Run the Numbers

In this episode of Run the Numbers, CJ sits down with Kunal Agarwal, CFO of Gorgias, to unpack how AI is reshaping pricing and operations. They discuss outcome-based pricing, how to forecast LLM-driven costs, and why order-to-cash isn’t just back-office plumbing—it can be a true growth lever when designed correctly.—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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/agarwalk/Company: https://www.gorgias.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and Intro2:14 PE to venture incubator4:39 Operational empathy from zero-to-one4:45 First paying user feeling5:40 Jet ski customer support story8:49 Hanging with IC sales reps12:24 Sponsors — Tabs | Abacum | Brex15:44 Finance as the decision engine17:36 Gorgias overview20:20 Pricing structure and iteration22:11 Outcome based / resolution pricing24:48 AI success rate as key metric25:33 Sponsors — Metronome | RightRev | Rillet28:57 Pricing value split — $1 per resolution31:17 Vertical specificity as AI moat33:27 Managing LLM costs35:41 Falling token costs and model mix39:28 Order to cash as growth engine43:31 Auditing order to cash at 25M ARR44:09 Manual choke points46:32 Learning density over titles48:30 SurveyMonkey as the most formative period50:07 Lightning round50:17 Listening to respond vs. listening to learn51:04 Advice to younger self52:02 Finance software stack52:45 Cortex — internal AI decision tool54:21 Craziest expense story54:52 Credits

In this episode of Run the Numbers, CJ sits down with Federico Acabbi, investment banker at RBC, to break down what’s happening across cybersecurity, infrastructure, and the broader software market. They cover why horizontal software is under pressure while security spend holds up, what it really takes to go public today, and how the IPO process actually works behind the scenes—from diligence to pricing.—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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNFederico: https://www.linkedin.com/in/federicoacabbi/rbccm.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:36 Software investability right now6:46 Cyber — CFO's #2 investment priority8:17 AI turbocharging attacks9:08 DevOps disruption10:30 Sponsors — Rillet | Tabs | Abacum13:55 IPO landscape overview14:33 Revenue and market cap benchmarks19:24 Founder share sales at IPO22:28 Secondary market vs. IPO market23:14 How many IPOs can the market digest?24:20 Investor mix for larger vs. smaller IPOs25:04 Sponsors — Brex | Metronome | RightRev28:23 Role of mutual funds in IPOs30:00 What banks actually do on an IPO31:49 Book building and allocation32:43 Research coverage35:52 NDRs and testing the waters38:59 Roadshow format — then vs. now40:41 Direct listings explained43:57 How banks make money on IPOs44:56 Fee splits between banks47:36 IPO vs. M&A — which is more attractive?51:02 Junior banking story — Nokia and the Vespa54:31 Craziest expense story56:08 Credits

In this episode of Run the Numbers, CJ sits down with financial historian and PayPal Mafia member Aman Varejee to explore the recurring patterns behind economic bubbles. Drawing on research from his upcoming book “A Brief History of Financial Bubbles”, Aman explains what defines a bubble, the psychology that fuels speculative manias, and why major technological shifts—from railways to the internet to AI—often coincide with periods of extreme market speculation.—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.comRillet 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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNAman: https://www.linkedin.com/in/aman-verjee/https://practicalvc.com/Aman’s book: https://bigbubbletrouble.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:38 Welcome and guest intro3:48 Defining a bubble6:03 Cognitive biases behind bubbles10:27 Sponsors — RightRev | Rillet | Tabs13:56 Do bubbles produce breakthroughs?14:35 Dot-com bubble — winners and losers16:00 UK railway bubble21:24 Bubble warning signs25:30 Sponsors — Abacum | Brex | Metronome28:47 Do bubbles attract grifters?31:11 Role of government in bubbles35:59 Bubble duration vs. severity37:32 2008 — roots go back to 199240:27 Are bubbles connected through time?43:38 Are we in an AI bubble?45:06 Nvidia vs. Cisco valuation comparison46:52 Circular finance in AI49:16 FP&A at PayPal under Thiel and Musk52:02 PayPal's referral campaign and LTV/CAC54:40 Book plug55:09 Credits#RunTheNumbersPodcast #Fintech #EconomicBubbles #FinanceHistory #CFO

