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How the Best CFOs Lead Without Being the CEO | Ken Stillwell

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Jan 22, 2026

Guest

Ken Stillwell

Ken Stillwell, CFO and COO of Pegasystems, is a seasoned leader in finance and operational transformations. He discusses the nuances of supporting a CEO while providing directional clarity and trust in sales compensation changes. Ken highlights the risks of KPI obsession, advocating for a focus on meaningful metrics instead. He also compares private equity's discipline with public market challenges, reflecting on Pega's strategic shift to cloud and subscription models. His candid insights on communication and adapting goals to various teams round out this enlightening conversation.

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INSIGHT

Leverage The Second-Seat Perspective

Sitting in the second seat lets you listen, synthesize, and improve the CEO's message before it lands.
Ken Stillwell uses that vantage to close gaps in strategy communication and add contextual color.

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ADVICE

Refine Messages In Real Time

Prepare scripts but stay ready to rewrite in the moment to add useful color without being risky.
Offer contextual, low-risk statements that illuminate the quarter or strategy for investors.

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ADVICE

Read The Room Before Reacting

Read the room and surface the question behind the question by restating what you think was meant.
Use clarifying recap phrases to confirm motivations before reacting aggressively.

Get the Snipd Podcast app to discover more snips from this episode

Value of the Number-Two Perspective

02:55 • 5min

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Sharpening Investor Communication

07:29 • 5min

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Reading the Room and Managing Up

12:47 • 2min

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Mistakes from Aggression and Humility

15:02 • 5min

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When to Call Instead of Email

20:02 • 3min

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Tailoring Goals to Audiences

22:52 • 3min

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Values vs. Behaviors in Culture

25:34 • 3min

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Anchoring After Big Transformations

28:28 • 3min

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Moving Pega to Cloud: paced transition

31:12 • 1min

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Shifting Sales Compensation to ARR

32:30 • 5min

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Balancing P&L Decisions and Field Trust

37:30 • 2min

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Listening to Sales Feedback Fairly

39:17 • 16sec

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Reorganizing Sales and De-emphasizing New Logos

39:33 • 2min

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The Danger of KPI Over-obsession

41:15 • 2min

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Why Private Equity Can Drive Discipline

43:19 • 5min

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Adapting from Private to Public CFO Roles

47:57 • 2min

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Big Bet That Paid Off: Cloud Subscription Move

50:16 • 1min

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Rapid-fire Lessons: Communication & Networking

In this episode of Run the Numbers, CJ sits down with Ken Stillwell, CFO and COO of Pegasystems, to explore the realities of leading from the second seat. Ken shares hard-earned lessons from guiding Pega through the shift from term licenses to ARR and ACV, including how to rework sales compensation without losing trust or momentum. They discuss the limits of KPI obsession, the importance of directional clarity over false precision, and why private equity often drives sharper execution than public markets—and how to apply that discipline while still playing the long game.

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LINKS:

Ken on LinkedIn: https://www.linkedin.com/in/ken-stillwell-83a499a/

Pegasystems: https://www.pega.com/

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

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

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RELATED EPISODES:

How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

https://youtu.be/T2YjdoiJtFA

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:57 Sponsors — Tabs | Abacum | Brex

00:07:26 The Strategic Value of Being Number Two

00:08:46 Earnings Calls, Messaging, and Real-Time Judgment

00:10:41 Using Feedback to Sharpen Executive Communication

00:11:38 CFOs as Storytellers & Message Repetition

00:12:31 Managing Up: Reading the Room

00:13:59 Learning the Hard Way: Misreading Dynamics

00:15:18 Confidence, Aggression, and Early CFO Mistakes

00:15:58 Sponsors — Metronome | RightRev | Rillet

00:19:45 When to Email vs Pick Up the Phone

00:22:48 Tailoring Communication to Different Functions

00:23:23 Audience-Specific Messaging: “Why Me?”

00:25:24 Values vs Behaviors in Leadership

00:28:13 Why Big Changes Need Anchoring

00:31:14 Moving Pega to the Cloud

00:32:43 Rewiring Sales Comp for ARR & ACV

00:34:56 Sales Credibility Breakdowns with Customers

00:36:20 Economics vs Trust in Sales Teams

00:37:48 Balancing Field Feedback with Company Goals

00:39:17 De-Emphasizing New Logos to Fix the Sales Model

00:41:12 The Danger of Over-Obsessing on KPIs

00:42:51 Public vs Private: Incentives and Operating Discipline

00:45:57 Why Companies Go Private: Motivation Over Patience

00:47:29 The Shrinking Public Markets

00:47:57 Private vs Public CFO Mindsets

00:49:39 Meeting Investors Where They Are

00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud

00:51:29 Long-Ass Lightning Round

00:53:24 Ken’s Finance Tech Stack & Craziest Expense

00:54:39 Credits

#RunTheNumbersPodcast #CFOLeadership #ExecutiveCommunication #SalesStrategy #PublicVsPrivate

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

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