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Diane Ring led B2B strategy and operations at DoorDash from 2018 to 2023, joining when the company had ~500 employees and $291M in revenue, and leaving post-IPO with 15,000+ employees and $8.6B in revenue. She was on the leadership team for Merchant Strategy & Operations, where she helped scale the sales team from ~200 reps to thousands across North America and international markets. Most recently, she was Sr. Director of Sales Ops at TouchBistro, leading strategy and ops for a 100+ person GTM organization.

We discuss:

Why DoorDash used full-cycle field reps with no SDR handoffs — and the 4 reasons handoffs killed velocity
The General Manager model: how city-level ownership created a "general manager of revenue" mindset
The 3 pillars for scaling outbound infrastructure: data, tooling, and culture
Account scoring when your data isn't perfect: why "just start somewhere" beats waiting for accuracy
How to adapt outbound playbooks for international expansion (and why US vendors often fail in Canada)
AI coaching in practice: real-time monologue alerts, post-call scorecards, and AI roleplay bots for onboarding
Building rep-centric infrastructure: minimizing CRM fields and reducing tool sprawl