In this episode of Run the Numbers, CJ sits down with Greg Henry, CFO of 1Password and one of the most commercially minded finance leaders in tech, to break down why he left the public-company grind at Couchbase for a PLG-driven security business and what he’s relearning in the private sphere. Greg explains how forecasting changes when the product does the selling, how to think about comp and pricing in a usage-led world, and the early tells that a model is quietly over- or under-performing. He shares why CFOs should meet far more customers than they do, how finance can drive revenue without stepping on sales, and what it actually takes for a company to plan with clarity instead of reacting. Greg also recounts the near-derailing of the Couchbase IPO, reflects on the “back nine” of his career, and offers grounded advice for aspiring first-time CFOs.

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LINKS:

Greg on LinkedIn: https://www.linkedin.com/in/greghenry23/

1Password: https://1password.com/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

Behind the Earnings Calls: Couchbase CFO Greg Henry on Consumption Models & Analyst Relations

https://youtu.be/o_pDfz5a-Hw

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:57 Sponsors – RightRev | Tipalti | Aleph

00:07:03 Back in the Private Sphere: Why Greg Joined 1Password

00:07:49 Greg’s Four-Part Framework for a Great Role

00:10:12 Thinking About the “Back Nine” & Legacy

00:13:16 Transitioning to PLG & SLG at 1Password

00:15:12 Blending PLG Efficiency with Enterprise Sales

00:17:12 Sponsors – Fidelity Private Shares | Metronome | Mercury

00:20:03 B2C vs. B2B ARPU Contrast

00:22:41 Forecasting in PLG vs. Sales-Led Models

00:24:18 Building Toward Chunky Enterprise Upside

00:25:39 Comp Plans: Complexity, Pitfalls & the Alexander Group

00:27:35 Keep Comp Plans Simple & Focused on ARR

00:29:10 Why Mid-Year Comp Plan Changes Are Dangerous

00:31:04 Governance & Guardrails for SPIFFs

00:33:19 Using the CFO Network to Drive Revenue

00:34:52 Why CFOs Must Meet Customers Directly

00:36:19 Wallet Share & Being a Buyer AND a Seller

00:38:08 Why He Avoids 3-Year+ Commitments

00:40:20 How Much Discount Is a “Year” Worth?

00:42:31 Greg’s Structured Annual Planning Framework

00:43:50 3–5% Upside/Downside Menu

00:44:57 Comp Plans Must Go Out Early

00:47:23 January Compensation & System Cutover Challenges

00:48:31 Why Roadmap Alignment Must Kick Off Planning

00:50:21 Sustain / Differentiate / Durable Growth / World-Class Teams Framework

00:52:29 Couchbase IPO Almost Going Sideways

00:54:59 How to Actually Become a CFO

01:00:11 Legacy Greg Wants to Leave at 1Password

#RunTheNumbersPodcast #CFOInsights #SaaSLeadership #PLGvsSLG #FinanceStrategy

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