Run the Numbers

In this episode, CJ talks with Paul Stansik of ParkerGale Capital about what separates Simplifiers from Complicators. They unpack why most board meetings miss the point, how to answer the actual question, and why naming the real problem builds trust.

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SPONSORS:

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

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

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LINKS: 

Paul on LinkedIn: https://www.linkedin.com/in/paulstansik/

ParkerGale Capital: https://www.parkergale.com/

https://hellooperator.substack.com/

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

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

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TIMESTAMPS:

0:00 Fixing Broken Windows in Investing

3:08 What an Operating Partner Actually Does

5:35 Managing Nine Portfolio Companies

6:07 Where PE Investors Spend Their Time

9:02 Do Investors Think About You All Day?

10:16 The Operator “Bermuda Triangle”

12:35 Sponsors — Abacum | Brex | Metronome

15:52 The CFO “Triangle of Doom”

17:47 How to Become an Investor Favorite

18:42 Templates Build Trust in Board Communication

20:54 Using Trusted Data

22:10 The Board Payback Record Scratch

23:18 Building Your “Data Diet” With the Board

25:19 Sponsors — RightRev | Rillet | Tabs

28:47 Signs a Team Isn’t in Command

31:30 Board Meetings Aren’t a Performance

34:16 “20 Board Meetings—Don’t Waste Them”

35:15 Ask Permission to Reallocate the Agenda

37:54 When to Send Board Materials

40:28 Simplifiers vs. Complicators

41:58 The Simplifier Finds the One Question That Matters

42:16 Three Traits of a Simplifier: Answer, Find, Do

43:15 Why Complicated Operators Take You on a Ride

44:26 Selling vs. Substance

46:23 “Get There, Bob”

47:25 Why We Hedge

49:36 You Can’t Fix a Secret

52:50 Credits

In this episode of Run the Numbers, CJ Gustafson talks with Rivian CFO Claire McDonough about financing one of the most capital-intensive businesses in the world. They cover long-term investment decisions, capacity planning, cash management as production scales, lessons from Rivian’s nearly $14B IPO, the risks of over- and under-building, and why federal EV tax credits matter more than most people think.

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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: 

Claire on LinkedIn: https://www.linkedin.com/in/claire-rauh-mcdonough-5291b946/

Rivian: https://rivian.com/

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

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

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RELATED EPISODES:

Why Revenue Recognition Is the Next AI Battleground | Dan Miller of RightRev

https://youtu.be/TxhTtwmOass

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TIMESTAMPS:

00:00:00 Craziest Expense Story at Rivian

00:01:22 Intro to Claire McDonough

00:03:09 Capital Intensity and Vertical Integration at Rivian

00:06:44 Raising $14B: How Rivian Planned Its IPO Capital

00:10:22 Capacity Planning and Scaling R2 Production

00:12:13 Sponsors — Tabs, Abacum, Brex

00:15:34 Sweating Existing Capacity vs Overbuilding

00:18:22 Winning EV Adoption from ICE Buyers

00:22:27 How Federal EV Tax Credits Shape EV Pricing

00:26:03 Sponsors — Metronome, RightRev, Rillet

00:29:27 R2 as a Driver of Long-Term Profitability

00:33:14 Supply Chain as the Critical Path to Launch

00:36:53 Product Roadmap as the Anchor for Capital and Headcount

00:39:40 Peloton and Flipkart Lessons from Banking

00:43:42 Biggest Career Mistake

00:44:50 Advice to Younger Self

00:47:19 Rivian’s Finance Software Stack

In this episode of Run the Numbers, CJ Gustafson sits down with Dan Miller, CFO at RightRev. They unpack why leasing is underused in software, how RevTech emerged, and why revenue recognition may be the next AI battleground. Dan also shares how he evaluates durable growth vs. hypergrowth.

