders fail where you're running sales teams, you're 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, 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?" Took 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 tinker with it to find the right thing, but 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 a hundred emails a week from people trying to sell me something. I don't read any of them.

And so you really got to get it creative and figuring out, and especially in today's world of AI slop outbound in terms of people's attention is more distracted than ever, how do you 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... What's the pain they have and how do I address that and get ahold of them? And then running that sales cycle and being tenacious throughout what could be a year or a year-plus.

Brett:

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'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?

Lindsey:

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 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, et cetera. Having the right product and engineering investment to be able to do last mile needs and build for the enterprise specifically. So those are table stakes. And then the how is to start in a focused approach. You can't spray and pray.

And so often people will have a small pilot in a specific large enterprise and like, okay, we're good. We're in the enterprise. Or a startup that they got when they were, 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 for traditional enterprises, where can you win? And even being as narrow as possible. We closed a lot of car dealerships, very large Fortune 500 car dealership companies. That's one where let's just keep taking them down as an example.

Brett:

How did you figure that out?

Lindsey:

You need a really data-driven RevOps and sales team. We got very, very granular using a lot of the tools out there using AI, but just people who are really focused and inquisitive. And then we started doing very quick iterations of if 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 you have referenceable customers, you're seeing good takedown strategy.

Brett:

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 prey and you're trying to find these niches or you need to find a more efficient path to start to stack the niches on top of one another?

Lindsey:

I would look at where are you performing well in the mid-market? Do a really deep vertical analysis, talk to customers. Know 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 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 buyers and it's different, yeah.

Brett:

When you think about 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?

Lindsey:

I mean, the way that I think things work best for anything like this, not just enterprise, is to have dedicated people trying and moving quickly and sharing information together. I don't think it needs... So I wouldn't put it totally embedded. Let's put this through the exact same process for the rest of the company, but it shouldn't be 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 an entire product stack." But you need one person who is embedded with the team and is 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. And that could just be specific name individuals. In marketing, you're the person in product. They don't have to be completely separated.

Brett:

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?

Lindsey:

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 we got to figure out how to do that. Because 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 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.

Brett:

Do you think it's clear that the AEs need to understand enterprise and that being an enterprise AE is different than being an SMB AE 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?

Lindsey:

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. 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 SMB commercially up into enterprise.

But 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, we are like, "That's a no-go for us moving forward." So everyone needs to know grown up through, you make your own pipeline, which is hard to teach that if you've not grinded it out on the phones or doing outbound without a fresh, warm book.

Brett:

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. What's going on with 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?

Lindsey:

Yeah. I mean, I also... Especially post-COVID, 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. I think that the crux of it is a sale, it's a leap of trust, and especially at that enterprise level, you're making a big decision. Often as a buyer, your career, this is a big strategic thing you're recommending internally, you don't want to take risk on behalf of the company, and so a lot of that comes down to the trust you're making in the individuals. Humans are humans. I don't think anytime soon in enterprise sales specifically, that's going to be replaced on the AI or on the agentic side. But it's that human-to-human contact is 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 I'm sure you get invited to events, you get invited to a lot of events. Most of them... I've got children at home. There's opportunity cost of going to an event if 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, not just another basketball game. It could be that. But we've done Houston Rodeo or Devil Wears Prada Premier in New York, just something that's different or very strong thought leadership that's going to help you in your job. And so it can't just be go to the same event, it's got to be targeted and high value.

And then lastly, 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.

Brett:

But if you think about going from CRO to COO in the context of Checkr, what was by far the hardest parts of that?

Lindsey:

The 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 myselves into other people's business who were not on my team. So let's look at the supply chain, which is owned by another function at that time. How can we improve that? Or our recruiting velocity, our hiring approach, is this working well? Hey, let me partner with you on that. Looking at our metrics with our CFO at the time, "Hey, I don't think we are 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 no, those are my peers objectively, but I had to lean in and push them.

And then also working with Daniel, 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 feedback both ways obviously. And then figuring out the right balance of, hey, running the... I do our company business reviews and he's up back more, but making sure that 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. And he and I are always working through that and finding the right balance to make sure we're on the same page.

Brett:

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? One would imagine, "Why are you involved in what I'm doing here?" Or very easy to get defensive, very easy to get, territorial. Very easy for that person to then say, "Well, let's talk about your part of the..." Or all of the interpersonal things.

