Blake Grayson, CFO of Docusign, joins CJ Gustafson to discuss how a company that redefined e-signature and became a verb is now navigating its next chapter in intelligent agreement management. Drawing on more than a decade at Amazon—where he helped forecast AWS and worked inside some of the company’s most operationally demanding businesses—Blake explains how financial discipline, operational depth, and clear narrative-building shape his approach as CFO. The conversation explores how to evolve a beloved product without diluting the brand, why pricing is as much about positioning as revenue, how to communicate go-to-market mechanics without losing the room, and why effective capital allocation accepts that not every big bet needs to land to shape the leader you become. — SPONSORS: Fidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at and mention Mostly Metrics to get 20% off. Sage Intacct is a cloud financial management platform that replaces spreadsheets, automates workflows, and keeps your books audit-ready as you scale. It unifies accounting, ERP, and real-time reporting for finance, retail, logistics, tech, and professional services. With payback in under six months and up to 250% ROI, and eight years as the customer-satisfaction leader, Sage Intacct helps you take control of your growth: Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit and schedule a demo. Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit to learn more. Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at — LINKS: Blake on LinkedIn: Docusign: CJ on LinkedIn: Mostly metrics: — RELATED EPISODES: "Steal Your Boss's Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth — TIMESTAMPS: 00:00:00 Preview and Intro 00:02:39 Sponsors – Fidelity Private Shares | Sage Intacct | Mercury 00:05:09 DocuSign as a Top CFO Tool 00:07:33 From E-Signature to Intelligent Agreement Management 00:09:09 Complexity Before and After a Signature 00:11:02 Cost of Poor Agreement Management 00:12:30 Agreement Oversight and CFO Risk 00:13:28 Pricing: Usage to Seat Models 00:14:12 Enterprise vs SMB Pricing 00:15:00 Sponsors – RightRev | Tipalti | Aleph 00:19:18 Simplicity, Tiers, and IAM Value 00:20:36 Forecasting New Products in a Renewals Base 00:22:13 Modeling Mix Shift and GTM Enablement 00:23:56 Faster Time-to-Value With Intelligent Repositories 00:25:06 Building GTM Muscle for a Platform 00:26:29 Launching IAM in Commercial First 00:27:31 Forecasting Growth vs Cost 00:28:41 Company-Wide Alignment on Priorities 00:30:02 Aligning Investor Messaging With Operations 00:31:20 Staying Focused on Long-Term Outcomes 00:32:27 Customer-First Decision Making 00:33:41 Transparency and What Not to Disclose 00:34:52 Asking Better Metric Questions 00:36:28 Avoiding Data Paralysis 00:38:52 Amazon’s Weekly Business Reviews 00:41:07 Bezos Meetings and the Silent Read 00:45:09 The “Question Mark Email” and Customer Anecdotes 00:50:22 Unit Economics of a Server and Early AWS Bets 00:53:42 Handling Nonpayment Risk 00:55:07 Operational Chaos: Perishables and Regulation 00:57:04 The “No Eggs in California” Story 00:59:31 Treating Escalations as Company Problems 01:00:59 Biggest Career Mistake 01:02:44 Advice to His Younger Self 01:06:34 Tools Finance Uses: Oracle, Bots, IAM, Salesforce, Workday 01:09:21 Wildest Expense Attempts 01:12:32 Closing Thanks and Credits #runthenumberspodcast #docusign #cfoinsights #saasleadership #aimanagement