E43: Geraldine MacCarthy, CRO of Oyster HR, Demystifies Distributed Sales Teams

Remote sales leadership is anything but one-size-fits-all. Geraldine MacCarthy, CRO at Oyster and former CRO at Personio, unpacks the complexities of building and scaling distributed sales teams across multiple continents. With deep experience at Google, Dropbox, and leading remote-first businesses, she reveals why the rigid remote vs. office binary misses what’s really happening—and what works.

She also challenges common beliefs about onboarding and coaching remote reps, sharing how enabling managers to own “last mile” enablement drives real performance impact.

Thanks for tuning in! New episodes of The Revenue Leadership Podcast drop every Wednesday.

Don’t miss GTM2025 — the only B2B tech conference exclusively for GTM executives. Elevate your 2026 strategy and join us from September 23 to 25 in Washington, D.C. Use code TOPLINE for 10% off your GA ticket.

Stay ahead with the latest industry developments and emerging go-to-market trends with Topline Newsletter by Asad Zaman. Subscribe today.

Tune into Topline Podcast, the #1 podcast for founders, operators, and investors in B2B tech hosted by Sam Jacobs, AJ Bruno, and Asad Zaman.

You’re invited! Join the free Topline Slack channel to connect with 600+ revenue leaders, share insights, and keep the conversation going beyond the podcast!

Key Chapters:

(00:00) - Introduction to Geraldine McCarthy and the Challenges of Scaling Distributed Sales Teams
(02:00) - Key Skills for Leading International Markets and Remote Teams
(05:00) - The False Binary: Debunking Myths About Remote Versus In-Office Work
(09:30) - Frameworks for Deciding When and Where to Co-Locate Sales Functions
(13:00) - Building Infrastructure and Norms for Successful Distributed Sales Organizations
(17:30) - Communication Best Practices for Distributed Revenue Organizations
(22:00) - Remote Working Norms: Setting Expectations Around Availability and Response Times
(27:30) - Trust Building in Remote Revenue Teams: ‘Work With Me’ Documents and Radical Candor
(33:00) - The Power of Written Communication and Documented Processes in Remote Organizations
(38:45) - Overcoming Common Remote Enablement Challenges with Intentional Coaching and Structure
(44:30) - The Critical Role of Frontline Leaders in Driving Enablement and Accountability
(48:30) - Measuring Manager Participation in Coaching and Sales Calls for Remote Success
(53:00) - Common Misconceptions About Remote Sales Onboarding and Performance
(58:00) - When Remote Sales Teams Thrive Versus When Co-Location Makes a Difference
(01:03:00) - Core Principles for Sales Enablement Programs That Move the Needle
(01:08:00) - Partnering Enablement With Product Marketing for Streamlined GTM Execution
(01:12:30) - Leadership Advice: Prioritize Learning, Radical Candor, and Trust as Foundations
(01:16:30) - Final Reflections and The Need for a New Paradigm in Workforce Models
(01:18:00) - Outro and Resources