Lindsey:

I think it starts with trust and building that trust with each other. I think 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 we do offsites together and 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. So that's a big part of it where you have the license to push each other. I think the second is that I had to get out of my own way and this is my job. I debate, I push, but I like harmony. I had to tell people explicitly what I was doing, like, "Hey, this is my job as COO. I want to partner with you. 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 when he came, is like, "The sales collateral's not very good." He's a very strong enterprise-focused product leader, and, "You're right, let's go improve this together." So it should go both ways. I think that from a mental framing as an executive in this role, it's that this is what is expected of me and we're not doing well if go-to-market's functioning well or operations is functioning well, but there's issues over here.

Brett:

This builds on what you were saying a second ago about building cadence and systems and process as 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 doing the work. 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 want to 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 what's your general philosophy on the role of process and standardization while also allowing for judgment, agility, pushing decisions to the edges of the company, the tension and those two things?

Lindsey:

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... The more process you have to take things up the chain, so to speak, the more people are spending on internal stuff versus getting work done. 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 Checkr, 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 very practical things. But I think first of all, Daniel and I sat down a couple of years ago and said, "Okay, what are the decisions that you need to make? Let's just document it."

Brett:

So what are some examples of that?

Lindsey:

Deals above a certain size or any major brand campaign, not a demand gen, but any major brand decision. Any product monetization that's going in a completely... We're a consumptive model. Changing a product to SaaS is an example. Our CEO cares about swag. So it's like what we put out there, people are wearing. That's an exception he gets. That's not a big one. And we keep looking at it and saying, "Where can we push that down to the next layer, the next layer?" So there's that. I tend to think there's the whole rapid racy... I think sometimes it's just too much process, but what we've rolled out is two things. One, for every initiative or anything happening, who's the DRI, directly responsible individual, and that's just in our lexicon, because we saw a lot of swirl happening around unsure who was taking the next step to who owns something and codifying who is the decision maker, because we saw naturally everything was just flowing up 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 say like, "Oh, wow. I'm the decision maker on a lot of things. Push it down." 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 one big thing we put in place in terms of mechanism to flow decisions.

Brett:

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?

Lindsey:

Key DRI, how are we thinking about major product roadmap trade-offs? 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 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 exec 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 how many sales reps should we have going to next year? We're going through that decision right now. And I think that if you're aligning incentives of everyone... People are getting paid on the things that are read by the company. If their goals are really thoughtfully aligned, then a lot of those things are... People are going to make the right decision.

Big M&A, this 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. When I have a new hire, a new leader, I'm investing more time upfront like, "Here's how I would make a decision. Let's look at this one together and then after the next one, you go with it." So there's coaching involved as well.

Brett:

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, it's oftentimes very hard to get it right?

Lindsey:

I think hiring is one of the hardest things where, especially executive hiring, or... People just are really good interviewers at that stage in their career, and the stakes are high, 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 in 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. Nothing worse than that is no decision. I'm working on it then with my team as well. If I trust your process of making a decision, then hopefully you'll be right and 10 out of 10 you probably will, but there will be some misses and I might've had the same outcome.

Brett:

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 have a feel for the business or there's this risk that you turn into a Dilbert exec that's so separate from everything and so you have to stay close to the metal?

Lindsey:

Absolutely, and I think it's easier than ever now. Staying close to your team, but then the broader organization. Even in our office, Daniel and I sit together in one area and then I have a separate place, I just sit with the team in the sales floor or whatever, just to hear through osmosis what's happening, talking to people in the hallway, et cetera. But now with AI... We're heavy Slack users, we have a channel for every single customer, every single deal. We're very structured about this. I can regularly keep pulse of everything. Getting that felt sense of intuition and sentiment is what's important to me. I'm very data-driven, but an intuitive decision maker layering the data into it. And so if you're not getting that, if you don't have a process by which 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 sitting over here 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 let's make sure we're getting their input. I've seen this in both ways. I've been in an organization where people are making decisions with completely lacking context.

Brett:

I would think one of the things you spent some time working on in your role is 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 comp. 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 things like that as you try to figure out how to incent and align many, many, many, many people?

Lindsey:

I mean, the biggest experience I've had in this and learnings has been in the sales compensation and moving from a SaaS model to consumptive. So at Google, we were in G Suite, a SaaS. You book a deal, 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, so it's like how much the customer's going to spend, how much do you think they're going to spend. In reality, we don't collect revenue until based on how many checks they're running. And so 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 if you're comped on this, your pay is aligning with value to the customer, which is then aligning with revenue to Checkr. And we've had to tweak some things here and there, like what's the sort of leading thing we can give them when the deal is closed? But it's been a game changer in terms of the way 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 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 someone too much scope, then they're not getting incented on anything. If I'm comping my sales leader on total revenue for the company, that's not high leverage for me. And then just giving them the guardrails so that we don't go out of bounds. For a sales incentive comp, if you do all of those things and then you can set up to have a winning sales organization, then it's like these decisions are easy. Should we add more reps? How do we treat this one deal? It just makes everything easier than if you have the shadow approach that's not aligned with your company's success. And oftentimes for founders or for leaders, a sales leader will come in and say, "No, no, no, we need to do it this way," and no, you don't. Really think first principles.

