“You have to play the game as it’s on the board.”
What does a corp dev team actually look for when they’re evaluating your startup? And what’s it like on the other side of the table when you’re the founder getting acquired?
We brought together two perspectives that rarely share a stage: Scott Haylon, Senior Director of Corporate Development at Datadog (who’s completed over a dozen acquisitions), alongside two founders who’ve been through it—Kevin Hu, co-founder of Metaplane (acquired by Datadog in 2025), and Jeremy Neuberger, co-founding CTO of Finmark (acquired by Bill.com in 2022).
What we ended up drawing out was a candid look at the signals acquirers use, the things that kill deals, and what founders wish they’d known before going through the process.
TL;DR: The best acquisitions start as relationships, not transactions. Build for your customers (not your potential acquirer). Come with a point of view on how you fit. And above all: don’t hide the ugly stuff—trust is everything.
This virtual event was presented by Bill.com

BILL (NYSE: BILL) is a leader in financial automation software for small and midsize businesses (SMBs). We are dedicated to automating the future of finance so businesses can thrive. Hundreds of thousands of businesses trust BILL solutions to manage financial workflows, including payables, receivables, and spend and expense management.
Welcome, everyone. Super excited to have everyone joining. We’re just gonna let some folks roll in here for a few seconds. We wanna get you in and out on time. We know everyone’s busy, and we’re super excited to have you here. We have an amazing topic today. This is really something that you don’t see a lot or at least I don’t see a lot, and that’s why I was so excited to to to bring this to you, and the team was so excited to bring this to you today. But we’re gonna show you what really happens inside an acquisition, and it’s gonna be from both sides of the table. So we have the founder side represented, so folks who have had their companies acquired. And then we have the corporate development side, so the teams within these bigger companies who are going out and doing these actual these acquisitions. And I’m just I’m super excited about it because it’s something that doesn’t get a lot of airtime, at least in this way with this combination of folks. And so let’s quickly dive in with some of the some of the details. First of all, I just wanted to mention, if you’re not familiar with Venture five, we’re the venture capital industry hub. We’re spanning three different arms. Our first arm is media. We’re creating content, such as this about venture that empowers. We’re also improving access to capital for founders and funders through what we call catalyst, and then we build products and services that solve real problems for the venture ecosystem, and that’s our studio. And you can go to venture five dot com for all of that and more. Also wanna give a huge thanks to bill dot com for helping us bring this to you today. We have Jeremy on our panel from bill dot com. He’s a founder who exited to bill dot com, which is super cool. And, Jeremy, do you wanna just talk about bill dot com? Yeah. Absolutely. And thank you, John. I mean, here at bill, we empower small businesses and accountants, with complete visibility into your payables, your receivables, your spend, your expense, so you can really take control of your financial operations and run your business with confidence. The latest is, you know, delete busy. We spend so much time on just getting the finance done and making that as simple as we can. Awesome. Thanks, Jeremy. And I think myself as well as a lot of folks who are watching this, have probably logged in to Bill dot com either to to issue a bill or to pay a bill. So it’s really cool to be working with with you all on this. Manali, if we could switch to the next slide. Let’s do some intros. Jeremy, while we’re here, why don’t you give a little bit of background about how you came to Bill, and and, you know, what your role is there today after the acquisition? Yeah. No. Absolutely. So, I was the cofounding CTO of Finmark. We made it simple for small businesses and startups to forecast their future, test drive your business, make sure you know what you’re doing with your money, and simplify things between you and your investors. We were acquired back in November of twenty twenty two. Came into Bill, senior director of engineering. Currently over integrations, cash flow management, and, you know, taking a a big step into AI agentic workflows for our customers. Awesome. And let’s go down the line here, Scott. Sure. Yeah. So, I’m Scott. I’ve been, Datadog, ten years. Started the corporate development function here about eight years ago. Actually came to Datadog, through an acquisition. They Datadog’s first acquisition was a, startup I worked at called Mortar Data, brought me in back into the fold here at Datadog. So, yeah, seeing the whole spectrum from when we were doing our first early acquisitions to, you know, what we do now as a public company, inquiring awesome companies like like Metaplane. Fantastic. Kevin, that’s your cue. And while Scott is an OG, I’ve been at Datadog for around eight months since the Metaplane acquisition. I was the cofounder and CEO. We started the company in June of twenty nineteen. We would call ourselves the Datadog for data, but it turns out that the Datadog for data is just Datadog, and I lead the data observability product at Datadog now. Awesome. Fantastic. I’ll I’ll share a little bit of, like, Datadog personal history at least that, you know, I I was not at Datadog, but I remember meeting Scott when he was at Mortar Data. The the one of the founder’s name was was Kay Young. And, yeah, I remember meeting Scott. It was, like, about ten plus years ago, so it’s been really cool to, like, reconnect and and work on this. But I also remember sitting in a restaurant in Manhattan and looking over and seeing Olivier, who’s the CEO of Datadog at lunch with Kay Young, one five fine day. And little did I know that a few months later that MortarData would become part of Datadog. So kind of a cool full circle moment and really really excited to be here. So, yeah, why don’t we why don’t we get started? You know, I think, Kevin, for you, in terms of this acquisition, you’re less than a year in. How did it sort of go down? I know it’s probably a sort of a long process, but, you know, maybe just, like, the high level of sort of how everything happened would be really interesting to to understand at a at a high level. Well, it started, like, all good relationships with someone sliding into someone else’s DM as opposed. If we really go back that we someone from Datadog Corp Dev reached out to us at Metaplane, and we met some folks on the product team who were interested in data at the time. I think Scott can speak more about, like, that team and the product and how that’s evolved at Datadog. But we had first contact, you know, shared what we’re working on, sharing our demo. We kept in touch about a year later when we were raising our series a. We were talking with Datadog as well. We didn’t quite join forces at that point. But about one year after that, the current acquisition process got started in earnest. And, you know, we we brought it to the finish line in April, like, this past April. So on the whole, the process, you know, we were in talks to make an acquisition happen for maybe about two years, which is