Run the Numbers

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
—
RELATED EPISODES:
How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker
https://youtu.be/T2YjdoiJtFA
—
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

In this episode of Run the Numbers, CJ sits down with Chris Brubaker, SVP of Finance at Postscript, who’s helped build the finance function from the ground up. Chris shares how he partners with sales through deal desks, sets pricing guardrails, and makes sure finance helps close deals instead of slowing them down. They dig into his hands-on approach to automation using AI with limited engineering resources, how Postscript’s metrics evolved as the company scaled, when to trust internal data over benchmarks, and where teams get tripped up. Plus, a private jet accounting story—because of course.
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SPONSORS:
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
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
—
LINKS:
Chris on LinkedIn: https://www.linkedin.com/in/wchrisbrubaker/
Postscript: https://postscript.io/
CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
—
RELATED EPISODES:
So You’re Looking for a “Strategic” CFO? Bloomerang’s Steve Isom on What That Really Means
https://youtu.be/cgHOtvG1Ces
The IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio’s Former CFO
https://youtu.be/PTKAUD7PSWU
The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq
https://youtu.be/Dl8nDZPJMpE
—
TIMESTAMPS:
00:00:00 Preview and Intro
00:02:22 Sponsors — Rillet | Tabs | Abacum
00:06:55 Interview Begins
00:07:36 First Finance Hire and Early Scale at Postscript
00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel
00:10:31 Partnering With Sales and Building Deal Desk
00:13:16 Pricing Guardrails, Payback, and Deal Economics
00:15:35 How Deal Desk Evolves Over Time
00:16:01 Sponsors — Brex | Metronome | RightRev
00:19:44 Making Finance a Deal-Closing Partner
00:20:44 Automating Deal Desk With a Slack Bot
00:23:48 How Technical Finance Leaders Need to Be
00:25:17 Automating Without Engineering Help
00:27:12 Why Human Touch Still Matters in SaaS
00:27:53 Postscript’s Finance Tech Stack
00:28:30 ERP Migration and Month-End Efficiency
00:29:42 The Reality of Continuous Close
00:30:34 First Real AI Wins in Accounting
00:31:18 Experimenting With AI Forecasting
00:33:32 Metrics That Matter: Usage as a Leading Indicator
00:35:49 How Metrics Evolve as the Company Scales
00:37:41 Understanding the Product in a Usage-Based Model
00:39:27 Micro-Seasonality and Forecasting Volatility
00:42:21 How to Use Benchmarks Without Misusing Them
00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake
00:45:45 Advice to a Younger Finance Leader
00:47:05 The Private Jet Accounting Story
00:49:11 Credits
#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance


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

In this episode of Run the Numbers, CJ sits down with Bruno Annicq, CFO of Wellhub (formerly Gympass), to unpack a practical finance playbook built around cash discipline, sustainable growth, and simplicity. Bruno explains how he rebuilt forecasting using an AI-driven, probabilistic ensemble model, moving teams beyond single-scenario planning. They also dig into his EMPOWER planning framework, usable OKRs, and why tighter alignment between finance, HR, and wellbeing is becoming a durable lever for long-term performance.
—
SPONSORS:
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
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
—
LINKS:
Bruno on LinkedIn: https://www.linkedin.com/in/bannicq/
Wellhub: https://wellhub.com/
CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
—
RELATED EPISODES:
“Run Toward a Tough Market” — Developing the Hard and Soft Skills To Be a Great Finance Leader
https://youtu.be/iNHbkcG7YEo
—
TIMESTAMPS:
00:00:00 Preview and Intro
00:02:19 Sponsors — RightRev, Rillet, Tabs
00:06:43 Accidental CFO Origin Story
00:07:34 Consulting to Operations Pivot
00:08:12 Why Finance Clicked for Bruno
00:09:28 McKinsey Prioritization in Real World
00:10:02 Eisenhower Matrix and Prioritization
00:11:08 Investing in Non-Urgent Work
00:13:30 Lessons From AOL Reinvention
00:16:10 Sponsors — Abacum, Brex, Metronome
00:20:01 Career Growth Through Hard Problems
00:20:52 Broadening Skills Through Change
00:23:12 Five Core Finance Principles
00:24:02 Cash Is King
00:25:14 Driving Sustainable Growth
00:26:01 No Surprises and Forecasting
00:26:07 Finance as Business Enabler
00:27:22 Less Is More Philosophy
00:28:47 Hardest Principle: Less Is More
00:29:46 Deterministic vs Probabilistic Forecasting
00:31:11 Marketplace Volatility and Forecast Error
00:32:10 Ensemble Models Explained
00:33:37 Forecast Accuracy Gains
00:34:53 Building Models In-House
00:36:46 Why Explainability Matters
00:37:48 Empower Framework Introduction
00:47:47 Urgency, Compounding, Long-Term Thinking
00:48:10 Advice to Younger Self
00:50:06 Finance Stack and Expense Stories
00:52:51 Credits
#RunTheNumbersPodcast #CFO #FinanceLeadership #Forecasting #AIinFinance