Brett:

What other reflections do you have about variable comp for sales? Because I feel like you have a bunch of 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?

Lindsey:

Yeah. 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. Sometimes I get asked, "Why do salespeople make so much?" I'm like, "You want to go take a quota and have your salary cut in half? Have at it."

Brett:

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."

Lindsey:

I think the hard thing there, which is I think... Love any thoughts you have. But measuring the effectiveness of-

Brett:

Inputs and outputs.

Lindsey:

Yeah, it's hard. And we talk about this all the time. How do you know you have a high-functioning org? Is it the number of things they ship? Is it the quality? 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 the input that's made, the output that they're driving, and that it's a non-negotiable, very clear scorecard, it works well. There's MBO plans where you're... I've done those for certain roles where it's five categories and you're rated on them at the end. It's just a ton of overhead. It doesn't drive as much the same behavior. And sales success breeds people staying. An enterprise AE is 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 is I think you can get really stingy and be like, oh, we have accelerators. If you're making above your quota, it's going to go to accelerator mode. We've had times where there's caps on that or we're stingy on that. It's like that's not the right move. 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. This math works. I think the highest-performing AE should make a lot more than a lot of people in the company.

Brett:

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. Because a superstar theoretically... Maybe the average PM should be comped at X, but maybe the superstar PM should make 3X or whatever. And yeah, you have career ladders and this and that, but it doesn't work the same way as sellers.

Lindsey:

And I think that's where things are moving more and more is differentiating, paying more for performance across all roles. And especially with leveraging AI, you can get 10X more out of a certain amazing engineer than an average one.

Brett:

In working across so many sellers, what's your working theory if you take in any team that you 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.

Lindsey:

People have the misconception about sellers. They're like, "Oh, it's the most outgoing guy over there that's going to be the bestsellers."

Brett:

A lot of them are very introverted, I find. They have to turn it on and they need to re-energize.

Lindsey:

It's probably two ingredients for me. I mean, building trust with customers, being able to do that is a gift or it's 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 thinking through what are all the moves I'm going to make? How do I structure those? How do I rally all the resources? It's a team sport. And I do that in a thoughtful... Like a captain of a team. And I think reps who are good-

Brett:

People that are IC reps, they have to think about the world that way.

Lindsey:

They have to think about their world that way, and they're just exceptional at 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, 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 thinking through how to get into the customer and bring all the resources around them.

Brett:

Going back to 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? 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 the CRO hat keeps calling you back because you're really good at that thing.

Lindsey:

Yeah. No, absolutely. And that's the ongoing push that I'm looking at. Where am I spending my time working with Daniel on what are the next big strategic things we need to be thinking about? One of those, for example, is a company we have acquired recently or a year ago at this point, but integrating that across the whole company and accelerating that business. So that's a go-to-market angle, but 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 have exceptional leaders.

Brett:

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.

Lindsey:

Yeah. I mean, I think that I've had this so many times throughout my career. I think the first times, I mean, I took over sales engineering at one point in Google for my world, my segment, and I had not done that. 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. Can I add value?" And I think it's just about as you get more and more senior, your role as a leader is to help remove obstacles, help think through strategy, help think through 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 where I spike, where 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 I think that you'll flag to me... 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 test, but that the trust is there, that they know that I'm going through that process with them and asking questions to make it better.

Brett:

So when you look across 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:

There's the company-wide and then my team. For the company, at the C-staff 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 one time out of several that it's 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 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 supports that first team mentality of this is your first team, it's not your function. I think it's a key part of how we operate and helps us function very well.

Brett:

And it's 30 minutes or an hours?

Lindsey:

30 minutes. 30 minutes.

Brett:

And there's no agenda, you just show up and talk about whatever?

Lindsey:

Yep. There was 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 conducive to building that trust I talked about earlier. Every two weeks we do a review with all of our top 20 leaders of the entire business, and so that is a... We're a document culture, which is we do the silent read, comment and discuss after, and that review of that document is the cadence by which we're reviewing.

Brett:

And the document's like a business review?