longer than the acquisition has actually been. Okay. And, Scott, from your perspective, how how do you how do you sort of see the story? You know, what what what happened prior to that that outreach from your team? What what sort of caused that? What spurred that? Yeah. So there was there was the initial outreach was wasn’t I wasn’t involved in that conversation, but the subsequent one around the time they raised their series a, we met them sort of in as they were having those conversations. And, like, candidly, we made a really hard push to try to acquire the company then. Thought there was a really great fit with Kevin and his team and what we’re trying to do, but, you know, couldn’t couldn’t quite, get things to align at that time. And then, just stayed in touch, over the course of the the next, year and year and a half or so. It worked out that Kevin’s, now wife, lived around the court. His fur family grew up. It was right around the corner from me. So we would see each other in Boston, and I would come to New York, and I would make a chance to see Kevin. And so we just, I think there were a lot we always got along really well and thought you know, hope that there were be an opportunity for stars to align in the future. And and, eventually, Kevin was ready, and so we were able to kinda reengage at that time. Nice. And, Jeremy, for you and your processes, you know, cofounder of Finmark, was it sort of like a kind of an outbound from Bill, or how did that all sort of start to take shape for you? And what was that, like, timeline from, like, first contact to, hey. We’re acquired. Yeah. You know, it’s a it’s an interesting answer, because as the CTO, you know, my cofounder and CEO was doing a lot more of the outbound. But, you know, we were actually just looking to raise a series a. Right? We had been running for a couple years at that point. Our customer numbers were going up. We were getting closer to metrics for a good series a. And I just get a note one day from my, my cofounder just like, hey. Have a meeting coming up with Bill. You know, could be a big, you know, business opportunity for us. You know, our customer segments align. Let’s really make a splash. And I’m like, great. I get my engineers on. I’m like, you know those things on the backlog that we’ve really been wanting to do, to, you know, really excite people? We have two weeks. Let’s make it happen. And, you know, took a call, and I wanna say it was within, you know, maybe two, three months. There was a letter of an intent, and, it was a very quick process from there. And quick, not because of a lack of work, but, you know, we wanted to push quickly to to close it out as opposed to raising the series a. So, you know, start to finish, it was, I think, six months from my vantage point. Okay. Interesting. So some some commonality there around that series a, you know, sort of time frame. Scott, why why is that? Do have you seen that across other deals that you’ve done at Datadog, or how does the fundraising dynamic play into the the m and a dynamic? Yeah. I mean, I think every founder who, you know, looks at raising another round, has to think about, okay. Well, what am I what kind of outcome am I signing up for? What sort of, dilution am I gonna take in this next round? And, you know, how does that compare to you know, if I have an acquirer that I’m potentially excited about selling the company now. You know, I’m I’m gonna take on this additional dilution. I’m sort of promising or at least, going in with an understanding that these new investors have an expectation that we’re gonna, you know, return make a a big return on their money that’s, of course, you know, raise it up higher valuation in in the case of a, you know, a new series a, series b, whatever it is. So I do have a lot of conversations with founders right at that time where they’re saying, hey. Look. We’re you know, we may go down this path, but wanna explore both in parallel. And, you know, in some cases, they decide that they’re ready to to double down and wanna see see, you know, as Kevin put the time or another card turnover. And in some cases, they feel like, hey. You know, now is the time. I think everything’s are coming together, and we’re excited about joining Datadog and and doing what we can do here, together. And they decided to go down that path. But, sometimes you don’t actually know until you pursue both, you know, fairly seriously and and kinda can see both options laid out in front of you. Kevin, how do you sort of, it’s funny. Like, you think about start up pitching. You’re you’re pitching to rage your seed round. Like, I imagine you’re probably pitching, like, this big vision. Right? We’re gonna build this multibillion dollar company. But the reality for a lot of founders is, like, well, you know, if if there is an exit, right, it’s it’s usually via m and a. So how do you how do you kinda manage your investors’ expectations in terms of, like, that fundraising piece? And then, well, by the way, you know, Datadog came, you know, inbound to us. We’ve been getting to know them for a year or two. Maybe we should talk about this kind of in parallel. So how, yeah, how did you navigate that, and how did you work with your board and, like, main investors on that? Well, there’s there’s two tracks to answer that question. I think one track unifies the two, which is your fiduciary responsibility, which is, you know, founders. Everyone is so different. Every opportunity is different, but we get in the game to make a big impact. Right? But the problem is that you have to play the game as it’s on the board. And sometimes opportunities close, sometimes they open up. And if it turns out that the the chance of your startup going the distance, which is what everyone in this room wants, everyone wants their for their portfolio companies, if the probability of that is going down and the probability of another exit is going up, I mean, you kind of owe it to yourself and your investors, I would say, to have conversations with potential acquirers given that it doesn’t distract you too much. Right? So the way that, at least, we framed it is these conversations, right, people are reaching out to us. We don’t wanna close the book on them even though some people do recommend that. Right? We wanna kind of, like, keep all of our options open so that we are, like, playing the game on the field today. On the personal perspective too, I would say, and I’m curious, Jeremy, how you all navigated this is that, you know, some people are, you know, burn the boats kind of founders. Like, you know, I this is gonna be a hundred billion dollar IPO not talking to anyone. Personally, we are more in the camp of, like, let’s be realistic. This is not our only time. Like, this is not our only start off in us. Right? Gotta make the the best choices, and that means having choices to start, and that means having these relationships at all. But, yeah, I’m curious here. I mean, how y’all balance that. Yeah. Well, you know, what’s interesting is, you know, when we started talking to Bill, you know, initially, like I said, potentially just partnering, providing our product to their to their companies and, you know, creating an integration, those types of things. You know, I’m really just looking at the customers. Right? Like, what is this change going to mean for our customers, and and what is this going to mean for our product moving forward? What kind of opportunities do we have together? Now