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

Sales efficiency isn’t just a buzzword—it’s the razor-edge that separates thriving GTM organizations from the rest. Tom Hanrahan, EVP and Global Head of Sales at Square, shares ten years of hard-earned insights on building lean, specialized sales teams that don’t just grow—they grow profitably. Hanrahan breaks down how obsessing over every dollar invested, from quota modeling to lead distribution, shapes a more sustainable and scalable revenue machine. He challenges the common trap of "more reps means more revenue," revealing why oversized teams often hide inefficiencies and create churn risks. Instead, he emphasizes smart specialization, rigorous data-driven segmentation, and maintaining a tight balance between lead volume and rep capacity.

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 of Tom Hanrahan and Today’s Sales Efficiency Focus
(02:56) - Defining Sales Efficiency: Balancing Growth and Profitability
(04:33) - Why Large Sales Teams Often Breed Inefficiency
(06:48) - Early Career Lessons That Shaped Hanrahan’s Sales Philosophy
(09:24) - Cultivating Patience to Build Foundations Amid Growth Pressures
(12:46) - Core Sales Efficiency Metrics: Quota Modeling, Lead Efficiency, and Specialization
(14:06) - How to Approach Quota Modeling to Maximize Capacity and Win Rates
(17:00) - Reframing the Mental Model: Opportunity Volume as the Real Bottleneck
(18:32) - The Underrated Power of Sales Team Specialization and Segment Focus
(22:59) - The Risks of Over-Specialization and Sales Org Brittleness
(27:02) - Modeling Sales Team Growth with Churn and Ramp Dynamics
(30:42) - Incubation Pods: Experimenting with Sales Motions Under Controlled Conditions
(33:56) - Metrics to Evaluate Before Committing to Sales Team Reorganizations
(36:43) - Hidden Inefficiency Drivers: Frontline Manager Consistency & Lead Weighting
(40:00) - The Value of Weekly Business Reviews to Maintain Rigor and Transparency
(44:18) - Deep Data Analysis Culture: Finding Gaps by Embracing Hard Truths
(47:01) - Current Team Structure at Square: Vertical Specialization and Channel Diversity
(48:58) - Recalibrating Incentives and Focus: Driving New Business Growth vs. Farming
(50:50) - Fine-Tuning Inbound vs. Outbound Mix to Enhance Sales Productivity
(52:43) - The Concept of “Sweet Spot” Targeting for Optimal ROI on Sales Efforts
(55:30) - Full Cost Modeling: Loading All Expenses to Reveal True Unit Economics
(56:14) - Building Efficient Revenue Organizations from the Ground Up: Why Entry-Level Talent Matters
(58:30) - Identifying Ideal Sales DNA: Coachability, Competitiveness, Hard Work, Motivation
(01:02:30) - Assessing Motivation and Hard Work During Hiring to Weed Out Misfits
(01:06:40) - Leveraging Data Science in Hiring: Scorecard Retro and Pattern Recognition
(01:12:00) - What Makes a Great Revenue Leader: Balancing Operational Mastery and People Skills
(01:13:15) - Advice for New Sales Leaders: Get Curious Before Acting on Presumptions
(01:14:20) - Navigating Cross-Functional Dependencies: The Enterprise Sales Parallel
(01:17:39) - Personal Reflections: The Enduring Lesson from Hanrahan’s Father on Commitment and Grit

AI is transforming go-to-market operations—and at Canva, it's not just a trend, it's a mandate.

In this episode, Jessica Chiew, Head of GTM Operations and Strategy at Canva, joins Kyle to break down how her team is leading AI adoption across a 5,000-person organization. She shares how Canva blends centralized support with functional ownership, why they created a dedicated GTM AI Lead role, and how they prioritize use cases that deliver real business impact. Jessica and Kyle also dig into the realities of build vs. buy decisions, how to avoid tool sprawl, and why every GTM leader needs to be hands-on with AI.

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) - Jessica Chu’s GTM AI Transformation Journey at Canva Begins

(02:48) - The Most Exciting Time in Ops: Creativity and Existential Dread

(04:30) - From Vendor Fatigue to AI Enthusiasm: Renewed Curiosity in Tooling

(06:59) - Early Days of AI Momentum at Canva

(09:30) - Making AI Transformation Everyone’s Job

(11:45) - Defining the Role: GTM AI Lead and Workflow Innovation

(14:25) - The Changing Nature of Data Ops in AI-Powered Sales

(16:50) - How Canva Organizes AI Transformation: Central Council vs. Functional Innovation

(18:29) - Cutting Through the Noise: Where to Start with AI in GTM

(21:00) - Why Data Quality Is the Prerequisite for GTM AI Success

(24:30) - Vendor Sprints and the Realities of Building vs. Buying AI Solutions

(29:00) - Execution as the Only Moat: Staying Ahead in the Commoditization Wave

(35:10) - Limiting Surface Areas: The Case Against Point Solutions

(38:30) - Balancing Experimentation with Simplicity for Field Teams

(41:51) - Organizational Change: Iterative Improvements vs. Big AI Bets

(46:45) - Hands-On Leadership and the Decline of Middle Management