In this episode of Run the Numbers, CJ sits down with Jason Lee, CFO of Faire, to unpack the economics of wholesale marketplaces. They break down how Faire connects independent brands with local retailers, the key metrics that matter in marketplace businesses, and ROI as a decision-making framework. Jason also shares lessons from scaling Square through its IPO and how finance leaders navigate valuation resets in private markets.—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.comRightRev 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.comRillet 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/cjTabs 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/runAbacum 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.aiBrex 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNJason: https://www.linkedin.com/in/jason-lee-11787020/Faire: https://www.faire.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro3:01 How Faire serves retailers5:49 Revenue model and retention metrics8:21 Recurring vs. reoccurring revenue11:54 Sponsors — Metronome | RightRev | Rillet15:17 Input vs. output metrics17:13 The business equation19:08 Metric ownership22:07 Killing metrics: signal to noise23:21 800 metrics at Faire24:51 Customer count as a misleading metric26:04 Sponsors — Tabs | Abacum | Brex29:25 Planning cadences at Faire32:41 When to reallocate resources36:40 ROI as a framework40:25 Portfolio view of investments43:53 Discipline is knowing where to say yes47:11 Faire's valuation reset50:49 Tender offer mechanics55:33 Screwing up IR at Square IPO56:52 Advice to younger self58:44 AI at Faire59:32 Claude connected to data warehouse1:00:16 Tariff analysis with AI1:02:38 Credits#RunTheNumbersPodcast #Marketplace #CFO #SaaS #FinanceLeadership

In this episode of Run the Numbers, CJ sits down with Mike Wilcox, CFO of Blockchain.com, to unpack the economics of crypto exchanges. They discuss how platforms serve both retail traders and institutional clients, the different ways exchanges generate revenue, and the tension between blockchain’s radical transparency and the valuable first-party data exchanges control.—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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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/runAbacum 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMike: https://www.linkedin.com/in/mike-wilcox-65078a12/https://www.blockchain.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:Here's the trimmed version:0:00 Preview and intro2:12 Tradfi to crypto transition3:49 Blockchain.com origin5:45 CFO as business partner6:01 Finance team backgrounds7:02 Banking relationships8:51 On ramps and off ramps8:51 Retail vs. institutional10:53 Sponsors — Brex | Metronome | RightRev14:09 B2C to B2B motion16:04 Shared infrastructure18:31 Go-to-market differences19:00 Brand equity and low CAC20:06 Education as top-of-funnel21:13 Institutional vs. retail volatility22:37 Exchange vs. brokerage model23:56 How brokerages make money24:06 Sponsors — Rillet | Tabs | Abacum27:31 Setting take rates29:13 Distribution flywheel30:13 Data as a moat31:13 Nigeria market playbook31:44 Crypto balance sheet33:25 Duration matching34:37 Transaction-level risk36:12 Latency arms race37:28 Stablecoins and CFOs38:13 Risk vectors40:01 Annual planning41:51 Lightning round43:00 Finance software stack43:31 Advice to younger self44:09 Credits

CJ sits down with Marshall Hawks, a 20-year veteran of venture lending and author of Venture Debt Deals. They cover the real rules of thumb behind deal sizing, why lenders underwrite likelihood of raising again (not breakout outcomes), how banks and private credit differ, the three real sources of repayment, and how to actually run a venture debt process without blowing your legal budget.---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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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/cjLINKS:Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMarshall: https://www.linkedin.com/in/marshallhawks/Marshall's website: https://www.marshallhawks.comCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comTIMESTAMPS:0:00 Preview and intro3:23 Marshall's background and the book4:47 Venture Deals as inspiration6:30 Companies Marshall has worked with6:49 The venture debt sweet spot8:01 Why venture debt follows equity raises10:55 The 25–40% rule of thumb12:08 AI companies and the limits of the rule13:58 Sponsors — Abacum | Brex | Metronome17:15 How lenders think vs. investors19:12 The three sources of repayment21:37 Venture debt and the AI boom23:52 Banks vs. private credit26:28 Sponsors — RightRev | Rillet | Tabs29:57 Private credit pricing and warrants33:04 Syndicated deals35:04 Legal timelines38:13 Who pays the legal bill?40:06 Why your GC shouldn't quarterback the deal41:30 What forecast to give your lender43:37 Reporting cadence45:57 Bad news should travel fast47:49 The Twitch case study50:19 Are we over our skis in 2026?54:50 Where to get Venture Debt Deals55:09 Credits