when it changed from, you know, potentially, partnering in some way to potentially an acquisition, you know, my first thought was our employees, honestly. It was, you know, we pulled in people that we had all worked with before. You know, we had grabbed people from our network that we trusted, that we knew, you know, would work hard for us. We would work hard for them. And the first thought was, you know, is this a good place to land for our employees? Right? We can either, you know, go ahead and finish off the series a. We’re gonna have plenty of runway. We can hire more. You know, we can really, you know, shape that hockey stick. What’s that gonna look like over the next, you know, two years? Now if we land the plane and this is where we’re landing, what is that going to mean for the product we’ve built? What’s it gonna mean for the employees? What is it gonna mean for our customers? And, you know, everything just matched to the point where, you know, it seemed like an obvious answer. You know, there’s so much so much synergy in kind of the market that we were hitting on the problems we were solving to where for the customers, like, this is an amazing win for customers. For the product, like, we now have more eyes than we can imagine because of the scale of bill. So for the product, it’s amazing. For our employees, you know, startups cannot do for their employees what larger companies can do for their employees. And when you join a small startup, you you know that. And you’re looking at the equity as, okay. Well, this is why this is okay. Right? And so you just put all those things together, and it’s like values align, customers align, you know, the product’s gonna be beneficial, and I think my employees are gonna land in a place that fosters the same culture that I’m looking for. Like, this is great. Everybody wins. Investors are happy. Customers are happy. Employees are happy. Let’s do it. Scott, how how do you or how can a founder sort of accelerate to getting to that that happy place where, you know, Datadog or someone, you know, a large acquirer is taking, like, a real close look? Obviously, that that series a, you know, raise, maybe that’s kind of an event that can can cause some urgency. Are there other things that you’ve seen that either founders can do or just market dynamics that might all of a sudden mean, hey. You know, we we gotta move fast in terms of there’s a company or maybe a few companies you’re looking at in a certain space where, like, we have to go and, like, we have to acquire now. You know, we’re we we we’re pretty deliberate about looking at new areas constantly. And, of course, some of those end up in us deciding it it doesn’t make sense. But once we get down the path of, hey. We wanna do something here. We you know, we’ve had a lot of, success fortunately with with m and a when we decide to get into these new areas. That is where we usually start from. It’s it’s through our team. So, you know, once we get to that level of conviction, then it’s a a exercise of trying to find, you know, the right company that will fit well with Datadog specifically. You know, think similarly what we do about products that we think culturally will align well. I think they’re motivated to build something great as part of this this next chapter. So, you know, from there, what’s getting us excited is the interactions with the team. Like, in in some cases, we have, like, a a longer lens on things. So with Kevin having interacted previously, we got to see the delta between, you know, our first interaction the demo we saw then, and the you know, trying the product then and what we saw, you know, a year or so later and had a really good lens into the product velocity. So that was really another thing that got us excited. So it’s more just about we we try to move pretty darn fast in general towards those things that we find most interesting, but I think, you know, the interactions with the team and, you know, the alignment on how we feel about what we wanna do together. And then in, you know, in Kevin’s case, it wasn’t just a single point in time, but we had, you know, sort of a ability to track the progress. That altogether made us you know, made it much easier to get comfortable to have to kind of spend a lot of time thinking about, hey. Does this make sense or not? Is this the right company for us or not? We had a lot of data points to go off of at that point. And how can I even get on your shortlist? Right? So let’s say, you know, if there’s some product strategy around, I’m gonna make something up, cybersecurity. So let’s say that lands in your lap. Like, how do you actually build the shortlist of these are the companies that are interesting to go after in that space for whatever reason versus, you know, maybe these other ones aren’t? Like, what what’s the process that you go through to to come up with that list? Because, obviously, there’s so many companies in every different space. Like, how do you decide where to focus? Yeah. I mean, let’s get to, you know, specific areas. Like, we’ll use data observability example because Kevin’s company. Like, there are only so many companies, there. And, you know, it’s not a short list, but it’s, no. They’re findable. Alright? So, you know, you try to go through every angle you can. You know, a lot of it is reading about a lot about the industry. A lot of it is, you know, knowing the relevant conferences. So, like, in in, you know, Kevin’s company, of course, they’re going to, the conferences for companies like Snowflake and Itabricks and and the like. So you’re starting to see folks pop up there. You know, you can you can find these companies in a bunch of different ways pretty quickly, actually. I I I find that that’s a relatively easy part. Occasionally, you you find a lesser known one that’s just, you know, under the radar. But but in, you know, Kevin’s case, he wasn’t exactly quiet on, talking about his company. And, so they would come up a bunch. I think also pitching themselves as Datadog for data observability also, you know, made that very easy for VCs that we would chat with to mention the company that and VCs, by way, can also be a great source of of information about interesting companies that may or may not have have gotten to our radar. So, yeah, when I when I find an area I’m interested in, of course, I’m doing all the usual online stuff. I have regular catch ups with lots of investors, and I’ll I’ll tell them. I’m pretty open about what we’re interested in, and that will generate some some ideas there. Even sometimes from companies that aren’t necessarily squarely doing exactly that thing, but maybe the team has a lot of relevant skills to go build in that area. And then and then but then the most important thing is interacting with those company directly, and so we’ll we’ll reach out cold and and have those conversations. Jeremy, you clearly Finmark made the shortlist for Bill dot com. Right? I don’t know if there are other folks that were talking to you at the same time, but, clearly, you were the the the the winner, if you will. You talked about the the two weeks, right, where your CEO is like, hey. We got this inbound from Bill dot com, and then you go to the Ang team, you’re like, alright. Like, let’s go on, like, a two week sprint and and build some things that are gonna really impress Bill dot com. Take me in that sprint planning or into that, you know, sort of room, if you will. Like, what were the what were