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.

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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

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

The Revenue Leadership Podcast with Kyle Norton