Outbound Kitchen - B2B Sales Podcast

Hosted by Elric Legloire - The Outbound Chef

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May 2026

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Hey Chef, welcome to the Outbound Kitchen! I’m Elric Legloire, your host. The go-to podcast to scale outbound, and turn it into your #1 growth engine. - Cold calls, emails, and social selling. - Building, hiring, and scaling outbound teams. - Creating an outbound motion from scratch. - Using AI to optimize outbound. The goal? A predictable outbound pipeline for your B2B SaaS business. Tune in for solo episodes, interviews, AMAs, and chats with B2B SaaS and GTM leaders. outboundkitchen.substack.com

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May 15, 2026Episode 3116 min

OK31: Corporate Gifting: A 2-Step ABM System for Tier-1 Accounts & Prospects

Get the 3 prompts (research + classify, gift ideas, note writer) in my paid newsletter here.---In this episode, I break down the 2-step ABM gifting system you can run on your top 200 accounts. How to find the clue. How to classify the prospect into one of four buckets (Identity, Passion, Milestone, or No Gift). How to pick a gift that maps to the specific niche. And how to write the note that proves the research wasn't AI-generated.--If you're new here, I'm Elric Legloire, founder of Outbound Kitchen. I help B2B SaaS companies between $2M and $50M ARR fix and scale their outbound system. My view: in 2026, productivity is the multiplier to scale outbound teams.Menu:- Why a $300 researched gift is cheaper than the cold email sequence you'd run into a $200K to $1M ARR account- The 4-bucket prospect classification: Identity, Passion, Milestone, No Gift (and why ~70% land in No Gift)- The specificity ladder: vague vs. niche vs. Passion vs. Signature clues, and which two qualify for a gift- Where to find Signature clues: LinkedIn About sections, podcast appearances, keynotes, blogs, book forewords- A worked example on Kyle Norton (CRO at Owner.com). From clue ("former MMA gym co-owner, black belt") to gift (personalized oak belt display from Etsy with his "Slow is smooth. Smooth is fast." quote)- The 5-part note template: research proof, rabbit hole, gift bridge, pitch + proof, soft ask- Why Perplexity beat ChatGPT for clue research this round, and why you should keep benchmarking AI modelsReferenced:- Stevie Case (CRO, Vanta), Quake rocket launcher gift, sent by Brennan- Tom (CMO, Incident.io), signed vinyl gift- Newsletter with the 3 prompts (research + classify, gift ideas, note writer): https://newsletter.outbound.kitchen/p/abm-how-to-gift-your-top-200-accountsChapters(00:00) Why Gifting Works(01:37) ABM Outbound Fit(02:41) Step One Find Clues(03:29) Clue Buckets Framework(04:41) Avoid Creepy Research(05:38) Make Clues Specific(06:55) Where To Research(07:17) Kyle Norton Example(09:51) Decision Tree Choices(10:40) Step Two Gift Ideas(11:56) Personalized Gift Build(13:24) Write The Note(14:58) Note Template--When you're ready⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Want to work with me? Send me a DM⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ---Connect with me⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 Connect on X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

April 26, 2026Episode 301 hr 6 min

OK30: How to Build a High-Performing Outbound Team in 2026 (Elric Legloire on Cognism's Prospect Podcast)