the things you were like, we gotta push this out. We gotta get these these features shipped. And why did you pick those in the context of why Bill dot com was was looking to, you know, maybe do a strategic partnership or even ultimately acquire you? Yeah. Absolutely. You know, it was something that my cofounder had said while we were having the conversation. He said, hey. You know, they saw our dashboard. They loved it. You You know, it makes it simple to see what’s going on. And I’m like, dashboard. Okay. Well, what’s shinier than you land on something? Are you wowed immediately? Right? And, you know, we’ve been talking for quite a while. You know, every product has dashboard of some sort. Right? You land somewhere. It’s showing you the most important thing to know right now. But a lot of products, you know, you land on a default dashboard that is, you know, the best the company can do at assuming what you’re going to need. And we’ve been talking for a while about, you know, we need to set up custom dashboards, multiple dashboards so you can set it up for you know, I just want my marketing view. I just want my sales view, or I want my overall view, but I care more about my, about my CAC payback than I care about my current cash runway. Right? So I wanna take charts, and I wanna move them. I wanna resize them. I wanna change what type of visualization it is. I wanna change how it rolls up at a quarterly basis, whatever. And so, you know, I heard, hey. They were really excited about our dashboard. I’m like, well, we can make them much more excited about our dashboard. And so I sat down with the with the team, and I’m like, here’s the thing we’ve been talking about. How long is this gonna take? They’re like, I don’t know. Maybe, you know, depends on how far obviously we go, but I bet you we could have these pieces out tomorrow, these pieces out three days, these pieces out. I’m like, awesome. Let’s stack rank it, just start pumping them out, and, you know, we’ll see where we get in the next two weeks. And, you know, we ended up going much further than we intended in that two weeks. And it was super exciting, but it was taking advantage of the velocity of a start up and just, you know, the unity of of a smaller team knowing exactly, you know, what we’re driving towards, why we’re driving towards that thing, and just executing and getting it out the door. It was it was really exciting. So with the team Kevin, I’d love to know if if you guys have done something similar. You know, you knew you were already talking to Datadog for a while. You know, was there a hard press to, you know, slip a couple things in before before that meeting, or was it, you know, hey. Let’s just show up with what we got. You know, maybe we should have. The the way that but the there were some features that I think had a very similar impact where it like like you said, like, you know, not only is impressive to customers, but really paints the team in the strongest possible light and makes it so that we’re we’re kind of on the same page, our team and then the existing Datadog team. One of those things was monitor recommendations. So at least in the observability space, one of the big questions, as I’m sure you’re familiar with Jeremy, this is great if I know what to monitor, but what do I monitor? That’s a big question in data observability. It’s something that we put a lot of emphasis into that ended up being, you know, something that we talked about in our discussions with the product teams quite a bit. I actually, that’s, like, something that I I is I tell founders a lot is, like, you I wouldn’t necessarily say you have to go build something, although I think that’s obviously the best and highest version of this. But, you know, really have a point of view about what it is that you bring in the company and how things might fit within the new company. And you may be wrong. It’s hard to know everything that’s being discussed inside the walls that hasn’t, you know, come to the point of being public facing yet, but it’s much easier for someone to react to what you have to say and and perhaps maybe even see a path forward that’s slightly different than rely on them to come up with it on their own in the midst of their busy day. So, you know, when Kevin comes in and talks to the leaders and the product areas that, he now works with, it’s so much easier if they can kind of have something to react to that says, okay. Like, we thought about bit about a bunch about where this might fit. You also learn a lot about, the product of this company potentially acquiring and also the founders and how they think through that process. It makes it much easier to think about what’s the joint future look like, which is ultimately where all the value comes. If you have to swing too hard, if you have to think too hard, you’re just creating more you’re you’re leaving more room for friction or misunderstanding about what the possibilities might be. So I I I often recommend to founders, like, put some thought into it. Look at the products that you think are the most likely upsells. Like, your product’s gonna be a new upsell from some existing Datadog customer. You know, what product is it? What are they gonna see in that screen that gets them to go and use this new product? You know, what are the things that might be on their mind? And, you know, what are the things that you have to to help coach through? Like, you know, are there new buyers, new personas that are in play, and how does that factor in? And really spend some time thinking about it. It it actually doesn’t require a tremendous amount of time, but I’m surprised how often people just show up with a generic demo. I think putting that a little bit of thought in there, tailoring the demo, tailoring the the top tracks, maybe having and and sending a note ahead of time with some, hey. I’m not even sure if this is exactly right, but here are few things that I’m thinking about. Happy to expand on further in the the call. That I think that goes a really long way. Scott, how do you internally, when you you’re you’re personally interested in you know, maybe it was Metaplane. What happens, like, after that? Like, you know, how do you actually get something done? Because I imagine on a typical corp dev team, one person can’t just say, like, we’re doing this, and then it just happens. Right? So what’s that, like, buying process, if you will? And and I know Datadog does things a bit differently from a corp dev perspective just in terms of, I think, it’s more, you know, sort of product focused maybe than transaction focused. And so, yeah, how does that work in your world versus, you know, what you’ve seen in other, you know, peers in corp dev? Yeah. We we’ve I’ve got, I think, a pretty unique setup here. So, you know, we to start with, like, the team, when we hire people, we hire people with technical backgrounds, people product people. In almost all cases, they’ve never done m and a before, but they’ve maybe been a CS major that was a PM for a bit. Maybe they got some exposure to finance, but they’re not necessarily trained crypto people. Because what we expect is, like, we’re really actively understanding what these companies do, you know, how they compare versus competitors, what are the key features that we actually want folks to build. We come up with a pretty well informed perspective on that, maybe if not in the initial conversation, quickly thereafter. We also have now three engineers