How we took advantage of M&A
At one point in time, we completed four add-on acquisitions in eighteen months. As a CEO, doing even one acquisition while running a company is a lot of work, let alone four. M&A let us cut years off the R&D roadmap, reach new geographies in months rather than years, and bring senior people with decades of category expertise onto the team in a single move. Together those advantages let us leapfrog competitors and offer our customers a depth of capability they could not get anywhere else. Done well, each acquisition strengthened the platform without distracting the core business.
Strategy led the deals. Acquisitions had to fill gaps the company already needed to fill, and we started every potential deal by naming the specific gap, whether that was market, capability, or talent, before we evaluated any target. If a candidate did not map to a stated priority, the answer was no regardless of how attractive the asset looked on its own.
We owned the M&A function in-house because the team had the experience to do it credibly. Garrett and I, as Co-CEOs, had spent most of our careers sourcing and completing software acquisitions. Sam, our head of customer success, and Brendan, our CFO, had both executed prior transactions and run post-close integration. As we filled out the rest of the leadership team, we hired for the same kind of experience. Doing M&A poorly is worse than not doing it at all. Garrett and I split the deal cycle, covering strategy, sourcing, negotiation, and integration ownership. Brendan ran financial diligence and Sam led customer success integration. We did not outsource sourcing because the early conversations carried information we did not want filtered through a third party.
We built the market map ourselves, partnering with our company’s original founders to prioritize by strategic fit. Outreach was direct, CEO to CEO, with dozens of potential targets in conversation at any point in time. Diligence covered the standard financial and legal items, but the larger share of time was spent with our team determining fit, from a cultural, product, and sales perspective. Part of diligence was having a complete integration plan in place before we closed, with named owners on our side for product, customer success, and people. We did not announce a deal until we knew exactly how the first ninety days were going to run.
The four acquisitions pulled forward years of the product roadmap and brought senior leaders with decades of category experience under one roof. They opened markets the organic plan would have taken much longer to reach, and they gave us a permanent M&A capability inside the company that we used for years afterward.