⁠⁠⁠⁠Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---This episode was originally recorded in French for Cognism's Prospect podcast with Laetitia Fall. The English audio you're hearing is an AI-translated dub generated with ElevenLabs. Original French version: https://youtu.be/DMRO_GGp-1A--If you're new here, I'm Elric Legloire, founder of Outbound Kitchen. I help B2B SaaS companies between $2M and $50M ARR boost their outbound results. My view: in 2026, productivity is the multiplier, not headcount. --We discuss:- Why outbound isn't dead, but pipeline got roughly 10x more expensive (1% conversion in 2015 to needing 1,000 emails per opportunity in 2023, source: Winning By Design)- Why global SDR headcount grew over 20% in a year while public layoffs dominated the LinkedIn feed- The Owner.com benchmark: 40 appointments per BDR per month, 25% close rate, $70-80K sourced revenue per BDR per month- When to hire experienced SDRs vs juniors, and the 12-meetings-per-month threshold that signals your playbook is ready- Why ICP work beats tool selection (Tier 1 closes at 25%, Tier 2 at 5%, you need 5x the volume to compensate)- Snowflake's 140 ICP data points and why 10-15 is the realistic target for most teams- Multichannel orchestration when only 30% of your prospects are reachable on LinkedIn- The data-quality test most teams skip: coverage rate per persona, per market- AI in outbound (January 2026): what actually works, why most LinkedIn AI messages fail, and the foundation AI needs (market, CRM, message principles, signals)Referenced:Outbound Kitchen newsletter: https://newsletter.outbound.kitchenElric Legloire on LinkedIn: https://www.linkedin.com/in/elriclegloire/Cognism's original French episode: https://youtu.be/DMRO_GGp-1AHost: Laetitia Fall Sources cited in episode: Winning By Design, Insight Partners (Jeremy Donovan's portfolio data), Owner.com BDR benchmarks, Snowflake ICP methodology----When you're ready⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Want to work with me? Send me a DM⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Connect with me⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 Connect on X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠----Chapters:(00:00) Outbound Crisis 2026(00:11) Podcast Setup and Dub(02:39) Is Outbound Dead(05:46) Why Conversion Fell(09:43) Stop Hiring Juniors First(12:49) SDR Growth vs Layoffs(18:13) When to Hire and Scale(25:02) Who Should Manage SDRs(27:17) Start With ICP First(29:50) How to Define ICP(34:34) Intent Signals vs ICP(35:28) Managing Account Batches(36:43) ICP Evolves With Product(39:14) Who Owns the ICP(41:45) Experimenting New Markets(42:50) Defining ICP Subsegments(44:48) Real Multichannel Outreach(47:18) Orchestrating Channels(49:20) Writing Better Messages(53:02) Data Quality Over Tools(55:55) Testing AI Market Research(59:31) When to Hire RevOps(01:01:40) AI Outbound Workflows

April 19, 2026Episode 299 min

OK29: 13 episodes + newsletters I shipped in Q1 (+ what's coming)

You can read the written version of this episode here: https://newsletter.outbound.kitchen/---Q1 recap, Q2 roadmap, and the three systems I'm building for outbound teams right now. Everything I shipped in Q1:March 2026- OK28: How ElevenLabs is Scaling Outbound From 5% to 46% With Human SDRs: https://newsletter.outbound.kitchen/p/how-to-scale-outbound-from-5-to-46- Best AI for Account Research? I Tested 7 AI Models: https://newsletter.outbound.kitchen/p/best-ai-for-account-research-i-testedFebruary 2026- I tracked 232 outbound teams. Here's what I found: https://newsletter.outbound.kitchen/p/the-outbound-paradox-reality-vs-linkedin- OK26: 5 AI Cold Call Training Scenarios Every Outbound SDR Team Should Run: https://newsletter.outbound.kitchen/p/how-to-train-cold-callers-with-ai- ClickUp built THIS before scaling dials: https://newsletter.outbound.kitchen/p/clickup-built-this-before-scaling- 9 ways I use Claude Code for outbound: https://newsletter.outbound.kitchen/p/ive-been-using-claude-code-sinceJanuary 2026- OK25: How to Build a Profitable Outbound SDR Team: https://newsletter.outbound.kitchen/p/how-to-build-a-profitable-outbound- How to prove outbound is working (to your CEO): https://newsletter.outbound.kitchen/p/how-to-prove-outbound-is-working- OK24: How DoorDash Scaled Outbound from $291M to $8.6B: https://newsletter.outbound.kitchen/p/how-doordash-scaled-outbound-from- How to Divide Your Outbound Market Into Territories (7-Step Guide): https://newsletter.outbound.kitchen/p/how-to-divide-your-outbound-market- OK23: How to Build SDR Enablement from Scratch: https://newsletter.outbound.kitchen/p/how-to-build-sdr-enablement-from- 100 emails → 1 meeting (2015). Now it's 1,000+: https://newsletter.outbound.kitchen/p/100-emails-1-meeting-2015-now-its- OK22: How to Cold Call for Higher Connect Rates: https://newsletter.outbound.kitchen/p/how-to-cold-call-for-higher-connect---Who I am? Elric Legloire, founder of Outbound Kitchen. 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Chapters(00:00) Q1 Recap Setup(00:21) March Highlights(01:13) February Highlights(02:36) January Highlights(04:04) Q2 The Pantry Launch(04:57) New Systems and Automations(06:27) Pricing and Subscriber Notes(07:03) Podcast Guest Lineup(07:41) Q2 Newsletter Topics(08:41) Data Benchmark Help

