Big Bet That Paid Off: Cloud Subscription Move

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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SPONSORS:

Tabs is an AI-native revenue platform that unifies billing, collections, and revenue recognition for companies running usage-based or complex contracts. By bringing together ERP, CRM, and real product usage data into a single system of record, Tabs eliminates manual reconciliations and speeds up close and cash collection. Companies like Cortex, Statsig, and Cursor trust Tabs to scale revenue efficiently. Learn more at https://www.tabs.com/run

Abacum is a modern FP&A platform built by former CFOs to replace slow, consultant-heavy planning tools. With self-service integrations and AI-powered workflows for forecasting, variance analysis, and scenario modeling, Abacum helps finance teams scale without becoming software admins. Trusted by teams at Strava, Replit, and JG Wentworth—learn more at https://www.abacum.ai

Brex is an intelligent finance platform that combines corporate cards, built-in expense management, and AI agents to eliminate manual finance work. By automating expense reviews and reconciliations, Brex gives CFOs more time for the high-impact work that drives growth. Join 35,000+ companies like Anthropic, Coinbase, and DoorDash at https://www.brex.com/metrics

Metronome is real-time billing built for modern software companies. Metronome turns raw usage events into accurate invoices, gives customers bills they actually understand, and keeps finance, product, and engineering perfectly in sync. That’s why category-defining companies like OpenAI and Anthropic trust Metronome to power usage-based pricing and enterprise contracts at scale. Focus on your product — not your billing. Learn more and get started at https://www.metronome.com

RightRev is an automated revenue recognition platform built for modern pricing models like usage-based pricing, bundles, and mid-cycle upgrades. RightRev lets companies scale monetization without slowing down close or compliance. For RevRec that keeps growth moving, visit https://www.rightrev.com

Rillet is an AI-native ERP built for modern finance teams that want to close faster without fighting legacy systems. Designed to support complex revenue recognition, multi-entity operations, and real-time reporting, Rillet helps teams achieve a true zero-day close—with some customers closing in hours, not days. If you’re scaling on an ERP that wasn’t built in the 90s, book a demo at https://www.rillet.com/cj

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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

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