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.
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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 https://www.fidelityprivateshares.com 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: https://bit.ly/3Kn4YHt
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 https://www.mercury.com
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 https://www.rightrev.com 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 https://www.tipalti.com/runthenumbers to learn more.
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LINKS:
Blake on LinkedIn: https://www.linkedin.com/in/blake-grayson-3197043/
Docusign: https://www.docusign.com/
CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/
Mostly metrics: https://www.mostlymetrics.com
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RELATED EPISODES:
“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth
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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
