When Planning Impacts Company Morale | Drew Laxton, CFO, Outreach

Описание: In this episode, Jack is joined by Drew Laxton, the CFO of Outreach. They discuss Outreach’s mission to help revenue teams execute more effectively, and how the platform has expanded from sequencing into a broader, AI-enabled workflow across pipeline, forecasting, and execution. Laxton explains why storytelling and FP&A are critical operating tools—especially when preparing board-facing asks and aligning teams around a coherent plan. The conversation also covers agentic AI, how finance teams are adopting AI for speed and insight, and the governance risks of over-trusting automated outputs. Laxton shares career lessons from banking, investor relations, and a chief-of-staff chapter, then reflects on how planning accuracy can become a surprising driver of organizational confidence.

Thanks to our sponsor Intuit QuickBooks https://quickbooks.intuit.com/money/

Video Timestamps & Titles (≤15)

0:00 — Why finance storytelling matters at the board level
0:59 — When finance shifts from tracking performance to shaping belief
1:52 — Sponsor message: Planful AI
2:53 — Meet Drew Laxton, CFO of Outreach
3:21 — Early career lessons: curiosity, business fluency, and narrative
5:19 — The “operator’s itch”: moving from banking into company-building
7:39 — Investor relations: harder questions, tighter narratives
9:18 — Chief of staff: anticipating the CEO’s needs in PE operating cadence
11:09 — The CFO “checkboxes”: IPO, capital raising, and M&A experience
13:28 — What Outreach does: revenue execution and agentic AI in action
15:07 — Capital structure overview and venture funding context
16:12 — AI’s evolution: from features to truly agentic systems
17:23 — How finance teams use AI—and why speed is the first gain
20:12 — Measuring AI ROI and managing adoption risk
27:40 — Finance Strategic Moment: when disciplined planning lifts morale
30:52 — Metrics that matter: gross retention mechanics and AI revenue alignment
32:54 — What surprised him as CFO: controllership fires and people leadership
35:05 — Returning to Outreach: leadership vision and the pull of the mission
37:02 — Book pick: The Hard Thing About Hard Things
37:43 — The next 12 months: supporting efficient growth driven by AI agents