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

In this episode of Run the Numbers, CJ sits down with Jason Kong, General Partner at Base10 Ventures, to unpack the firm’s focus on “automation for the real economy” — software built for industries most tech investors overlook, but the world depends on. Jason breaks down what makes Series B investing uniquely hard, how he evaluates back-office and vertical SaaS opportunities, and where markets tip from niche to overcrowded. They also discuss Base10’s decision to donate 50% of profits to fund scholarships, plus a lightning round spanning fantasy football, shorting SaaS in 2022, and a venture take that might spark debate.
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SPONSORS:
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
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
—
LINKS:
Jason on LinkedIn: https://www.linkedin.com/in/jasonykong/
Base10 Partners: https://base10.vc/
CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
—
RELATED EPISODES:
Scaling to $1B+ Revenue: From ServiceNow to Samsara | Dominic Phillips
https://youtu.be/vBY6WZBMljw
—
TIMESTAMPS:
00:00:00 Preview and Intro
00:02:20 Sponsors — Metronome, RightRev, Rillet
00:06:02 Base10 Background
00:06:41 Automation for the Real Economy
00:09:27 Vertical vs. Horizontal Software
00:10:38 Cash Flow and Durability
00:11:19 Product-Market Fit and ROI
00:12:56 Growth Limits Selling to Tech
00:13:19 The Size of the Real Economy
00:14:16 Sponsors — Tabs, Abacum, Brex
00:18:50 Base10’s Giving Model
00:20:30 Access, Education, and Tech
00:21:53 Purpose and Founder Alignment
00:22:51 Radical Transparency
00:23:56 Portfolio Focus and Strategy
00:24:05 Investing Ahead of Consensus
00:26:29 ERP Adjacency as Alpha
00:28:58 Lessons From Hedge Funds
00:32:29 Public Markets Reality
00:34:05 Public vs. Private Investing
00:34:48 The Series B Sweet Spot
00:36:49 A Bifurcated Series B Market
00:38:56 Fast Series Bs and 2021 Vibes
00:42:16 What Series B Looks Like Now
00:44:36 Back Office Automation
00:46:02 ERP-Centric Workflows
00:48:33 Long-Ass Lightning Round
00:49:36 Shorting SaaS in 2022
00:50:16 Fantasy Football and Investing
00:52:57 Career Advice That Surprises
00:55:03 A Contrarian Venture Take
00:56:22 Credits
#RunTheNumbersPodcast #SeriesB #RealEconomy #VerticalSaaS #BackOfficeAutomation


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

In this episode of Run the Numbers, CJ sits down with Dominic Phillips, CFO of Samsara, to unpack what it takes to scale a capital-intensive SaaS business from startup to public company in under a decade. Dominic reflects on his six-plus years at Samsara through hypergrowth, COVID disruption, supply chain constraints, a down-round survival raise, and an IPO at the very end of the 2021 tech window. Drawing on his earlier career at ServiceNow under Mike Scarpelli, he shares how experience across FP&A, IR, corp dev, and treasury shaped his approach to capital allocation, investor education, and analyst management. The conversation dives into asset-based pricing, selling into non-discretionary operations budgets, balancing hardware and software economics, and building credibility with a broad analyst base while scaling past $1B in ARR.
—
SPONSORS:
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
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
—
LINKS:
Dominic on LinkedIn: https://www.linkedin.com/in/dominicphillips/
Company: https://www.samsara.com/
CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
—
RELATED EPISODES:
“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth
https://youtu.be/VRpTNDIfzPY
From SMB to Enterprise: The CFO Scaling Playbook With Andrew Casey | Mostly Classics
https://youtu.be/kMuJ6gAuEpg
Driving revenue without selling | Greg Henry of 1Password
https://youtu.be/f5FsNoG8A3E
—
TIMESTAMPS:
00:00:00 Preview & Intro
00:02:40 Sponsors — Brex | Metronome | RightRev
00:06:18 Interview Begins
00:06:46 Dominic’s Early Career
00:08:47 From ServiceNow to CFO
00:09:47 Joining Samsara
00:10:54 COVID, Burn, and a Down Round
00:12:40 IPO Messaging and Investor Education
00:15:50 Sponsors — Rillet | Tabs | Abacum
00:20:27 Hardware + Software Story
00:21:29 What Samsara Does
00:22:30 Data, AI, and ROI
00:23:23 Horizontal Platform and Verticals
00:24:27 Growth Drivers at Scale
00:26:09 Selling Into Operations
00:28:19 Change Management in Legacy Orgs
00:29:46 Non-Discretionary Budgets
00:33:02 Storytelling Lessons from Scarpelli
00:36:14 Managing Analysts
00:39:23 Earnings Timing Strategy
00:41:06 Metrics and Investor Trust
00:42:38 Investor Communication Channels
00:44:22 Investor Days and Long-Term Vision
00:45:37 Annual Planning Maturity
00:48:24 Forecast Accuracy and Cadence
00:49:28 The 1000-Day Strategy
00:50:40 Top-Line and Margin Targets
00:51:59 Capital Allocation by Function
00:54:46 Becoming a CFO
00:58:21 Lightning Round and a CFO Mistake
01:02:41 End Credits
#RunTheNumbersPodcast #CFO #ScalingCompanies #B2BSaaS #PublicMarkets


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