Show notes
📫 Subscribe to the Outbound Kitchen newsletterAsk: Submit your questions here (anonymous)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 SDRs — and the 4 reasons handoffs killed velocityThe General Manager model: how city-level ownership created a "general manager of revenue" mindsetThe 3 pillars for scaling outbound infrastructure: data, tooling, and cultureAccount scoring when your data isn't perfect: why "just start somewhere" beats waiting for accuracyHow 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 onboardingBuilding rep-centric infrastructure: minimizing CRM fields and reducing tool sprawlConnect with Diane:https://www.linkedin.com/in/diane-ring/When you're ready👨🍳 Want to work with me? Send me a DM---Connect with me📌 Connect on LinkedIn📹 Subscribe on YouTube 🐦 Connect on X 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