March 17, 2026Episode 2852 min

OK28: How to Scale Outbound From 5% to 46% With Human SDRs, No Standups, and an AI-Native Operating System - Jonathan Chemouny, GTM at ElevenLabs

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Jonathan Chemouny is GTM at ElevenLabs, where he scaled outbound from 5% to 46% of pipeline in one year with a small distributed SDR team. He previously built and led SDR teams at Intercom and Lattice. His team operates with no job titles, no standups, and no activity metrics , running on async Slack communication and trust-based autonomy.We discuss:- Why an AI-native company at 95% inbound decided to build a human SDR team instead of automating everything- How ElevenLabs defines outbound (pure cold + PLG-assisted) and why the distinction matters for pipeline math- Why candidates from finance and VC outperform career SDRs -- and the hiring process that screens for it- The operating system: no standups, no pipeline reviews, no job titles, async Slack ("Slack militaire")- How SDRs run demos, travel to meet prospects in person, and attend events solo -- one rep skipped President's Club for CCW Berlin and came back with 60+ SQOs- The AI SDR handling inbound qualification in multiple languages with 78% decisions requiring no human intervention- WhatsApp as a prospecting channel in Europe and why LinkedIn outperforms emailReferenced:- Carles Reina on 20VC (20x Base-to-quota model)- Jonathan Chemouny on LinkedIn: linkedin.com/in/chemouny/- ElevenLabs: elevenlabs.io----When you're ready⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Want to work with me? Send me a DM⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Connect with me⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 Connect on X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠----Chapters:(00:00) Welcome and Setup(00:25) Why Hire SDRs in AI(01:45) Inbound to Outbound Shift(02:33) Defining Outbound and Pipeline(04:02) Talent Profile and Culture(06:21) No Titles and Global Hiring(07:42) Fast Interview Process(11:32) Testing AI Fluency(13:43) Roleplay and Sequence Review(15:19) Career Paths and SDR Role(18:52) Enabling Non Sales Hires(19:47) Productivity and Outbound Mix(24:42) Full Cycle AE Debate(26:05) Culture Intensity and Remote(28:05) Cutting Meetings with Slack(28:57) Slack Notes Automation(29:27) Coaching On The Road(30:47) Incentives And Outbound Shift(31:42) Modern Qualification And Handoffs(33:50) Pipeline Metrics Dashboard(34:40) SDRs In The Field(38:03) SDRs Running Demos(41:02) AI Outreach Demos(41:22) AI Tools And Inbound Agent(44:44) Iteration And Focus Lessons(46:24) Cold Calling And WhatsApp(49:49) KPIs And Agent SDR Debate

