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. — 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 It gives product teams the freedom to keep innovating without outdated revenue systems slowing them down.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 — 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 — 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
