Run the Numbers

In this episode of Run the Numbers, CJ sits down with PSG Managing Director Chris Nesbitt to unpack how great deals are actually found, how investment decisions are really made, and why narrative often matters more than most investors admit. They also dig into forecasting, boardroom authenticity, simple vs. complex models, and the roles of market, product, and leadership in driving outcomes.—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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cj—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/christophersnesbitt/Company: https://psgequity.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro2:44 PSG origin story4:01 Growth to 30B AUM5:07 Strategy: small software at scale5:50 Vertical SaaS treasure hunting8:10 Ministry Brands: software meets payments9:28 Sponsors — Brex | Aleph | RightRev12:46 Early M&A work and rollup strategy15:52 Sourcing is more competitive now18:28 Smoke signals and relationship sourcing21:22 Does brand get you in the room?22:15 Authenticity as a sourcing edge22:52 Sponsors — Rillet | EY | SpendHound26:09 Brand name of investor or deal partner?27:44 Investors are narrative driven animals29:18 Market, product, then execution31:26 Danger of falling in love with the narrative33:40 Operator AI pivot story: GRC company34:51 Keep it simple: one tab, five key inputs39:21 Forecasting confidence beyond 12-18 months41:51 What makes a useful board meeting45:01 Build vs. buy: the payments decision47:45 ARR vs. EBITDA multiples50:30 Lightning round50:34 Board materials: send 3 days in advance51:03 LTV to CAC and cap software debates51:32 First deal at PSG52:35 What young investors get wrong54:04 Credits

In this episode of Run the Numbers, CJ sits down with Manu Diwakar, CFO of Virta Health, to unpack why health tech breaks traditional SaaS thinking. They get into the realities of running a business where outcomes matter, half the company are medical professionals, and efficiency can’t come at the expense of care. It’s a conversation about sustainable scaling, smarter reinvestment, and building for durability over hype.—SPONSORS: SpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.com/cjBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartups—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/manu-diwakar-1aa578/Company: https://www.virtahealth.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:18 Welcome and guest intro3:02 What sector is health tech?4:34 Virta go to market explained7:01 B2B to B2C model9:00 Value based care and ROI guarantees9:18 Half the company are medical professionals10:36 Sponsors — SpendHound | Brex | Aleph14:03 Annual planning process16:42 Shape of the curve17:33 TAM: metabolic health is massive20:45 Fee for service vs. value based care24:16 Sponsors — RightRev | Rillet | EY27:24 Unique costs of health tech: billing, compliance30:54 Corporate practice of medicine31:44 North star: members under management32:43 The flywheel: $250 charge, $500 saved33:28 Early stage CFO job is easy35:28 Bad habits baked in during high growth38:02 Choosing not to profit vs. not turning a profit41:15 Running a VC-backed business for sustainability42:07 People, tech and process framework44:31 Hiring philosophy: hard work, learning, curiosity48:26 Athletes vs. experts in hiring50:03 Clock hands interview question50:49 Lightning round51:09 Screwed up: having hard conversations late51:57 Advice to younger self52:15 Finance software stack52:42 Craziest expense story53:47 Credits

In this episode of Run the Numbers, CJ sits down with Praveer Melwani, CFO of Figma, to unpack the financial model behind one of tech’s most iconic product-led companies. They cover viral growth, forecasting without a traditional sales pipeline, AI credit pricing, margin tradeoffs, and the metric Praveer believes matters most in the long run: free cash flow per share.—SPONSORS:EY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/praveer-melwani/Company: https://www.figma.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:21 Welcome and guest intro2:55 From banking to Dropbox to Figma5:04 Inflection points: building trust early8:36 TAM expansion thinking10:31 Sponsors — EY | SpendHound | Brex13:38 Two-thirds of Figma users aren't designers14:36 Forecasting product led growth16:22 Cohorts and NDR discovery17:39 LTV to CAC philosophy18:57 Product signals for account expansion20:22 How Figma achieved hypergrowth with 90%+ margins22:14 AI expands TAM: time to hit the gas23:22 AI credit pricing model24:50 Sponsors — Aleph | RightRev | Rillet28:13 Outcome based pricing consideration29:00 Where AI margins settle: gross profit dollars30:08 Free cash flow per share as north star31:04 NDR and pricing volatility32:13 Bundled vs. unbundled seats34:50 Being engaged in sales to understand admin pain35:17 IPO day experience36:27 Keeping employees focused beyond the stock price37:19 Employee stock pressure and lockup reality39:37 Kitchen cabinet of advisors41:44 How to ask better questions of advisors41:47 Lightning round41:50 Advice to younger self42:47 Finance software stack44:09 Claude WTF moment: forecasting model throughput45:13 Craziest expense story: the haircut45:59 Credits