March 3, 2026Episode 2712 min

OK27: Best AI for Account Research? I Tested 7 AI Models - March 2026 benchmark

Want the prompt I used for this test? And my AI Prompt Library with 30+ outbound prompts?⁠Upgrade now in my newsletter here.-I tested seven AI models on the same account research prompt, 12 specific instructions, one target company (Replit), one buyer lens (TrackRec). This is my March 2026 benchmark.The models: Perplexity Sonar, GPT 5.2 Thinking, Grok 4.2 Beta, Grok 4, Claude Opus 4.6, Claygent (Argon), and Gemini 3 Pro. I scored every model on six weighted criteria, tracked which instructions each model actually completed, classified why they missed what they missed, and manually verified every disputed claim.Agenda:- Why I expanded from 3 scoring criteria to 6 — and how adding Business Relevance changed the rankings- What instruction completion reveals that scores alone don't (Perplexity: 10/12, Gemini: 1/12)- The difference between hallucinations and false claims — and why it matters for automation at scale- Why four models found September funding and stopped looking (the persistence failure pattern)- The $400M funding round that may or may not be real — REPORTED vs VERIFIED as a new verification category- Which model to use for high-value accounts vs volume enrichment in Clay- Web app vs API vs Clay: why your results will be different and what I'm testing in the next benchmarkReferenced:- TrackRec: https://www.trackrec.co- Replit: https://replit.com- Perplexity: https://www.perplexity.ai- Clay: https://www.clay.com- RepVue: https://www.repvue.com- The account research prompt: Available for Outbound Kitchen paid members-Who I am? Elric Legloire, founder of Outbound Kitchen. 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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠-Chapters:(0:00) - Why I keep benchmarking AI models(1:45) - The test setup: TrackRec researching Replit(3:00) - What changed from the last test(6 criteria, instruction tracking)(3:30) - The new rankings(4:05) - Perplexity: VP of SDR, podcast, RepVue miss(5:00) - GPT 5.2: zero false claims, Glassdoor depth(5:30) - The $400M funding round — is it real?(7:00) - Grok 4.2: 56 seconds, best RepVue data(8:00) - Bottom four models (quick summary)(8:55) - Verification: hallucinations vs false claims(10:05) - Which models I recommend(10:45) - Web app vs Clay availability(11:30) - What's next

February 20, 2026Episode 2650 min

OK26: How to Train Cold Callers with AI: 5 Scenarios That Took JumpCloud from 10 Reps to 100+ - with Troy Johnson, SDR Enablement at Jumpcloud

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)-Troy Johnson is the SDR Enablement Program Manager at JumpCloud, where he runs the SDR Enablement program for the Americas. He has over eight years in sales development, including six years managing SDR teams. This is his second appearance on the show, Part 1 covered SDR enablement foundations, and Part 2 dives into practical AI role-play implementation. We discuss:- How JumpCloud uses AI role-play to certify SDRs during onboarding -- 100+ practice scenarios before going live- Running a March Madness-style qualification competition to drive AI adoption and peer coaching- The monthly rhythm for rolling out updated talk tracks with live practice and manager demos- Using Gong's theme spotter to identify the most common objections and build targeted AI drills- Building an SDR-to-AE progression program with AI scenarios aligned to AE managers- Why managers should practice AI role-play themselves to lead by example- Tools used: Hyperbound, Orum, Gong, and ChatGPT Voice Mode as a free alternativeReferenced:- Hyperbound: hyperbound.ai- Orum: orum.com- Troy Johnson on LinkedIn- Gong- ChatGPT-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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠-Chapters:(00:00) Intro(00:44) Framework: Building a World-Class Outbound Team (Talent, Productivity, Enablement) (02:18) Why JumpCloud Went All-In on AI Role Play (Phone-Heavy Motion) (03:56) Scenario #1: Onboarding Certification with AI Call Practice (06:31) How Call Academy Works + Certification Criteria & Rubric Scoring (09:17) Results & Benefits: 10x Reps, Faster First Meeting, Multilingual Coaching (11:46) Scenario #2: Qualification Competition (Gamified Tournament for Adoption) (14:39) How the Tournament Runs: Schedule, Scoring, Tools (Orum vs Hyperbound) (18:50) Scenario #3: Talk Track Adoption—Rolling Out Updates with Live AI Practice (22:05) Measuring Adoption + Handling Common Objections (Setup for Next Scenario) (24:15) Test Talk Tracks with Top Performers + AI Role Play Before Rollout (25:51) Scenario #4: Weekly Objection-Handling Drills That Build Confidence Fast (28:15) Pick the Right Objections: Use Gong Theme Spotter + Manager Alignment (30:07) Talk Tracks for “Not a Priority” + “Already Have a Solution” (Battlecards) (32:02) Competitor Tracking, Game Tape Reviews, and Managers Practicing Too (34:40) Scenario #5: Upskilling SDRs for the Next Role (SDR → AE and Beyond) (37:34) Designing the Progression Program: Mentorship, Shadowing, Practice, Certs (42:59) Data-Driven Enablement: Scorecards, “Beat the Bot,” and Individual Coaching (46:41) Tool Stack: Hyperbound, Orum, ChatGPT Voice Mode + How Gong Supports It (49:44) Wrap-Up: Start with One Scenario, Lead by Example, and Keep Iterating

