How to scale your career from SDR to leadership: Mike Stevenson

Want to learn how to scale your sales career alongside a fast-growing company?

Looking for real advice on navigating the path from SDR to AE to sales leadership?

Mike Stevenson from DocuSign shares his playbook for building a successful sales career over nearly two decades, including how he's scaled himself through 11 years at one company.

Mike has led teams across the full spectrum—from SMB to Enterprise, from individual contributors to sales development reps, spanning North America and EMEA. He's had a front-row seat to DocuSign's evolution from the world's leading e-signature point solution to a comprehensive Intelligent Agreement Management platform.

We covered:

• Scaling with your company: How to evolve your skills and role as your company grows and changes
• Career progression secrets: The early advice that helped Mike build his sales career over two decades
• Prospecting mastery: Why prospecting is art vs. science, and how the approach differs for AEs vs. SDRs
• SDR to AE transition: What it really takes to make the jump to Account Executive in 2025

About Mike

With nearly 2 decades of sales experience ranging from SMB to Enterprise, Mike has led teams of both full sales cycle Account Executives and Sales Development reps across North America and EMEA. Currently, Mike leads the Docusign Majors teams in the evolution of Docusign from the world's leading e-Signature product—which was more of a point-solution, demand-plan based sale—to a platform sales motion with their Intelligent Agreement Management solution.