In this episode of Run the Numbers, CJ sits down with Superhuman’s Head of Analytics Chris Byington. They break down where analytics should sit inside a company, why dashboards often fail, and how the best teams connect metrics, OKRs, and forecasting to real decisions. Chris also explains why “ship goals” can mislead teams and what CEOs and CFOs should expect from a truly decision-driving data function.—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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNChris: https://www.linkedin.com/in/chris-byington/Superhuman: https://superhuman.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Matt Hudson Episodehttps://youtu.be/_FWGYkzhymQ—TIMESTAMPS:0:00 Preview and intro3:29 Centralized analytics team7:29 Start analytics with problems not tools9:41 Lead with the problem10:14 Align on growth model11:46 Pre-commit to decisions13:14 Sponsors — Tabs | Abacum | Brex16:35 Dashboards need growth context19:10 Where analytics should sit21:18 Pros and cons of analytics in finance23:18 Operations vs revenue org placement24:11 Hub-and-spoke analytics model25:18 What “embedded” actually means26:14 Sponsors — Metronome | RightRev | Rillet29:38 When self-service analytics works32:04 Self-serve pitfalls33:44 Buy vs build BI35:44 Analytics owns metrics38:26 Hero metric example41:41 Outcomes > shipping42:14 Set goals before build43:57 Metrics are outcome proxies46:40 Easy way to say no48:29 Start answers with yes52:17 Proving analytics impact56:19 Credits#RunTheNumbersPodcast

In this episode of Run the Numbers, CJ breaks down the 5,000-year history of marketplaces—from Mesopotamia to Amazon—and the economics behind take rates, trust layers, and vertical unbundling. We unpack Airbnb’s fee backlash, Facebook Marketplace’s hidden value, why inventory kills platforms, and how AI will reshape discovery—without eliminating the middleman.—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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNCJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.comSlacker Stuff: https://www.slackerstuff.com/Ben: https://www.linkedin.com/in/slackerstuff/—RELATED EPISODES:The Mindshare Advantage Marketplace Success With Boris Wertz of Version One Ventureshttps://youtu.be/kN61sAxw_ykThe Marketplace Plus Model Explained | Colin Gardiner of Yonder VChttps://youtu.be/VIWFVwCfyLEA CFO Explains the History of EBITDAhttps://youtu.be/JySZv_fSNqs—TIMESTAMPS:0:00 Preview1:34 Marketplace Origins2:48 The Digital Shift5:55 Unbundling of Craigslist9:56 Sponsors — Rillet | Tabs | Abacum13:21 Smart Phone Revolution17:33 Take Rate Calculations21:08 When the Marketplace Crosses the Line24:49 Sponsors — Brex | Metronome | RightRev28:09 When Fees Become Friction30:37 The Marketplace Plus Model33:26 The $100B Flea Market36:14 The Inventory Trap40:07 The Disintermediation Problem42:35 Convenience Beats Inspection45:09 AI Compresses the Marketplace47:56 You Can’t Cut Out the Middleman50:03 Credits#RunTheNumbersPodcast #Marketplaces #PlatformEconomy #Middleman #TechStrategy

