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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

Connect with Diane:

https://www.linkedin.com/in/diane-ring/

When you're ready

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Timestamps:

(00:00) Introduction

(00:52) Joining DoorDash: The Early Days

(03:18) Growth and Expansion

(04:38) Outbound Sales Strategy

(06:05) Field Reps and General Managers

(11:32) Data and Tooling for Sales

(17:00) Strategy and Operations

(23:01) Account Scoring and Market Segmentation

(28:12) Evolving Outbound Team Structure

(31:13) Navigating International Expansion

(32:33) Challenges in Different Markets

(36:26) Empathy in Sales Leadership

(40:07) Leveraging AI in Sales

(44:48) AI Tools for Sales Efficiency

(51:09) Consolidating Tech Stacks

(57:23) Future of AI in Sales