on the team dedicated to corp dev exclusively who are getting into the technical details, setting up a POC for the companies we’re most interested in, really try the product, have a point of view on what might be interesting there, recording demos, and then bringing in some of the subject matter experts from the relevant teams to to come and look. So, you know, from that, you know, usually, the process is something like I have an initial call with the founder. You know, I’ve here long enough to have a point of view on whether it might fit. This the next call is a demo with the relevant product leader. And if the excitement continues from that point, and we’ll have, like, maybe, like, corp dev engineers on the call as well, Then we’re getting into, you know, greater detail on trying the product, having that point of view, you know, that we can develop. And every two weeks, like, we catch up with all the product engineering leaders in a corp dev biweekly, and we’re socializing that opportunity all the way up to the CEO, so that they’re starting to get educated on the company. And we’re kind of collecting all the information, the learnings, the thinking, and sharing that usually ahead of those types of conversations so that everybody’s informed about, you know, what’s exciting, what’s interesting, and then has the opportunity to ask us questions that we can go and, you know, seek out answers to. Jeremy, for you internally, going through the process, we talked about that sprint kind of the features that you were really pushing with the team to get shipped. How did you manage the communication internally? Like, when’s the right time to tell the team, like, hey. Actually, the reason we did all this is because build dot com wants to acquire us. Like or did you tell them upfront? How how did that work for, you know, an an engineering team where, you know, I would just imagine, you know, maybe those folks are not necessarily super familiar with, like, how m and a’s work and have maybe not gone through those processes. Sure. You know, I’m always trying to be mindful of setting the right tone and being transparent as far as I can be without setting the wrong tone. Right? And so, you know, with this situation, you know, there was a potential of just a, you know, a business engagement. Right? Just a a you know, how do we create a partnership of some sort here? And so that’s really where I lean is, you know, Bill has x number of customers. Imagine if our number of customers in our system were to a hundred x. Like, this is the kind of opportunity we’re talking about here. Let’s make this happen. Right? And so there was absolutely that excitement from the team because, you know, the whole team, every customer that signed up, there was a Slack channel. It pinged everybody. Boom. New subscription. Boom. New subscription. I’m like, imagine that channel going off every three seconds. Right? These are the types of opportunities we have here. Let’s really make this happen. But, you know, talking about, hey. This could be a potential m and a play. You know, what kind of anxieties could you be, you know, building in somebody or what kind of you know, imagine if it didn’t end up going that way and you had somebody’s expectations inappropriately set, and then you’re like, oh, yeah. No. It went well, but we’re gonna do this instead. You know, that could feel like they’ve either failed or they missed out on something. And and so, really, it was more, hey. Here’s here’s an opportunity. Yes. There’s another opportunity on the table, but we’ll worry about that later. I I won’t necessarily bring that up at that time. Kevin was nodding violently in agreement while you were saying that, so Kevin might jump in. I think he probably has some strong opinions on this. I think Jeremy said it very well, trying to be as transparent and principled as possible. But knowing that not everyone can be let into the tent all at once. Right? What happens if the tent collapses? You it’s I don’t think there is one right decision, but that everyone’s team is different. Everyone’s relationship with their team is different. I have confidence in that the people here, like, at the point of making the decision, we’ll make the right one. It’s a relationship question, I feel, as much as it is as much as it is a governance ones. And, Scott, so we talked about a lot about how deals get done. Right? We have two founders here who have exited. Those deals clearly got done. What are some things that maybe you wouldn’t know that could just, like, totally derail a deal? Like, maybe things are going great, and then to Kevin’s point, the tent falls in. Like, what makes the tent fall in in a corp dev context? Yeah. It’s it’s usually a couple things. I mean, it’s really anything that we isn’t what you know, the way it was represented. Right? So there’s if we find that we just lack trust in the founders, where they talk about, you know, either business how the business has performed, you know, maybe they’ve hid key information, anything along those lines, anything that feels like deception. Obviously, it’s just you know? Like, in any other human interaction, you wanna make sure you can trust the people you’re gonna be interacting with, going forward. I think it’s especially true in m and a. So, you know, I think Kevin and team were great about, hey. You know, here are the things that you should know that, you know, maybe not not the best possible things, but are just, you know, things you should be aware of. And, you know, it’s much better to know those things up front and then sort of find them out later because most of the stuff does end up surfacing at some point. That’s one. Others just like the interactions with the team. Right? Like, inevitably, some of this stuff can be very tricky to navigate. You know, you’re obviously couldn’t you know, as Kevin did, negotiate on behalf of not just, the company and himself, but the team, and trying to figure out how to make those things work. But, you know, really spend the time to think about, you know, these are people you’re gonna be working with and for. It’s it matters a little bit less than directly in corp dev, of course. Right? But especially when you’re interacting with those product and engineering teams that you’re gonna be part of, really just recognizing that that these are people you’re gonna be working with for for quite a while, and the way you represent yourself in front of them is is being monitored extremely closely. And they’re trying to project out what it’s gonna be like working with you over the next several years, And that can be both on just, you know, interpersonal interactions and, you know, and all that, but also things like, yeah, what do you what’s your motivation? How excited are you about, you know, joining this particular new company? Are you really motivated to continue to work hard over, you know, not just the first six months or a year, but beyond? Those those things all are, you know, being heavily scrutinized, and and I think it’s important to think about how you show up for those conversations. Jeremy, throughout your process with Bill, what were the the places where you kinda got pill pulled in? Obviously, there was the the kind of the the feature stuff that you mentioned. Right? But I imagine there were key points in the process where your cofounder, the CEO, who I think sounds like was kind of leading those discussions, would would pull you in specifically. Like, hey. I