1154: When Finance Becomes the Company’s Storyteller | Drew Laxton, CFO, Outreach

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.

Serving 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.