When Drew Laxton looks back on the past year at Outreach, one moment stands out—not a transaction, but a plan. The company set its annual targets, executed against them, and then exceeded expectations. “When you see green numbers at every quarterly all-hands,” Laxton tells us, “it’s amazing how that little bit of momentum just builds the company.” What surprised him most was the cultural impact: morale rose, confidence compounded, and belief followed performance.
That belief didn’t happen by accident. Laxton’s career has consistently positioned him at the intersection of numbers and narrative. He began in investment banking, where he learned early that finance only matters if people can retain the story behind it. “If you can’t tell the story, it just stays there,” he tells us. That mindset carried him from banking into operating roles, and later to Apptio, where he experienced nearly the full corporate lifecycle—from IPO preparation to public markets and eventually a private-equity take-private.
Read MoreServing as Chief of Staff during Apptio’s Vista ownership pushed him beyond traditional finance. The role, he explains, was about making sure the CEO “didn’t run into a locked door,” anticipating decisions and asking the questions leadership would need answered. That experience sharpened his instinct for alignment.
Today, as CFO of Outreach, Laxton applies those lessons through planning discipline, FP&A embedded in the business, and storytelling that connects strategy to execution. Finance, in his view, is not a back-office function—it is the force that helps people understand why the company is moving where it is going.
Made Possible By
CFOTL: Let’s ask you about Outreach…tell us about Outreach. What does this company do, and what are its offerings? Give us some detail.
Laxton: For sure. We CFOs are so trainable—I’ve heard several of your podcasts where everybody uses the party line so well—but yeah, we amplify revenue teams, is what we always say. But what does that mean? At our core, we make AEs better at their job, and what we want to do is use AI agents to improve their day to day—take away manual tasks, make them better, help them know what the next action should be. If you look at the history of the company, pretty much anybody listening to this podcast has been in an Outreach sequence. When you get that nice, smooth follow-up from a sales rep, you’re probably in one of our sequences. We built out the platform to have a conversational intelligence tool, an opportunity management tool, and a forecasting tool—so you can really run the sales process end to end, from pipeline development all the way through a closed-won deal on the Outreach platform.
About a little over a year ago, we (not really pivoted), but added AI agents on top of this, which went to GA this year. We’re taking all those manual tasks we’ve seen through years of data we’ve accumulated and automating those. It is truly agentic, and it’s absolutely amazing to watch. It’s so fun to get on a customer call and explain to them that they never interacted with an actual human to book the call—and our agents genuinely were…
CFOTL: Would you mind sharing a history of the capital structure, or an abbreviated history? Tell us the story.
Laxton: I mean, we’ve been VC-backed from the get-go, and still are to this day. We raised our Series G in 2021. We’ve raised a little shy of $500 million in the history of the company. We still have a lot of our investor board—investors on our board—that are very supportive of the company. Beyond that, no other capital raises outside of the VC rounds.
CFOTL: As a finance person—and again, you were named CFO in February 2025, but you joined back in 2020—LLMs weren’t being discussed widely. Now we’re all “AI-aware.” How has the conversation within the company evolved? Can you reflect on AI during your tenure at Outreach?
Laxton: It certainly has become a noisy market. But look, we’ve had AI in the product before. It was called AI. We were the first to understand sentiment in email responses and be able to move things around in sequences based on the responses that came back from a prospect. So AI has been there a long time. We’ve had an AI account assist basically since you saw the LLMs come out—where you could ask very general questions in natural language, like, “Is this opportunity one that I should pursue?”—and it’s going to go through all of the data and say why and what the reasons are. So AI has existed for quite a while. The big shift I’ve seen over the last year is the agentic side of it actually doing activities—not in this copilot stage, but actually augmenting the work so that people can be better at their jobs. That’s really the game changer, I think, overall.
Outreach | www.outreach.io | Seattle, WA