need your input on x. What are those kind of situations? And are there any pieces of that where you feel like, hey. Maybe I wish I could have gone a little bit deeper on this piece of it or, hey. We didn’t talk about this other thing, but, you know, ideally, maybe we would have if, you know, we go and start a company together and sell it again. I’m curious if there’s anything in that realm for you that came up. You know, I think as soon as there was a potential, you know, I was pulled into the no. Right? You know, we had a very strong trust circle with the three of us, and and so we were all on all the calls as soon as they got moving after those initial, you know, phone conversations. And, you know, I think where a lot of things fell on me very heavily was obviously, you know, due diligence on tech. Right? Like, what’s your tech stack? How is everything configured? What’s your security position? What’s you know, everything that you would need to know to really understand, am I taking on a an asset or am I taking on a a liability? You know, that was where a lot of my time was spent, you know, coming up with or finding documentation on those aspects. But, also, you know, I was consistently analyzing the behavior of our customers and, you know, all of our data so that we could make more informed decisions on on product direction. So there were a number of times where certain questions were asked that I had it off the top of my head, whereas the others would have to go search for those those questions. And so, you know, I think it came down to my area of responsibility and then just knowing exactly who was, you know, who was taking point on what and who would be the best tool for the job for a specific conversation. Got it. So if you think about you know, Scott has a team. Right? And they’re working on diligence, etcetera. You almost have, like, a similar type of setup internally where there’s each founder in a way is responsible for kind of a certain piece of of the puzzle when it comes to working with a potential acquirer. That’s right. And especially, you know, when you are a very small company, you don’t have the resources to spread around. And so, you know, really being tight on, you know, dividing and conquering and fully trusting that each area is covered, I think it’s the only way to go. You have to have that level of trust and confidence in, you know, the people around you to be able to to split it up. I I’m looking in the chat window, and I see our friend Dennis who has a question about bankers. And I think this really applies to the founders as well as Scott even though I think the question was directed to Scott. So what are some of the biggest dos and don’ts for when you’re getting inbound outreach from VCs or bankers, but maybe we’ll just focus on on bankers for now. Yeah. I mean, we obviously hear a lot from from bankers. You know, I’m I’m always appreciative when they’re, you know, pretty transparent on, you know, the company we’re talking about. I can kind of quickly assess the potential fit for Datadog. We certainly have, like, a very specific way of looking at things that and and specific priorities that we’re trying to, really zero in on at any given time. So, I I tend to appreciate when they’re, you know, transparent about, you know, which company you’re talking about so I can quickly get to, is this a fit or not, before taking much time on a on a conversation. The, so so that that tends to be, a a, you know, I guess, a do for me. I I I will you know, I don’t it’s it’s very difficult to get your head around some of these technical companies if, as a as a investment banker, especially if you don’t, you know, come from a technical background, which in most cases is is not gonna be the case. But, the extent that that you can, even work with the founders of those companies to really try to do what I said earlier, which is, like, understand, amongst the this list of potential buyers where is there, a possible fit? Because it’s it’s very easy to quickly dismiss something that on the surface doesn’t seem like, it’s well aligned. You can kinda even have an initial thought around of where that might why why, in our case, Datadog might be most interested in the company. That’s, that tends to be super helpful. I think VCs are, tend to be a little bit better at dimension this dimension. I think if you invest a lot in technical companies, you tend to develop some understanding there. A lot of those folks these days do come out of technical backgrounds to begin with. So I see that a bit more there. But, you know, that’s that’s that’s probably the the main thing. It’s just, you know, within, you know, within reason, try to be at least a little bit transparent about the situation and the the company and, you know, help us a little bit understand where there might be a a fit if it’s not super obvious. And in terms of those priorities, how transparent are core dev teams, including yours, able to be around that? Like, literally, if someone asked you on the street, hey. What are the the the top five m and a priorities? Is it is it that simple? It’s like, here they are. Yeah. We I I I talk to investors all the time about what’s interesting to us because, you know, that’s how we it’s a one very helpful way to source interesting potential companies to to acquire or at at least have a conversation with or invest in in our case because we we also invest in companies. So, you know, I do talk about areas of interest. A lot of times, those are not fully fleshed out like, hey. We’re absolutely gonna go, you know, build or buy here. But, know, there are areas that we’re spending time and trying to understand better, and the best way for us to understand them really is to talk to companies. And and, you know, these days, it’s these new companies can emerge really, really quickly, and, we wanna make sure they’re on our radar as early as possible. So we’re pretty transparent about about that with, with, you know, bankers too and and and definitely with VCs that we talk to regularly. Swat in the chat has a question, which I think, Kevin, maybe is a good one for you. So, because I think, you know, you spent I think it sounds like end to end from first contact acquisition about two years if I if I got that right with Datadog. So once that seed was sort of planted when they had reached out, How did you handle, like, sort of roadmap stuff with your team in terms of, like, hey. Here’s some features that are focused on certain customer problems. Yeah. Some of those maybe overlap with some of the interests of, say, a Datadog. Right? But at the same time, you don’t wanna build, like, for Datadog, I don’t think. Or maybe you do. You know, you tell us. But the question is really about, like, how do you manage that that you know, it could even be a conflict, I guess, within a team where maybe everyone wants to be heads down a certain direction. Be like, hey. I need to hedge a little. I need to make sure we’re building some stuff that could allow us to snap in somewhere else. At least on the product road map side, for us, we oriented entirely around what solves problems for our customers. As a result, you get more traction and better reputation in the market. And I I don’t wanna speak for Scott, but I don’t know if you’d wanna acquire a company that, you know, is oriented towards something else. But I don’t wanna dismiss Swat’s question about the potential conflicts, which I feel like maybe runs a little