
From Amazon to Docusign: A CFO’s Guide to Building Durable Systems | Blake Grayson
Run the Numbers
Evolving from e-signature to IAM
Blake outlines Intelligent Agreement Management and the need to educate customers beyond signature.
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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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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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
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