Run the Numbers

In this episode of Run the Numbers, CJ sits down with Wisam Hirzalla, Head of Product at Stripe Billing, to trace the full journey of a dollar—from product packaging and pricing through quoting, contracts, billing, tax, collections, and revenue recognition.
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SPONSORS:
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
EY has been part of Silicon Valley since it was just a valley, helping the most successful names in tech go from startup to exit to megacap. With teams across strategy, tax, audit, and transactions, EY helps you get your financials right early, long before your investors start asking for it. You build the next big thing, and EY will help you build it right. Learn more at https://www.ey.com/techstartups
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/wisam-hirzalla-9b20a91/
Company: https://stripe.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 What Drives Billing Downstream
1:41 Welcome to Run the Numbers
2:37 Wisam's Path to "Queen of Billing"
4:55 What Head of Billing at Stripe Entails
5:45 Defining Quote-to-Cash
7:50 Layer 1: Pricing and Packaging Mistakes
14:46 Pricing Models Rising Because of AI
18:11 Layer 2: Inside a Quote
19:27 Why Enterprise Deals Get So Messy
24:38 Layer 3: Contracting
27:21 Layer 4: Billing
30:15 Why Usage-Based Billing Is So Complex
34:51 Tokens as a Pricing Unit
36:57 Billing's Move Out of the ERP
39:53 Layer 5: Provisioning and Entitlements
43:36 Layer 6: Tax
44:27 Layer 7: Getting Paid
48:18 Layer 8: RevRec
50:52 When Billing Stopped Being Back Office
51:47 Asking Better Questions Segment
52:28 Will AI Replace Finance Jobs

Front CFO & COO Meredith Finn joins CJ to explain why finance leaders are taking on more of the operator’s job. They break down the CFO-COO dual mandate, how Front funds new bets inside a mature SaaS business, why AI requires more coordination than simply handing everyone new tools, and how finance teams should think about the growing cost of AI.
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SPONSORS:
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/meredithfinn1/
Company: https://front.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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RELATED EPISODES:
Adam Swiecicki - CFO of Rippling
https://youtu.be/JyGJVpmZNac
Aurélien Nolf - CFO of Navan
https://youtu.be/siwzJSRXAvY
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TIMESTAMPS:
0:00 The CFO/COO Dual Mandate
1:45 Welcome to Run the Numbers
2:52 Front's In-House Podcast Studio
3:41 Meredith's Investment Thesis on Front
7:21 The "Portfolio Career" Analogy
8:35 What She Had to Unlearn as an Operator
13:13 Books on Strategy vs. Execution
16:17 When a CFO Should Also Be COO
18:27 What the COO Hat Actually Covers
20:20 Where the Two Roles Conflict
25:42 Budgeting for AI Token Costs
29:16 Using Internal Usage as a Benchmark
35:40 Funding a Series A Bet Inside a Series D Company
38:04 Sizing Bets: Core, Adjacent, Moonshot
40:04 The Secret to Re-Accelerating Growth
41:46 Going Deeper, Not Wider
43:18 What the Pricing Overhaul Taught Her
47:30 Why Customer P&L Matters
50:11 Lightning Round Begins
51:32 Advice to Her Younger Self
52:33 Front's Finance Tool Stack
53:21 Craziest Expense Ever
#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #SaaSGrowth

In this episode of Run the Numbers, CJ Gustafson sits down with Xero CFO Claire Bramley to discuss how the CFO role is expanding beyond finance into strategy, operations, transformation, and technology. Claire also shares how she builds teams around her weaknesses, what small businesses actually want from AI, and why she views diversity as a business performance decision.
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SPONSORS:
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/claire-bramley-133b7174/
Company: https://www.xero.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:00 Xero and CJ's History With It
4:12 Xero's Size and Scale Today
5:10 The Expanding CFO Role
7:06 Hiring Experts You're Not
8:47 Imposter Syndrome
11:00 Getting Better at Asking Questions
15:04 Asking the "Stupid Question"
16:21 Finance as the Corporate Junk Drawer
17:48 The Trial Period Idea
18:24 Tripwires: Leading Indicators for CFOs
25:35 AI Hype vs. Main Street Reality
26:44 What Small Business Owners Actually Want
28:45 What Big Corps Underestimate
31:10 Trust as a Competitive Moat
33:45 Why the Line Is Thinner for Small Biz
35:12 AI Inside Claire's Finance Team
37:23 AI for Investor Relations
39:28 Diversity as Capital Allocation
42:07 A Decision Diversity Changed
44:45 Lightning Round Begins
46:06 Advice to Her Younger Self
48:49 Craziest Expense Ever
#RunTheNumbersPodcast #CFOLife #FinanceLeadership #AIinFinance #WomenInFinance