bit deeper than the road map question. You know? It’s like when a couple is arguing about washing the dishes, is it really about washing the dishes? Right? And we can talk about that. But, Scott, I’m curious what you’re about to say. No. No. I think I mean, you’re right that it it we want folks who are focused on the right things building for customers. And, also, we’ve definitely had situations where it felt like maybe this this particular company was doing a certain set of things just to, you know, get an acquisition specifically from Datalog in many cases done, and that that that tends to be a turnoff. Again, like, it’s great to be thoughtful about different things. And I don’t I don’t think, Jeremy, a two week sprint is what we’re talking about here. Right? Like, that that type of exercise makes sense, and plus there’s a partnership angle there as well. But, if you’re sort of, like, just trying to manufacture an outcome, you know, in a very sort of, like, short term oriented way that’s not, in furtherance of the business, that can be, you know, somewhat concerning even because, you know, at the end of day, we wanna build long term value together. So thinking about how that should come together is great. Spending, you know, three months and going down a path to satisfy an acquirer that may ultimately not be interested, priorities might change even if they were interested three months earlier, I think is, the recipe for for a lot of challenges down the road. Yeah. Well, I’d I’d love to jump in on this one as well. And just because, you know, just elements of the question, you know, getting to bigger funding rounds. And we’re looking at a series of features, and and you’re getting into disagreements. I mean, because whenever you have passionate people in a room, which you should have in, you know, a small company, how are you gonna get anywhere if you’re not passionate? There’s gonna be disagreements about priorities, about, you know, direction, those types of things. And coming back to the washing the dishes analogy, it’s like you kinda have to break down, well, what are we actually disagreeing about here, and what are the principles that we need to call out as our guiding light? Right? Like, let’s say there’s there’s two different options. Right? One set of features is really gonna drive towards your current core ICP. And maybe there’s another set of, features that are gonna drive towards maybe an upmarket play where you can start pushing your average revenue per user up, which then side effect, maybe a bigger funding round because now you’re you’re bringing in, higher value customers. Well, it comes down to, well, what’s the strategy? Right? Are we doubling down on our core? Is our core fully, you know, shored up, or are we distracting ourselves by heading in this direction purely to see if we can get an outcome that’s more of a selfish outcome? Right? The way I look at things is, like, if your principle is due for your customers and you incrementally start pushing up market, that’s great, but you can’t, you know, abandon your core. Right? And so there were a couple of disagreements we had where we just kind of okay. Let’s break it down. Like, what is our goal? Okay. Does does this feature set or this feature set align with this specified goal, and is this goal correct? Right? And so that’s really kinda what it comes down to is digging into the heart of the disagreement coming back to your customer focus. And, you know, doing right by the customer tends to do right for the company in the long run. That’s fantastic perspective. Kevin, you know, once you once you got in the door at Datadog, once the acquisition was done, is there anything you would have maybe approached differently in that previous two years beforehand? And it could be from any perspective. It could be from a product perspective. It could be from a team perspective. You know, obviously, hindsight is twenty twenty, but I’m curious, like, day one, day two, day seven, sort of in those early days, you’re like, hey. Maybe we should have done it this way or done this other thing, or I’d love to hear any thoughts you have there. Well, okay. I’ll be the first to say that, you know, we say that we have both sides of the table. I would say that it’s actually this is actually a three sided table. Right? There’s there there’s a two partners getting married, and then there’s the corp dev who’s both the matchmaker and the officiant. And so I would say that we, before the acquisition, underrated how important the the people we’re working with at Datadog would be. I think we we emphasize it a lot, and yet we’d still underrated it. I would say looking back on the past eight months that almost nothing matters compared to the fact that the people who we’re working with also have startup backgrounds, and we get along personally. That is almost all of the you know, both the day to day, like, the day to day working here and, I think, the determinants of the long term success. It’s tricky, though, because I feel like during the acquisition process, there can’t be too much contact between the two parties. Right? I would have loved to come over and hang out for weeks, but, you know, it’s a it’s a it’s a little bit difficult to make that happen. But I would have loved to go back in time and emphasize that more. In a way, we got lucky, but we’re also still a little bit in the honeymoon phase. And Jeremy, know okay. I’m not trying to make this, you know, overweight analogy, but, Jeremy, you’ve been at Bill for a couple of years. Right? Yeah. Yeah. And, honestly, it so it’s partially just the way I look at at life, but I don’t think I would have done anything differently. And, you know, at least from a, like, a pre acquisition stage because we did the best that we knew at the time. And, you know, the core values that we were focusing on was customers, employees, and the best, long term outcome for the product that we built. And, you know, from that vantage point, we absolutely did all of that. And so I’m very happy with that. Now I definitely underestimated the kinda culture shock of a very small cohesive team that talks together every single day versus, you know, an org structure with thousands of people that you now need to understand how to traverse that org and and who to go to for this and who to go to for that. But, I mean, that’s not something that you’ll get into until you’re in the company entrenched and and figuring things out anyway. So from a you know, looking back, no. I think everything went the way it needed to. Well, I think that is a perfect ending point. Benali, if you wanna just quickly pull up on the screen the final slide there. I wanted to, first of all, say thank you to Jeremy, the Bill dot com team. Scott, it was awesome to be able to do this with you. It’s been, yeah, a long time coming, so really excited about it. And, Kevin, thanks for, you know, also being a part of this. Again, really unique to have the perspective of acquired and acquirer sort of in the same room and sharing some of those experiences. So very, very excited to to be able to do that. We will be sharing recording and sort of a a wrap up post. If you’re here, you’ll be getting that shortly, and we’ll share that out. And, again, thank you so much. Really appreciate the time. We’re gonna be picking up next year with our virtual event series as well, and hope you have an awesome awesome day, awesome week, and a great holiday season. Thank you so much.