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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

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LINKS: 

Dan on LinkedIn: https://www.linkedin.com/in/danmillercpa/

RightRev: https://www.rightrev.com/

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

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

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:41 Why Operating Experience Matters for CFOs

00:04:08 Defining Durable Growth

00:06:06 Snowflake and Consumption Revenue Complexity

00:10:17 Forecasting in Consumption Models

00:11:29 AI’s Role in Revenue Forecasting

00:12:14 Sponsors — Rillet | Tabs | Abacus AI

00:15:39 Comping Sales in Usage-Based Models

00:18:15 Leasing as a Software Monetization Tool

00:20:47 The CFO’s Role in Sales and GTM

00:22:29 How CFOs Help Close Deals

00:24:14 Rev Tech vs RevOps

00:26:20 Sponsors — Brex | Metronome | RightRev

00:29:40 Where AI Actually Helps Rev Rec

00:31:55 Deterministic vs Probabilistic AI

00:33:05 Why Enterprises Hesitate on AI Agents

00:34:18 Startups vs Incumbents in the AI Race

00:35:13 FOMO, Overfunding, and Market Distortions

00:38:13 CFO Playbooks Without Hypergrowth

00:39:38 Finding PMF as a CFO

00:41:15 Career Advice: Growth vs Shiny Objects

00:42:00 Building the CEO–CFO Relationship

00:42:49 Learning Beyond the Back Office

00:43:22 Lightning Round

00:44:28 Advice to My Younger Self

00:45:09 Finance Tech Stack

00:46:36 Credits

In this episode of Run the Numbers, CJ sits down with Brett Queener, Managing Director at Bonfire Ventures, to trace the origins of ARR and examine how new revenue models are reshaping B2B software. Drawing on Brett’s time at Salesforce and SmartRecruiters, they explore the shift from annual contracts to outcome-based pricing, what it means for forecasting and gtm strategy, and where the next major inflection points in SaaS are likely to emerge.

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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

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LINKS: 

Brett on LinkedIn: https://www.linkedin.com/in/brettqueener/

Brett’s Substack: https://queener.substack.com/

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

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

The Staffing Ratios Salesforce Used, with Brett Queener of Bonfire VC

https://youtu.be/lJVgstAXjJs

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TIMESTAMPS:

00:02:54 Welcome Brett & episode setup

00:03:51 On-prem software to SaaS

00:05:54 Salesforce & recurring revenue

00:07:15 On-prem costs & partner bloat

00:09:58 Contracts, control & comp shifts

00:14:15 Lock-in, renewals & SaaS drift

00:16:20 Sponsors — RightRev | Rillet | Tabs

00:19:48 From buying to hiring software

00:21:59 Agents change pricing & planning

00:25:59 Forecasting without ARR

00:28:03 Talent models break

00:29:45 Sponsors — Abacum | Brex | Metronome

00:33:01 Rethinking sales & comp

00:36:47 Selling by doing the job

00:40:50 The future role of sales

00:46:10 Zombie SaaS & category collapse

00:51:07 Context as the moat

00:56:07 Where AI hits next

00:58:44 Vertical AI & hidden TAMs

01:02:12 $1B startups vs mega rounds

01:05:48 Dilution, fund math & pressure

01:08:03 Choosing your founder path

In this special CFO Explains episode of Run the Numbers, CJ Gustafson sits down with executive producer Ben Hillman to unpack the real history of EBITDA. From John Malone and cable TV to private equity, SaaS, and today’s AI boom, CJ explains how a metric invented out of desperation became the default language of valuation—and how adjusted EBITDA can both clarify and distort the truth about a business.

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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: 

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

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

Slacker Stuff: https://www.slackerstuff.com/

Ben on LinkedIn: https://www.linkedin.com/in/slackerstuff/

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RELATED EPISODES:

How Much Revenue Do You Need to IPO in 2025?

https://youtu.be/7ajWVCNVDmI

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TIMESTAMPS:

00:00:00 Intro

00:01:17 The Origins of EBITDA

00:06:48 Sponsors — Metronome | RightRev | Rillet

00:10:12 The Mechanics of EBITDA

00:13:46 Impact on Other Industries

00:15:38 The Many Faces of EBITDA

00:19:09 Sponsors  — Tabs | Abacum | Brex00:22:30 EBITDA’s AI Encore

00:24:56 Wrap Up

00:28:19 Credits

#RunTheNumbersPodcast #CFOExplains #EBITDA #FinancePodcast #BusinessMetrics

In this episode of Run the Numbers, CJ sits down with Intercom CFO Dan Griggs to discuss pricing and forecasting in the AI era. Dan shares the “it’s not zero” rule, the logic behind Fin’s $0.99 pricing, and how to bet on AI without blowing up the core business.