In this episode of Run the Numbers, CJ sits down with Wealthfront CFO Alan Imberman to unpack automation as a strategy, the compounding power of retention and trust, and how to balance elite profitability with continued investment. They also discuss why Wealthfront went public earlier than many peers and what’s really happening in fintech right now.—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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/runRightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJ—LINKS: Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsNGuest: https://www.linkedin.com/in/alan-imberman-cfa-aab2371/Company: https://www.wealthfront.com/CJ: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview and intro1:37 Welcome and guest intro3:11 Wealthfront overview4:38 Automation as core philosophy6:50 55K clients per support rep example7:45 90% gross margins and $1M revenue per employee8:46 Optimization vs. exploration framework9:58 Data flywheel: the Path product10:43 Cash account insight from customer data11:26 Home lending insight from wire data13:33 Sponsors — Rillet | EY | SpendHound16:45 Product led growth and referrals18:11 Incentives vs. paid marketing20:46 Compounding philosophy and 120% NDR22:07 Long term thinking vs. public market pressure22:40 No guidance decision26:26 Sponsors — Brex | Aleph | RightRev29:44 Serving the wealth builder: 80/20 in wealth management31:45 Decision to go public at $339M revenue33:46 Does size matter for IPOs?34:46 Fintech's moment: Chime, Klarna, Circle36:49 Non-monetary benefits of going public38:30 Memos over slides40:31 Hedge fund early career: spreading 10-Ks in Excel46:45 Don't lose the forest for the trees in modeling48:31 Lightning round48:43 Screwed up: de-annualizing a fee rate49:55 Advice to younger self50:32 Finance software stack51:14 Craziest expense story: $100K coffee tab53:11 Credits#RunTheNumbersPodcast #CFO

On this week’s Run the Numbers, CJ sits down with Steve Isom of Bloomerang to break down what a “strategic CFO” really is. They cover the shift from reporting to operating, why customer orgs drive SaaS value, and how AI is reshaping the finance role. —SPONSORS:RightRev is an automated revenue recognition platform built for teams that have outgrown spreadsheets and billing tool workarounds. It handles high-volume subscriptions, usage-based contracts, and mid-cycle upgrades, so you can scale without scrambling at month-end. For RevRec that keeps your books clean, visit https://www.rightrev.com/CJRillet 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/cjEY works with high-growth tech companies to navigate the messy realities of scaling—from regulatory requirements to IPO readiness. By helping teams get it right early and often, EY lets founders stay focused on building while reducing risk as they grow. Learn more at https://www.ey.com/techstartupsSpendHound is a SaaS spend management platform built for finance and procurement teams that want visibility and leverage in every deal. By tracking all your software, benchmarking pricing across thousands of vendors, and surfacing contracts and renewals, SpendHound helps you stop overpaying and negotiate with confidence. Trusted by teams at ZoomInfo and Hootsuite. Get started at https://www.spendhound.comBrex 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/metricsAleph is a modern FP&A platform built for teams that want more than another planning tool. By connecting your ERP, CRM, and other systems into one trusted data layer with AI workflows, Aleph helps you move faster with real-time insights. Get a personalized demo at https://www.getaleph.com/run—LINKS: Steve on LinkedIn: linkedin.com/in/steveisomjrCompany: https://bloomerang.com/CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/Mostly metrics: https://www.mostlymetrics.com—TIMESTAMPS:0:00 Preview1:25 Intro2:55 Welcome Steve Isom3:13 CFO to COO promotion5:02 Having a pulse on every function6:51 Defining "strategic CFO"7:19 Tying strategy to value creation9:27 Being embedded in the rhythm of the business10:55 Finance leaders as commentators vs. team captains12:25 Sponsors — RightRev | Rillet | EY15:33 Killing projects as a core skill18:14 Activity doesn't equal impact19:16 Project Steve killed20:39 Taking over the customer org at Bloomerang22:18 Why acquisition is a cash-losing exercise23:07 LTV lives post-sale24:39 Most vulnerable area: customer success25:24 Ruthless CSM segmentation26:30 Nonprofits don't think about your software29:21 Sponsors — Spendhound | Brex | Aleph32:43 CFO running ops35:52 Metrics vs. humans37:18 Skip levels and what they reveal39:01 Incentives drive the wrong outcomes40:22 Customer-introduced delays as a key sub-metric40:27 Unit economics become tangible when you're accountable42:17 Going deep on AI45:13 Motivating your team to experiment with AI46:02 AI for personal projects47:05 Resource allocation in a vibe-coding world48:42 Does AI efficiency just mean more work?50:32 What excites Steve about the future of finance leadership52:08 Finance leaders who don't use AI won't get hired52:13 Credits#RunTheNumbersPodcast #CFO #StrategicFinance #SaaSFinance #FinanceLeadership #CFOtoCOO