Lindsey:

It'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 the revenue, the forecast of the revenue overall as a company. That is critical, and there's cascades up to that with each function. I do a revenue business review every two weeks.

Brett:

But on that review, what is then happening? So everybody sits down and reads it, and then what's the median used for?

Lindsey:

It's a kind of intake of information. So everyone's clear on what's happening across, and then we discuss, people flag, "Hey, I want to discuss this." And so there's five to 10 topics or any goal that's read or off-track, we'll discuss as well. And we'll go through, problem solve live, hey, if there's an issue. An engineering issue over here, or hey, there's a customer situation here, what do we need to do? And 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 certain goals are quite off-track, we will do a separate deep dive one hour where we'll go into that and we do those monthly as well.

Brett:

And then you were saying you have every other week is a revenue-

Lindsey:

We have a revenue business review just on the revenue organization. Twice a year we bring our top 80 leaders together in person, 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 the director of demand gen or the director of platform engineering. They are driving the company and we're at that stage where we're not big enough to have completely federated approach. 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 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.

Brett:

And so throughout the year, you disseminate through those 80 people?

Lindsey:

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

Brett:

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?

Lindsey:

You're auto-added, just to make it very straightforward.

Brett:

And then what's the difference between that group and the top 20 people?

Lindsey:

The top 20 is VP, and that top 20, we're meeting in person as well. Two additional times per year, just that group, usually offsite. And that's a mix of setting the strategic goals for the year. It is 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. So we do this when 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 as everyone's executing, that alignment is really important.

Brett:

Do you think if you were to be a CRO again, it would be marginally helpful that you had this role or it would be a big deal in terms of your overall effectiveness?

Lindsey:

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

Brett:

On the data piece, where have you found that data has led you in the wrong direction or had massed something that you could only know qualitatively or there are these pitfalls if you get too focused on managing through a dashboard?

Lindsey:

There's 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. People are seeing more and more... Inadvertently hiring North Koreans into their company and wondering what line of code did this person change? Having someone that's stolen an SSN and is on multiple platforms. So all of these things, we kind of knew here and there there were issues, but as I started to talk to customer A, to customer B, our chief product officer and our sales team hearing more and more, that just gleaned from connecting dots, and that has formed a really big strategic investment for us and 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 may be doing this for free, or maybe this is a very low identity verification is a low ASP product, we don't need to spend a ton of focus here, but it's incredibly strategic in the bigger picture. So that's one example where you can't just be looking at data, you have to supplement that with as many customer conversations as you can. And for reps who are having those calls every day, they're not in the right role to be able to share that information up or to push for a strategic direction. It has to come from you.

Brett:

And 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:

I think that's the ultimate goal you're trying to get. I think 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 from obviously the teams, and we've built a whole customer LLM that's got all the knowledge on all the customer support calls and all the sales calls and whatnot, but going direct to the source is, I see the highest value. And also having that empathy ongoing is really important. And that's actually 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, Lindsey's going to be on the call. What's the agenda? Does 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, don't bother."

Brett:

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. Any reflections on that process of trying to articulate the business in something much more numerical?

Lindsey:

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

Brett:

Yeah. It feels like if you have a consumption-based model with incredible NRR, you run the risk of actually underemphasizing net new business because you can hit these incredible 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:

Yeah. No, I'm a big big proponent 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 this just is what's the driver. It's just as bad as not growing in some ways because you don't have control over it.

Brett:

It's like the classic thing, 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 were unable to predict.

Lindsey:

I mean, I'd rather exceed plan, but if you don't know why, I will lose trust in you. You better know why you're exceeding plan. Yeah, I think that the metrics... One thing that we do at Checkr is there's obviously the financial metrics, the revenue, new revenue, margin, EBITDA, which govern our financial plan, but I mentioned earlier, we have strategic goals we set. We spend a lot of time in Q4 every year 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 percentage of revenue from this new product area that we've got product market fit, we want to scale it up, for example. Or it could be strategic investment in we're building a people data graph, which is just work outside. This is not directly monetizable in the short-term, but it's strategic long-term.

So those type of things, having those set, communicated to the company, and then everyone knows when you're trying to make trade-offs, you're bias 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 10 things that we've got metrics on. So those are pretty clear. And then beyond that, there's a proliferation of metrics, but having key owners of you own this and all the things cascading up to it so that you're having distinct accountability. I think more frustrating to me is there's a metric and 12 people think they own it or that means 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 missed than to get 130% of the goal because that means you weren't thinking big enough.