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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

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LINKS: 

Dan on LinkedIn: https://www.linkedin.com/in/dan-griggs-0970181/

Intercom: https://www.intercom.com/

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

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

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RELATED EPISODES:

Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown

https://youtu.be/ttedn4AULt8

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TIMESTAMPS:

00:00:00 Cold Open

00:01:03 Dan Griggs and Intercom’s AI Pivot

00:02:45 Ice Cream to SaaS

00:04:19 Learning the Business

00:06:26 Operational Reality and Forecasts

00:08:00 “It’s Not Zero” Forecasting

00:10:09 Scenario Planning and Ambiguity

00:11:23 Sponsors — Brex | Metronome | RightRev

00:14:43 Mental Models for Metrics

00:16:15 Mental Math for Forecasts

00:17:28 Core CFO Ratios

00:19:13 Intercom’s Burn-the-Boats Moment

00:20:53 AI as an Existential Bet

00:22:21 SaaS Categories AI Can Replace

00:23:04 Why Finance Lags on AI

00:23:39 Sponsors — Rillet | Tabs | Abacum

00:27:05 Why Fin Uses Outcome Pricing

00:28:59 The $0.99 Resolution Tradeoff

00:30:46 Why Support Work Varies

00:32:01 AI Resolution Unit Economics

00:33:08 Model Choice as Costs Fall

00:35:19 Domain-Specific vs Generic LLMs

00:36:08 Selling Against the Core

00:38:50 Founder vs Professional CEOs

00:41:47 Hiring Mistakes and Instincts

00:44:28 Intercom’s Finance Stack

00:45:49 Craziest Expense Request

In this episode of Run the Numbers, CJ sits down with Maria Izurieta, CFO of Huntress, to unpack what it really means to lead finance as a connective tissue across the organization. Drawing on experience across VC-backed, PE-owned, and public companies, Maria shares how she balances impact versus perfection, builds trust through small wins, and helps teams move from transactional finance to insight-driven decision making. They dig into data transparency, centralized BI, partnering with sales and marketing on revenue, and why the best CFOs unblock friction instead of becoming the “no” department — all while bringing a deeply people-first lens to scale.

—

SPONSORS:

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

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

—

LINKS:

Maria on LinkedIn: https://www.linkedin.com/in/maria-izurieta-909a3b/

Company: https://www.huntress.com/

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

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

—

RELATED EPISODES:

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

https://youtu.be/O4cx9NBqQso

—

TIMESTAMPS:

00:00:00 Preview and Intro

00:01:01 Maria’s Background

00:03:09 People-First Team Building

00:05:16 People, Process, Systems at Scale

00:07:13 Removing Friction Outside Finance

00:09:15 Data Transparency & Decision-Making

00:11:06 Sponsors — Abacum | Brex | Metronome

00:14:22 Forward-Deployed Data

00:16:21 Centralized Data vs. Silos

00:19:23 Finance as Data Steward

00:21:08 Cost-to-Price Feedback Loop

00:22:35 Curiosity Builds Credibility

00:23:43 Sponsors — RightRev | Rillet | Tabs

00:27:12 Trust First, Then Impact

00:30:27 Celebrating Small Wins

00:31:21 From Transactions to Insights

00:33:00 CFO at the Revenue Table

00:34:32 Educating the Org on Metrics

00:36:21 Customer-Level Margin Reality

00:37:13 Using Facts to Change Decisions

00:38:27 Ownership Mindset in Growth Companies

00:39:10 VC vs. PE vs. Public CFO Tradeoffs

00:41:02 Operating Inside Constraints

00:42:18 Finding Your Stage Fit

00:44:17 Building a Personal Advisor Network

00:46:43 Visibility and Women in Leadership

00:47:44 Work–Life Integration, Not Balance

00:48:45 Lightning Round: Biggest Mistake

00:50:10 Advice to Younger Self

00:51:36 Finance Tech Stack

00:52:01 Craziest Expense Story

00:52:44 Credits

#RunTheNumbersPodcast #CFOLeadership #ScalingCompanies #DataDrivenDecisions #ExecutiveLeadership

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.

—

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

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.

—

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

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