Virtual Event: What Really Happens Inside an Acquisition (From Both Sides of the Table)

“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.

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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!

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