Brett:

But I feel like one of the downsides of setting particularly ambitious goals is 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, and if you do the classic OKR thing where you want to get 70 or 80%, 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 or do you-

Lindsey:

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 the sales team quota overall, that should be ones where we want to hit that within 5%. Strategic stretch goals and initiatives, we label them such like, "Hey, 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 where you have to rethink the way your team works. You have to 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:

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.

Lindsey:

And it's really hard for someone in seat to think about completely rethinking. And so you have to force them to.

Brett:

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 cool demos and all this other stuff, but in production, in the way the team is running and working, it has made a profound impact on what you all are doing.

Lindsey:

Maybe starting within my organization, but in operations, this is all of our supply chain polling data, customer support, candidate support disputes as part of FICRA processes. All 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 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, improve three X in terms of CSAT, and we've been able to substantially scale without adding more headcount. And the cost per revenue dollar has gone down dramatically.

Brett:

And in a given day or a given week, how does that impact the business?

Lindsey:

It allows us to know where to invest our roadmap or even what customers might be showing signals of growth opportunity or distress in some way because, hey, there's these customer support tickets or this international product is picked on. That's one where, hey, we're seeing this come up on several calls for this country. There's maybe an issue there where we need to prioritize this more quickly to win more customers or prevent churn of these 10 accounts or something like that. So it's like a real-time signal so that we're not in this annual planning process and quarterly, but real-time capturing opportunities for growth or turn reduction. So that's great.

And then also the other part is just cost avoidance on the agentic side. On the sales side, we've had AI SDRs is basic that happened a while ago. We've done... Building this with a partner, but an entire orchestration layer for outbound. That was an area where it's like to do this well, reps have 20 different systems they're having to go into to do all the things. And so we built 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. It obviously takes investment to continue to improve, but that's a big bet we're making.

Brett:

And has that shown tremendous promise?

Lindsey:

It's shown promise. Yeah. Yeah, absolutely. And I mean, our outbound pipeline is a percentage of total pipeline is continuing to grow. And another area we're early in, but account-based marketing, it tends to be very manual. Can we 100X that in H2 through this and other tooling we're stitching together? On the engineering side as well, over 8% of our code is now written with generative AI, so that's another area. So there's very fundamental in-production use cases. And then as I mentioned, we've got really blue sky goals for H2. If we get 40% there, they'll be very meaningful. To do this well, I mean, that's the hard part. We pushed AI tools to the entire company pretty early. Everyone has a Claude license, a Lovable license, and we did hack days, non-engineering hack days to drive this. And so it's like, first, everyone's just building stuff for their own productivity, which is great, but costs money and it's maybe making you marginally more efficient.

And then the push is to move people to build an app that is business impact, like hey, a Customer 360 skill in Claude or agent that will help us actually have better insight into this customer. Everyone's building the same thing. And so then it's getting the shared agents that everyone's using the same one, someone centrally manages it. And then eventually workflows and systems is where we need to move to because we don't want AI for AI's sake, but give me the signals that a customer is challenged, send that to the CSM immediately to activate this outreach sequence. 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 company's all the rage, but we're investing substantially in it.

Brett:

And so have you found that 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? 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...

Lindsey:

We're moving toward more centralization, but it's important that we get everyone up to a higher level of AI fluency. And so we've defined what those levels are and are assessing people on the moving up. But we don't need every single ops agent building an app. They need to be handling tickets and we don't necessarily need every SDR to be building the next app for that. 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 now we're figuring out how to scale. So we're going through that journey right now.

Brett:

If someone is a bit earlier in their career and they are thinking about where do they want to take their career and they're 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? 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?

Lindsey:

If you're not in a revenue sales track... A lot of RevOps folks I meet want to be COO. I think you got to run revenue sales teams specifically at some point. 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 motivating and driving and running a sales organization. I think that it's a bigger leap to go from support function to COO owning revenue if you've never done it. So I've seen people who go from that to being an AE, and then that combination is huge because you know the operational part, you've done sales or sales leadership 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 there are a lot of more and more sales leaders now have that acumen and ability, but it has to be intentional, understanding if closest to is 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 a sales leader is so narrowly focused on the quota, the number, and doesn't spend time getting that insight and learning. And that I think could be a blocker to becoming a COO at some point.

Brett:

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 grow into a COO other than just hard work and intelligence?

Lindsey:

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 was the combination that Daniel valued of like, "Hey, I know that I could trust that Lindsey's going to hold 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 and building trust. Low ego is really important to us at Checkr. 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 Checkr successful. I want to make Daniel successful. I like that partnership and trust is really important.

Brett:

Right. Great place to end. Thank you so much.

Lindsey:

Yeah, thank you.