Run the Numbers

CJ Gustafson
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Run the Numbers is a twice-weekly podcast about financial metrics and business models, designed for ambitious people operating tech startups. It's a collection of things host CJ Gustafson (CFO at Partstech and writer of Mostly Metrics) has learned and thought about in the trenches as a tech CFO. This show is meant to serve as a playbook of sorts for the stuff CJ wishes he knew earlier in his career, both from experience and from copying people smarter than himself. Topics frequently touch upon Startup SaaS Metrics, Annual Budgeting, Financial Forecasting, Headcount, Equity, Dilution, and Fundraising – and how all of these drive business performance and growth.

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

    1D AGO

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

    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. — 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:  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 — 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

    47 min
  2. Zombie companies, ARR, and broken SaaS economics | Brett Queener

    5D AGO

    Zombie companies, ARR, and broken SaaS economics | Brett Queener

    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. — 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:  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 — 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

    1h 12m
  3. A CFO Explains the History of EBITDA

    FEB 2

    A CFO Explains the History of EBITDA

    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. — 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/ — RELATED EPISODES: How Much Revenue Do You Need to IPO in 2025? https://youtu.be/7ajWVCNVDmI — 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

    29 min
  4. “It’s Not Zero”: The CFO Rule for AI Forecasting | Dan Griggs

    JAN 29

    “It’s Not Zero”: The CFO Rule for AI Forecasting | Dan Griggs

    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. — 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:  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 — RELATED EPISODES: Inside Rocket Companies: M&A, Metrics, and Mortgage Moats | Brian Brown https://youtu.be/ttedn4AULt8 — 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

    47 min
  5. How finance shows its value beyond being the “no” department | Maria Izurieta

    JAN 26

    How finance shows its value beyond being the “no” department | Maria Izurieta

    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 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

    53 min
  6. How the Best CFOs Lead Without Being the CEO | Ken Stillwell

    JAN 22

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

    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 — 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

    55 min
  7. How Finance Becomes a GTM Partner, Not a Bottleneck | Chris Brubaker

    JAN 19

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

    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 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

    50 min
  8. The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

    JAN 15

    The CFO Case for Probabilistic Forecasting With AI | Bruno Annicq

    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

    53 min
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About

Run the Numbers is a twice-weekly podcast about financial metrics and business models, designed for ambitious people operating tech startups. It's a collection of things host CJ Gustafson (CFO at Partstech and writer of Mostly Metrics) has learned and thought about in the trenches as a tech CFO. This show is meant to serve as a playbook of sorts for the stuff CJ wishes he knew earlier in his career, both from experience and from copying people smarter than himself. Topics frequently touch upon Startup SaaS Metrics, Annual Budgeting, Financial Forecasting, Headcount, Equity, Dilution, and Fundraising – and how all of these drive business performance and growth.

Information

  • Creator
    CJ Gustafson
  • Years Active
    2024 - 2026
  • Episodes
    262
  • Rating
    Explicit
  • Copyright
    © CJ Gustafson
  • Show Website
    Run the Numbers

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