January 29, 2026Episode 442 min

OK25: How to Build a Profitable Outbound SDR Team: P&L Math, Headcount Decisions, and the 9-Month Payback Reality with Jay Glenn, Founder at Jay Glenn Agency

Grab the SDR P&L Calculator⁠⁠⁠Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)Jay Glenn is the founder of Jay Glenn Agency, where he helps B2B companies build financially sustainable SDR programs. After witnessing mass SDR layoffs in 2022, Jay developed a suite of P&L calculators that have become essential tools for SDR leaders proving ROI to their executives.We discuss:- Why 2022 was the wake-up call for SDR financial accountability- The SDR P&L Calculator — walkthrough of inputs, outputs, and the 7.91x return benchmark- The $50K ACV threshold for sustainable SDR models (and why lower ACVs fail)- Customer lifecycle as the most underrated profit lever for SDR teams- When to hire SDRs vs. when to invest in product and full-cycle AEs- The Headcount Gap Calculator for modeling scale decisions- Why inbound and outbound need separate conversion rate assumptions- How to present SDR financials to your board (with or without good news)Referenced:- Jay Glenn on LinkedIn: https://www.linkedin.com/in/jayglenn/- Jay Glenn Agency: https://www.jayglenn.co/- RepView (SDR compensation data): repvue.com- Clay (market research): clay.com- TitanX (phone deliverability): titanx.comWhen you're ready⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠👨‍🍳 Want to work with me? Send me a DM⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Connect with me⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 Connect on X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Chapters: (0:00) The Importance of Financial Metrics in Sales(0:52) Realizing the Need for Financial Focus in Sales(2:07) Efficiency and Market Size Considerations(4:30) Leveraging Tools for Market Understanding(5:34) Evaluating SDR Teams: Common Mistakes and Solutions(7:26) Building and Using Financial Spreadsheets(10:37) Analyzing Historical Data and Future Planning(19:55) Scaling and Headcount Considerations(27:49) Outbound Strategies and Metrics

January 21, 2026Episode 359 min

OK24: How DoorDash Scaled Outbound from $291M to $8.6B with Full-Cycle Field Reps, City-Level Ownership, and No SDRs (with Diane Ring)

⁠⁠⁠⁠📫 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

January 15, 2026Episode 249 min

OK23: How to Build SDR Enablement from Scratch: When to Hire, What to Focus On, and the 3 Things Every Outbound Playbook Needs (with Troy Johnson, SDR Enablement at Jumpcloud)

