Outbound Kitchen - B2B Sales Podcast

Jay Glenn, founder and CEO of Jay Glenn Agency who builds financially sustainable SDR programs. He discusses SDR P&L calculators and the 9-month to 18-month payback reality. Topics include efficiency benchmarks, the $50K ACV threshold, when to hire SDRs versus invest in product, headcount gap modeling, and separate conversion rates for inbound vs outbound.

⁠⁠⁠⁠📫 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

Troy Johnson, the SDR Enablement Program Manager at JumpCloud, shares his insights on building robust SDR enablement strategies. He discusses the vital distinctions between skills coaching and management roles. Troy reveals how he ramped up in just 90 days by interviewing over 15 leaders and leveraging AI for pattern recognition. He emphasizes three essential components for an SDR playbook, ideal onboarding structures, and the importance of timing when hiring for enablement. His use of AI in training is revolutionary, making rapid learning for sales reps a reality.

Jason Bay, Founder and CEO of Outbound Squad, shares insights from his extensive experience training companies like Shopify and Zoom. He reveals that effective cold calling is still alive, despite the average call lasting only 80 seconds. Discover his compelling cold calling framework, emphasizing customer problems over product pitches, and techniques that can drastically improve meeting show rates. Bay stresses the importance of habit-building in sales and how top reps leverage customer language to enhance engagement.

Want the prompt I used for this test?And my AI Prompt Library with 30+ outbound prompts?Upgrade now in my newsletter here.--We’re back. I tested 6 AI models head-to-head (including the two newest) for account research so you can pick the best.- GPT-5 Thinking (NEW)- Claude Opus 4.1 (NEW)- ChatGPT o3 (Previous winner)- Gemini 2.5 Pro- Grok 4- Perplexity Deep ResearchFull breakdown:https://newsletter.outbound.kitchen/p/i-tested-gpt-5-and-opus-41-for-account--Chapters:(00:00) Previous results & new models(03:15) ChatGPT-5 Thinking(06:43) Claude Opus 4.1(09:15) ChatGPT o3(11:25) Gemini 2.5 Pro(13:48) Grok 4(16:12) Perplexity Deep Research (19:12) Rankings & Recommendations

Teddy Frank, an impressive Ex-Senior SDR at Atrium, has mastered the art of cold calling, boasting a remarkable 27.8% conversion rate for meetings. In this engaging conversation, he shares his unique outbound sequences and effective cold-call strategies that garnered him a record-setting 77 meetings in a single quarter. Teddy emphasizes the importance of tailoring pitches for different company sizes and utilizing analytics to refine outreach efforts. His insights on handling objections and structured follow-ups are invaluable for sales professionals aiming to boost their success rates.

Unlock the secrets of efficient research with Perplexity AI! Discover why it's a better choice than GPT or Google for B2B outbound strategies. Learn practical tips and common pitfalls when using this tool. Dive into real-world examples, like researching private companies and the nuances of analyzing public firms. Enhance your account planning and prospect engagement with cutting-edge techniques that streamline your sales approach.

Tito Bohrt, CEO of Altisales, has built over 70 SDR teams, generating more than $100M in revenue. He shares his three pillars for successful sales development: targeting, outreach health, and messaging. Explore how personalized outreach and multi-channel strategies enhance connection rates. Tito dives into optimizing lead distribution and the importance of understanding buyer personas. He also reveals the pivotal lessons from three influential sales books that shaped his career, emphasizing continuous learning and adaptation in the evolving sales landscape.

Harry Sims, an outbound sales expert with over a decade of experience, shares his 10 essential rules for successful outbound sales. He emphasizes the balance between autonomy and structure for sales teams, noting the limitations of conventional playbooks. The discussion also covers the importance of understanding buyer personas, effective targeting techniques, and the role of emotional messaging in outreach. Additionally, Harry highlights innovative methods for gathering customer insights and the adaptability required in sales development.

Matt Roberts, Head of Sales Development at Mosaic (acquired by HiBob), shares his expertise in building a thriving outbound sales team from scratch. He discusses defining the Ideal Customer Profile (ICP) through customer insights and prioritizing accounts for better rep performance. Matt emphasizes the importance of effective messaging, leveraging automation, and adapting workflows as the team grows. His insights on balancing AI tools with personal touches in outreach reveal the secret to successful cold outreach in a competitive landscape.