The Two-Year Relationship That Led to Acquisition
Kevin’s acquisition by Datadog didn’t happen overnight.
Datadog’s corp dev team first reached out to Metaplane, and Kevin met with their product team. A year later, when Metaplane was raising their Series A, the conversations got more serious. They didn’t close then. But Scott kept in touch—including catching up whenever Kevin visited Boston.
“We always got along really well and thought, hope that there would be an opportunity for stars to align in the future. And eventually, Kevin was ready, and so we were able to kind of re-engage at that time.”
From first contact to close: about two years; longer than Kevin has been at Datadog post-acquisition.
Jeremy’s path to Bill.com moved faster—about six months from first meeting to close—but the relationship dynamics were similar. Finmark wasn’t actively looking for an exit; they were preparing to raise a Series A when Bill.com came inbound. The initial conversations were about partnership, not acquisition. But as the fit became clear, the conversation evolved.
“There’s so much synergy in the market that we were hitting, on the problems we were solving. For the customers, this is an amazing win. For the product, we now have more eyes than we can imagine because of the scale of Bill.”
Acquirers are playing a long game. They’re tracking your progress, watching your product velocity, and building conviction over time. Having that extended lens meant Datadog could see “the delta between our first interaction, the demo we saw then, and trying the product… a year or so later.”
What Actually Gets You on the Shortlist
So how does a corp dev team build their target list? Scott broke down Datadog’s approach:
“Once you get to specific areas, like data observability… there are only so many companies there. They’re findable.”
The sourcing is multi-pronged: reading about the industry, hitting relevant conferences (Snowflake, Databricks), talking to VCs, and reaching out cold. Kevin’s strategy of positioning Metaplane as “the Datadog for data” made it easy for VCs to mention them in conversations with… Datadog.
But finding companies is the easy part. What gets corp dev excited is the interaction with the team itself.
“The most important thing is just interacting with those companies directly. What’s getting us excited is the interactions with the team… the alignment on how we feel about what we want to do together.”
And here’s a key insight for founders: don’t just show up with a generic demo.
“Have a point of view about what it is that you bring to the company, and how things might fit within the new company. It’s much easier for someone to react to what you have to say… than rely on them to come up with it on their own in the midst of their busy day.”
What Kills Deals (and What Saves Them)
Scott was direct about what makes corp dev walk away:
“Anything that feels like deception, obviously… you want to make sure you can trust the people you’re gonna be interacting with going forward.”
He praised Kevin’s transparency during the process:
“Kevin and team were great about, hey, here are the things that you should know that maybe not the best possible things, but are just things you should be aware of. It’s much better to know those things up front than sort of find them out later, because most of that stuff does end up surfacing at some point.”
The other turn-off? Building to impress an acquirer rather than building for customers.
“We’ve definitely had situations where it felt like maybe this particular company was doing a certain set of things just to get an acquisition… done. That tends to be a turn-off.”
Kevin reinforced this:
“We oriented entirely around what solves problems for our customers. As a result, you get more traction and better reputation in the market.”
Jeremy took the same approach. When Bill.com conversations shifted from partnership to potential acquisition, his evaluation stayed grounded:
“I’m really just looking at the customers, right? Like, what is this change going to mean for our customers, and what is this going to mean for our product moving forward?”
A two-week sprint to show velocity? Fine. Three months going down a path just to satisfy an acquirer? Scott called that “a recipe for a lot of challenges down the road.”
The Thing Founders Underestimate Most
When asked what he’d do differently, Kevin’s answer was striking:
“We underrated how important the people we’re working with at Datadog would be. I think we emphasize it a lot, and yet we still underrated it.”
Eight months in, his perspective is clear:
“Almost nothing matters compared to the fact that the people who we’re working with also have startup backgrounds and we get along personally. That is almost all of the day-to-day… and the determinants of the long-term success.”
Jeremy echoed this through a different lens. When considering the acquisition, his first thought wasn’t about the deal terms—it was about his team:
“We pulled in people that we had all worked with before… and the first thought was, is this a good place to land for our employees?”
The calculus included customers, product potential, and investor outcomes. But it started with people.
“Values align, customers align, the product’s gonna be beneficial, and I think my employees are gonna land in a place that fosters the same culture that I’m looking for. Everybody wins.”
Play The Game As It’s On The Board
Acquisitions that work aren’t manufactured; they’re relationships that evolve. The best founders stay focused on customers, maintain trust through transparency, and come prepared with a point of view on how the pieces fit together.
And for those navigating the process now? Kevin’s framing of fiduciary responsibility is worth remembering:
“You have to play the game as it’s on the board. If the probability of your startup going the distance is going down, and the probability of another exit is going up… you kind of owe it to yourself and your investors to have conversations with potential acquirers.”
Just make sure you’re building something worth acquiring, not building to be acquired.
Watch the full conversation above for more on internal team communication during acquisitions, how Datadog’s corp dev team is structured differently, the questions founders should be ready to answer in due diligence, and more!