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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“Steal Your Boss’s Job”: Calendly CFO John McCauley on Leadership, Ownership & Growth

https://youtu.be/VRpTNDIfzPY

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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

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

From Amazon to Docusign: A CFO’s Guide to Building Durable Systems | Blake Grayson

Run the Numbers