CJ sits down with Mike Jung, Co-Founder and Managing Partner of Founders Circle Capital. They unpack the rise of structured liquidity, how secondaries went mainstream, and what CFOs should know before running a tender. Mike shares lessons from the dot-com era, AI’s “super cycle,” and what separates durable growth companies from hype.—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.comRillet 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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMike: https://www.linkedin.com/in/mikjunghttps://www.founderscircle.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/https://www.mostlymetrics.com—TIMESTAMPS:1:08 Founder Circle origin3:15 The founder liquidity insight5:16 Staying private longer problem6:04 Secondary market control vs chaos8:44 Secondaries over IPOs10:12 Liquidity keeps VC alive11:27 Ask Jeeves dot-com lesson12:26 $190 to $1 + AMT reality13:10 Sponsors — RightRev | Rillet | Tabs16:39 Private share opacity risk20:25 Founder + employee liquidity playbooks21:55 Early investors need liquidity too22:31 Cap table math actually matters24:17 SPV fee stacking insanity25:37 Sponsors — Abacum | Brex | Metronome28:54 Tender offer guardrails30:09 Minimum vs maximum liquidity balance33:01 Growth stage sweet spot + IPO bar rising34:17 AI Cambrian explosion34:58 Buying fear vs buying hype36:29 AI growth sustainability37:19 Founder-led advantage + product velocity38:47 TAM is created, not measured41:06 Anti-portfolio lessons43:01 What is a supercycle44:34 Do supercycles end in crashes?46:16 AI’s unprecedented adoption curve48:31 Community as a moat52:50 Earning the right to be on the cap table

In this episode of Run the Numbers, CJ sits down with Mateo Bryant, CFO of Minted. They break down Minted’s life-event flywheel and decades-long LTV, managing extreme seasonality when half the year happens in one month, and balancing long-term CAC with short-term monetization. Mateo also shares lessons from scaling Uber and Amazon globally, localization missteps, and making marketplaces work in emerging markets.—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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNMateo: https://www.linkedin.com/in/bryantmatt/Minted: https://www.minted.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Peter Oey, CFO of Grab:https://youtu.be/tdq0AZO0dLU—TIMESTAMPS:00:00 Intro03:16 Fixer to CFO05:32 Mexico City Startups09:00 Minted Flywheel10:24 LTV Expansion11:04 Entry Points12:18 CAC and Cohorts13:42 Sponsors: Metronome | RightRev | Rillet17:06 Wedding Lifecycle19:49 Holiday Forecasting22:23 Retail Calendar24:03 Cash Flow Swings25:05 Marketing Over Sales26:06 Email Limits27:41 Sponsors: Tabs | Abacum | Brex31:02 Retail Strategy35:08 Global Experience40:47 Uber Cash Economics46:04 Cost of Not Localizing50:19 Importer of Record53:17 No Google Lesson55:34 QBR Mistake56:48 High Leverage Hours59:03 Finance Stack59:50 Seven Day Cruise Expense#RunTheNumbersPodcast #MarketplaceStrategy #EcommerceFinance #GigEconomy #CFOInsights

In this episode of Run the Numbers, CJ sits down with Varsha Udayabhanu of Invisible to unpack what enterprise AI adoption actually looks like beyond the hype. They cover forward deployed engineers, eight-week solution sprints, value-based pricing when outcomes are hard to meter, ARR vs. services revenue, and why “momentum” beats traditional SaaS metrics. A tactical look at trust, expansion, and building durable AI revenue.—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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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/runAbacum 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: Varsha: https://www.linkedin.com/in/varshaudayabhanu/Company: https://invisibletech.ai/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—RELATED EPISODES:Marketing as a Form of Capital Allocation With Carta's Head of Growth Angela Winegarhttps://youtu.be/rG09ehsrWv8—TIMESTAMPS:00:00 Intro03:21 What Invisible Technologies Does05:34 Enterprise AI Adoption Gap07:38 Forward Deployed Engineers09:44 Evolving GTM in AI Services10:36 Solution Sprints12:37 Sponsor — Brex | Metronome | RightRev15:56 Upfront Investment vs. Upside18:38 Bespoke Deals20:37 Value-Based Pricing in Enterprise AI22:12 Value Sold vs. Value Delivered23:31 Enterprise Revenue as a Portfolio of Bets24:53 Time-Bound Solution Sprints27:06 Sponsor — Rillet | Tabs | Abacum30:32 Humans in the Loop & Expert Incentives33:38 Niche Human Expertise34:10 Rethinking KPIs Beyond ARR35:44 Momentum Metrics39:00 Evaluating GenAI Financial Profiles40:47 Expansion as the Atomic Unit42:19 AdTech Lessons on Distribution & Brand43:23 Why Brand Matters for Enterprise47:10 Commoditization Risk48:31 Long-Ass Lightning Round53:20 Credits