On this episode of Run the Numbers, CJ and Ben trace corporate private jets from Sam Walton’s scrappy two-seater to Alex Karp’s $17 million jet bill. They break down when flying private actually makes business sense, how jets hit the balance sheet, the tax and accounting implications, what companies disclose to investors, and when executive travel crosses the line from productivity tool to corporate excess.
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SPONSORS:
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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RELATED EPISODES:
Jersey Mike’s IPO: The $4.2B Sandwich Machine
https://youtu.be/ZL6AbqHI-0g
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TIMESTAMPS:
0:00 Fly Like a G6
0:29 $17M on jets: Alex Karp guess
1:16 Sam Walton starts it all
2:49 The yellow legal pads
4:37 Walmart Aviation founded (1968)
5:14 Piston to Bombardier jets
6:51 Walmart's modern jet fleet
8:13 Where it hides in SEC filings
9:25 SEC Reg S-K Item 402
13:37 Gulfport Energy scandal
14:42 Tyco: Kozlowski & Schwartz
16:57 When jets are actually useful
17:55 P&L vs. balance sheet treatment
18:40 PP&E and depreciation basics
19:04 Off-balance-sheet leases
19:28 The chartering loophole
19:54 "Uber Jet" fractional ownership
23:14 How activists hunt jet spend
23:36 Flight registries & tail numbers
24:13 Jack Sweeney vs. Elon Musk
25:00 What top companies spend
25:18 Walmart's fleet is #1
26:17 Charter vs. lease vs. own
29:02 Should we care? 3 angles
30:06 Angle 2: opportunity cost
30:59 Angle 3: company size
31:42 General Electric's shadow jet
32:50 Back to Alex Karp
34:02 Credits
#RunTheNumbersPodcast #PrivateJets #CorporateFinance #ExecutivePerks #CFOLife

On this episode of Run the Numbers, CJ Gustafson sits down with Richard Haram, VP of Finance at RapidSOS, to unpack how finance supports a public safety AI platform that helps 911 operators and first responders act faster. They cover building AI fluency, combining FP&A with BI, monetizing vertical software, integrating acquisitions, and the leadership lessons Richard carried from entrepreneurship.
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SPONSORS:
Pulley is an equity management platform that lets you issue options, model dilution, and complete 409As without your cap table turning into a spreadsheet disaster. Founders raising, hiring, and scaling use Pulley to keep equity clean and stay focused on building. Learn more or request a demo at https://pulley.com/mostlymetrics
Rillet is an AI-native ERP built for modern finance teams that want to replace NetSuite and close faster. With revenue recognition, close management, multi-entity support, and native Stripe and Salesforce integrations, Rillet helps scaling companies run their finance stack in one place. Hundreds of teams, including Windsurf and Mercor, use Rillet to make the zero-day close real. Book a demo at https://www.rillet.com/cj
Maximor is an autonomous finance platform that runs order-to-cash, procure-to-pay, the close, cash management, and reporting on self-learning agents instead of a dozen disconnected tools. One PE-backed customer posts 98% of transactions directly to its ERP, with the remaining 2% routed to a human for review. You pay for outcomes, not seats. See it at https://www.maximor.ai/
Brex is an intelligent finance platform with AI-powered workflows that enforce expense policies at the point of sale, match receipts automatically, and reduce month-end close from weeks to hours. Thousands of companies, including Anthropic, Coinbase, and DoorDash, already run on Brex. Stop asking A-level finance talent to do B-level admin work. Learn more at https://www.brex.com/metrics
Anrok is the sales tax platform that watches your exposure everywhere, automates compliance, and flags risk before it turns into a surprise back-tax letter from a state you've never set foot in. Companies like Anthropic, Notion, and Vanta already trust Anrok to stay ahead of rules that move faster than any spreadsheet can. Talk to a sales tax expert for a personalized exposure estimate at https://www.anrok.com/rtn
RightRev is a revenue recognition platform built for the AI economy, helping finance support usage-based pricing, credits, hybrid contracts, seats plus consumption, and whatever commercial model comes next. It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down. Learn how RightRev can help at https://rightrev.com/cj
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LINKS: 
Mostly Talent: https://mostlymetrics.typeform.com/to/cLTxtAsN
Guest: https://www.linkedin.com/in/richardharem/
Company: https://rapidsos.com/
CJ: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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TIMESTAMPS:
0:00 Preview and Intro
3:10 What RapidSOS does
4:59 CJ’s own car accident
5:33 What's broken about 911
6:50 Who's the actual customer
7:46 How RapidSOS monetizes
10:13 Sponsors — Pulley | Rillet | Maximor
13:27 Too much data, too much noise
16:35 Data pollution and trust
18:24 The data stack early on
19:25 Should BI have come sooner?
20:45 The framework: questions to decisions
22:43 Building a data culture
23:58 Sponsors — Brex | Anrok | RightRev
26:51 Bottoms-up vs. top-down AI
28:42 Inspiration, not training
32:24 The three-phase AI progression
33:31 Founding an AV company at 8
35:37 Giving people room to grow
38:12 Depending on heroes
39:55 Working under founder personalities
41:23 Do startups undervalue what they sell
42:48 A price hike, zero churn
43:24 Signs you're underpricing
44:57 Lightning round
45:03 Screwed up: refreshed data before a demo
47:15 Advice to younger self
47:41 Finance software stack
48:37 Craziest expense: personal gas
49:29 Credits