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)---Troy Johnson is the SDR Enablement Program Manager at JumpCloud, where he supports three outbound and inbound teams across the Americas. After six years as an SDR manager, he transitioned into enablement and ramped himself up by interviewing 15+ enablement leaders externally and using AI to find patterns across the conversations. He now runs a bi-weekly peer group with other SDR enablement managers to share best practices.We discuss:1. What SDR enablement actually is, the difference between a "head coach" and a "skills coach"2. How Troy ramped himself up in 90 days by interviewing 15 enablement leaders and using AI to find patterns3. The three essential components every SDR playbook needs from day one4. How to split your time between content, coaching, and training (the 30/30/30 framework)5. When to hire your first SDR enablement person — team size, motions, and complexity signals6. The ideal onboarding structure: 2-3 weeks of foundations + "Prospecting Bootcamp" through day 607. Using AI to accelerate business acumen — the underrated use case most teams missConnect with Troy:https://www.linkedin.com/in/techsalestroy/--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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Chapters(0:00) Introduction to SDR Enablement(0:54) Defining SDR Enablement(3:02) The Importance of SDR Enablement(4:46) Onboarding and Training Strategies(5:18) Ramping Up in SDR Enablement(12:42) Day-to-Day Operations(17:05) Team Structure and Support(21:08) Scaling and Complexity in SDR Teams(24:46) The Role of Enablement in Sales Teams(25:44) Key Components of an SDR Playbook(30:11) Effective Onboarding Strategies(35:09) Leveraging AI for Sales Enablement(40:13) Metrics to Measure Enablement Impact(41:38) AI Tools and Techniques in Sales

January 8, 2026Episode 150 min

OK22: How to Cold Call for Higher Connect Rates, Better Conversations, and Meetings That Actually Show Up - with Jason Bay, CEO of Outbound Squad

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠---Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)---In this episode, Jason Bay, Founder of Outbound Squad, breaks down the art and science of cold calling in 2025.He shares data from training companies like Rippling, Shopify, and Zoom, revealing why the average cold call lasts just 80 seconds, and how top reps achieve 25%+ conversion rates while most struggle at 4.6%.Jason walks through his complete cold calling framework: the permission-based opener, reverse pitch, money questions, and the tactics that drive 75-80% show rates. His candid breakdown of what separates average reps from top performers, backed by Gong data from 100K+ calls, provides a masterclass in modern cold calling.-3 biggest takeaways:- Lead with problems, not product: problem-based language gets 3x more meetings than product pitches- The habit matters more than the outcome: build the weekly rhythm before optimizing the talk track- Customer voice over product voice: steal language directly from sales calls and discovery conversations-Who is Jason Bay?Founder of Outbound Squad, cold calling trainer for companies like Rippling, Shopify, and ZoomConnect with Jason:- On LinkedIn: https://www.linkedin.com/in/jasondbay/- Outbound Squad: https://outboundsquad.com-Key stats from this episode:- Average connect rate: 5.4% (top reps hit 13-15%+)- Average conversion rate: 4.6% (top reps hit 20-35%)- Average show rate: 56% (top reps hit 75-80%)- Rippling sources 50% of pipeline from outbound cold calling- Problem-based language: 16% success vs 5.5% for product pitches---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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠---Chapters:(00:00) Episode Overview(01:13) Is Cold Calling Dead?(01:57) Cold Calling Effectiveness and Statistics(03:29) Challenges and Strategies in Cold Calling(05:31) The Importance of Relevance and Offers(08:12) Effective Cold Call Openers(13:05) Reverse Pitch and Problem-Based Language(18:28) Tailoring Cold Calls to Different Brands(19:54) Leveraging Customer Language and Patterns(24:52) Building a Weekly Rhythm for Outbound Success(25:59) Creating a Coaching Culture(27:03) Granular Coaching for BDRs(28:15) Improving Call Metrics(30:59) Data Accuracy and Provider Evaluation(34:31) Top Reps and Their Techniques(41:04) Incorporating AI in Sales Training(46:34) Non-Negotiable Cold Calling Principles