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.—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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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: 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—TIMESTAMPS:0:00 Fixing Broken Windows in Investing3:08 What an Operating Partner Actually Does5:35 Managing Nine Portfolio Companies6:07 Where PE Investors Spend Their Time9:02 Do Investors Think About You All Day?10:16 The Operator “Bermuda Triangle”12:35 Sponsors — Abacum | Brex | Metronome15:52 The CFO “Triangle of Doom”17:47 How to Become an Investor Favorite18:42 Templates Build Trust in Board Communication20:54 Using Trusted Data22:10 The Board Payback Record Scratch23:18 Building Your “Data Diet” With the Board25:19 Sponsors — RightRev | Rillet | Tabs28:47 Signs a Team Isn’t in Command31:30 Board Meetings Aren’t a Performance34:16 “20 Board Meetings—Don’t Waste Them”35:15 Ask Permission to Reallocate the Agenda37:54 When to Send Board Materials40:28 Simplifiers vs. Complicators41:58 The Simplifier Finds the One Question That Matters42:16 Three Traits of a Simplifier: Answer, Find, Do43:15 Why Complicated Operators Take You on a Ride44:26 Selling vs. Substance46:23 “Get There, Bob”47:25 Why We Hedge49:36 You Can’t Fix a Secret52:50 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.—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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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: 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—RELATED EPISODES:Why Revenue Recognition Is the Next AI Battleground | Dan Miller of RightRevhttps://youtu.be/TxhTtwmOass—TIMESTAMPS:00:00:00 Craziest Expense Story at Rivian00:01:22 Intro to Claire McDonough00:03:09 Capital Intensity and Vertical Integration at Rivian00:06:44 Raising $14B: How Rivian Planned Its IPO Capital00:10:22 Capacity Planning and Scaling R2 Production00:12:13 Sponsors — Tabs, Abacum, Brex00:15:34 Sweating Existing Capacity vs Overbuilding00:18:22 Winning EV Adoption from ICE Buyers00:22:27 How Federal EV Tax Credits Shape EV Pricing00:26:03 Sponsors — Metronome, RightRev, Rillet00:29:27 R2 as a Driver of Long-Term Profitability00:33:14 Supply Chain as the Critical Path to Launch00:36:53 Product Roadmap as the Anchor for Capital and Headcount00:39:40 Peloton and Flipkart Lessons from Banking00:43:42 Biggest Career Mistake00:44:50 Advice to Younger Self00:47:19 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.—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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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 Intro00:02:41 Why Operating Experience Matters for CFOs00:04:08 Defining Durable Growth00:06:06 Snowflake and Consumption Revenue Complexity00:10:17 Forecasting in Consumption Models00:11:29 AI’s Role in Revenue Forecasting00:12:14 Sponsors — Rillet | Tabs | Abacus AI00:15:39 Comping Sales in Usage-Based Models00:18:15 Leasing as a Software Monetization Tool00:20:47 The CFO’s Role in Sales and GTM00:22:29 How CFOs Help Close Deals00:24:14 Rev Tech vs RevOps00:26:20 Sponsors — Brex | Metronome | RightRev00:29:40 Where AI Actually Helps Rev Rec00:31:55 Deterministic vs Probabilistic AI00:33:05 Why Enterprises Hesitate on AI Agents00:34:18 Startups vs Incumbents in the AI Race00:35:13 FOMO, Overfunding, and Market Distortions00:38:13 CFO Playbooks Without Hypergrowth00:39:38 Finding PMF as a CFO00:41:15 Career Advice: Growth vs Shiny Objects00:42:00 Building the CEO–CFO Relationship00:42:49 Learning Beyond the Back Office00:43:22 Lightning Round00:44:28 Advice to My Younger Self00:45:09 Finance Tech Stack00:46:36 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.—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.comRillet 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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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.comThe Staffing Ratios Salesforce Used, with Brett Queener of Bonfire VChttps://youtu.be/lJVgstAXjJs—TIMESTAMPS:00:02:54 Welcome Brett & episode setup00:03:51 On-prem software to SaaS00:05:54 Salesforce & recurring revenue00:07:15 On-prem costs & partner bloat00:09:58 Contracts, control & comp shifts00:14:15 Lock-in, renewals & SaaS drift00:16:20 Sponsors — RightRev | Rillet | Tabs00:19:48 From buying to hiring software00:21:59 Agents change pricing & planning00:25:59 Forecasting without ARR00:28:03 Talent models break00:29:45 Sponsors — Abacum | Brex | Metronome00:33:01 Rethinking sales & comp00:36:47 Selling by doing the job00:40:50 The future role of sales00:46:10 Zombie SaaS & category collapse00:51:07 Context as the moat00:56:07 Where AI hits next00:58:44 Vertical AI & hidden TAMs01:02:12 $1B startups vs mega rounds01:05:48 Dilution, fund math & pressure01:08:03 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.—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.comRightRev 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.comRillet 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/cjTabs 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/runAbacum 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.aiBrex 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.comSlacker 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 Intro00:01:17 The Origins of EBITDA00:06:48 Sponsors — Metronome | RightRev | Rillet00:10:12 The Mechanics of EBITDA00:13:46 Impact on Other Industries00:15:38 The Many Faces of EBITDA00:19:09 Sponsors  — Tabs | Abacum | Brex00:22:30 EBITDA’s AI Encore00:24:56 Wrap Up00:28:19 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.—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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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/runAbacum 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 Brownhttps://youtu.be/ttedn4AULt8—TIMESTAMPS:00:00:00 Cold Open00:01:03 Dan Griggs and Intercom’s AI Pivot00:02:45 Ice Cream to SaaS00:04:19 Learning the Business00:06:26 Operational Reality and Forecasts00:08:00 “It’s Not Zero” Forecasting00:10:09 Scenario Planning and Ambiguity00:11:23 Sponsors — Brex | Metronome | RightRev00:14:43 Mental Models for Metrics00:16:15 Mental Math for Forecasts00:17:28 Core CFO Ratios00:19:13 Intercom’s Burn-the-Boats Moment00:20:53 AI as an Existential Bet00:22:21 SaaS Categories AI Can Replace00:23:04 Why Finance Lags on AI00:23:39 Sponsors — Rillet | Tabs | Abacum00:27:05 Why Fin Uses Outcome Pricing00:28:59 The $0.99 Resolution Tradeoff00:30:46 Why Support Work Varies00:32:01 AI Resolution Unit Economics00:33:08 Model Choice as Costs Fall00:35:19 Domain-Specific vs Generic LLMs00:36:08 Selling Against the Core00:38:50 Founder vs Professional CEOs00:41:47 Hiring Mistakes and Instincts00:44:28 Intercom’s Finance Stack00:45:49 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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/cjTabs 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 Stillwellhttps://youtu.be/O4cx9NBqQso—TIMESTAMPS:00:00:00 Preview and Intro00:01:01 Maria’s Background00:03:09 People-First Team Building00:05:16 People, Process, Systems at Scale00:07:13 Removing Friction Outside Finance00:09:15 Data Transparency & Decision-Making00:11:06 Sponsors — Abacum | Brex | Metronome00:14:22 Forward-Deployed Data00:16:21 Centralized Data vs. Silos00:19:23 Finance as Data Steward00:21:08 Cost-to-Price Feedback Loop00:22:35 Curiosity Builds Credibility00:23:43 Sponsors — RightRev | Rillet | Tabs00:27:12 Trust First, Then Impact00:30:27 Celebrating Small Wins00:31:21 From Transactions to Insights00:33:00 CFO at the Revenue Table00:34:32 Educating the Org on Metrics00:36:21 Customer-Level Margin Reality00:37:13 Using Facts to Change Decisions00:38:27 Ownership Mindset in Growth Companies00:39:10 VC vs. PE vs. Public CFO Tradeoffs00:41:02 Operating Inside Constraints00:42:18 Finding Your Stage Fit00:44:17 Building a Personal Advisor Network00:46:43 Visibility and Women in Leadership00:47:44 Work–Life Integration, Not Balance00:48:45 Lightning Round: Biggest Mistake00:50:10 Advice to Younger Self00:51:36 Finance Tech Stack00:52:01 Craziest Expense Story00:52:44 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

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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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.comRillet 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 Brubakerhttps://youtu.be/T2YjdoiJtFA—TIMESTAMPS:00:00:00 Preview and Intro00:02:57 Sponsors — Tabs | Abacum | Brex00:07:26 The Strategic Value of Being Number Two00:08:46 Earnings Calls, Messaging, and Real-Time Judgment00:10:41 Using Feedback to Sharpen Executive Communication00:11:38 CFOs as Storytellers & Message Repetition00:12:31 Managing Up: Reading the Room00:13:59 Learning the Hard Way: Misreading Dynamics00:15:18 Confidence, Aggression, and Early CFO Mistakes00:15:58 Sponsors — Metronome | RightRev | Rillet00:19:45 When to Email vs Pick Up the Phone00:22:48 Tailoring Communication to Different Functions00:23:23 Audience-Specific Messaging: “Why Me?”00:25:24 Values vs Behaviors in Leadership00:28:13 Why Big Changes Need Anchoring00:31:14 Moving Pega to the Cloud00:32:43 Rewiring Sales Comp for ARR & ACV00:34:56 Sales Credibility Breakdowns with Customers00:36:20 Economics vs Trust in Sales Teams00:37:48 Balancing Field Feedback with Company Goals00:39:17 De-Emphasizing New Logos to Fix the Sales Model00:41:12 The Danger of Over-Obsessing on KPIs00:42:51 Public vs Private: Incentives and Operating Discipline00:45:57 Why Companies Go Private: Motivation Over Patience00:47:29 The Shrinking Public Markets00:47:57 Private vs Public CFO Mindsets00:49:39 Meeting Investors Where They Are00:50:16 A Risky Decision That Paid Off: Going All-In on the Cloud00:51:29 Long-Ass Lightning Round00:53:24 Ken’s Finance Tech Stack & Craziest Expense00:54:39 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.—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/cjTabs 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/runAbacum 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.aiBrex 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/metricsMetronome 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.comRightRev 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 Meanshttps://youtu.be/cgHOtvG1CesThe IPO Playbook: Expert Advice from Lee Kirkpatrick, Twilio’s Former CFOhttps://youtu.be/PTKAUD7PSWUThe CFO Case for Probabilistic Forecasting With AI | Bruno Annicqhttps://youtu.be/Dl8nDZPJMpE—TIMESTAMPS:00:00:00 Preview and Intro00:02:22 Sponsors — Rillet | Tabs | Abacum00:06:55 Interview Begins00:07:36 First Finance Hire and Early Scale at Postscript00:09:02 Usage-Based Margins, COGS, and the Twilio Parallel00:10:31 Partnering With Sales and Building Deal Desk00:13:16 Pricing Guardrails, Payback, and Deal Economics00:15:35 How Deal Desk Evolves Over Time00:16:01 Sponsors — Brex | Metronome | RightRev00:19:44 Making Finance a Deal-Closing Partner00:20:44 Automating Deal Desk With a Slack Bot00:23:48 How Technical Finance Leaders Need to Be00:25:17 Automating Without Engineering Help00:27:12 Why Human Touch Still Matters in SaaS00:27:53 Postscript’s Finance Tech Stack00:28:30 ERP Migration and Month-End Efficiency00:29:42 The Reality of Continuous Close00:30:34 First Real AI Wins in Accounting00:31:18 Experimenting With AI Forecasting00:33:32 Metrics That Matter: Usage as a Leading Indicator00:35:49 How Metrics Evolve as the Company Scales00:37:41 Understanding the Product in a Usage-Based Model00:39:27 Micro-Seasonality and Forecasting Volatility00:42:21 How to Use Benchmarks Without Misusing Them00:43:50 Long-Ass Lightning Round: A Costly Modeling Mistake00:45:45 Advice to a Younger Finance Leader00:47:05 The Private Jet Accounting Story00:49:11 Credits#RunTheNumbersPodcast #FinanceLeadership #DealDesk #UsageBasedSaaS #AIinFinance This is a public episode. 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