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Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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 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

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠👨‍🍳 Want to work with me? Send me a DM⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Connect with me

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 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

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---

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 patterns

3. The three essential components every SDR playbook needs from day one

4. 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 signals

6. The ideal onboarding structure: 2-3 weeks of foundations + "Prospecting Bootcamp" through day 60

7. Using AI to accelerate business acumen — the underrated use case most teams miss

Connect 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

⁠⁠⁠⁠📫 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 Zoom

Connect 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

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 Research

Full 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

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

--

In this episode, we'll discuss:

- The different outbound sequences Teddy uses

- His cold-calling framework

- How to use your analytics and reports to improve your results

Teddy Frank was a top-performing SDR @ Atrium

Teddy set a record for the most outbound meetings booked in a quarter (Q1 - 77 meetings). In Q1, he booked 50 meetings via cold calling, with a conversation-to-meeting booked rate of 27.7%.

Connect with Teddy on LinkedIn

⁠https://www.linkedin.com/in/teddy-frank-690b501b7⁠

Here’s a bit more info about Teddy's accounts and buyer personas:

- Personas -> 2nd Level+ Sales and RevOps Leaders (occasionally SalesDev)

- Industries -> Software Development, IT Services / Consulting, Computer / Network Security

- Org Size -> 51+ folks in sales org (ranges from 300 - 10k employees)

----

📬 For more prospecting and sales development tips, join 3,911 SDRs getting the SDR Game newsletter here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://sdrgame.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with me on LinkedIn: Elric Legloire ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/elriclegloire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

----

Chapters

(00:00) Top SDR

(03:54) Defining Top Tier Accounts

(07:18) Handling Objections and Referrals

(10:13) Call Calling Strategies for Booking Meetings

(11:10) Philosophy for Booking Meetings with Directors and VPs

(12:05) Structuring the Cold Call Pitch

(14:24) Using Relevant Statements and Assumptions

(15:22) Pain and Solution Statements in the Pitch

(18:47) Going for the Close in the Pitch

(20:15) Handling Objections and Sending More Information

(21:39) Asking for a Specific Follow-Up Time

(22:38) Handling Objections to Booking a Meeting

(25:05) Researching Prospects and Private Equity Companies

(26:30) Understanding the Challenges of Rev Ops Leaders

(28:59) Using Research to Improve the Pitch

(30:54) Using Analytics to Improve Conversion Rates

(32:50) Calling After 5 PM for Better Results

(40:59) Advice for New SDRs

Get full access to Outbound Kitchen at

⁠outboundkitchen.substack.com/subscribe

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

⁠Grab the prompts we used in this episode here https://elriclegloire.gumroad.com/l/PerplexityAIprompts

---

When you're ready

⁠⁠⁠📫 Subscribe to the newsletter⁠⁠⁠

⁠⁠⁠👨‍🍳 Want to work with me? Send me a DM⁠⁠

---

Connect with me

⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠

⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠

⁠⁠⁠🐦 Connect on X ⁠⁠

Chapters

(00:00) Overwhelmed by Research?

(01:04) 3 Reasons to Choose Perplexity Over GPT or Google

(02:02) How NOT to Use Perplexity

(02:55) Using Perplexity for Effective Account Research

(03:27) Example 1: Researching a Private Company (Nooks)

(10:30) Example 2: Researching a Public Company (Eventbrite)

Get full access to Outbound Kitchen at

⁠outboundkitchen.substack.com/subscribe

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

---

3 things you'll learn in this episode, the 3 pillars of successful sales development:

- Targeting

- Outreach Health

- Messaging

Tito Bohrt is the CEO of Altisales

Tito's results:

- Has built 70+ SDR teams from the ground up

- Sourced over $100M in revenue for his clients.

Connect with Tito: ⁠⁠https://www.linkedin.com/in/titobohrt/⁠

Looking for an SDR job? ⁠https://www.altisales.com/careers⁠

---

📬 For more prospecting and sales development tips, join 3,301 SDRs getting the SDR Game newsletter here: ⁠⁠⁠⁠⁠⁠⁠https://sdrgame.substack.com/⁠⁠⁠⁠⁠⁠

Connect with me on LinkedIn: Elric Legloire ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/elriclegloire/⁠⁠⁠⁠

---

Timestamps:

(0:00) Meet the CEO Behind 70+ SDR Team Success Stories

(0:54) Multichannel outreach: what’s working today

(2:16) Boosting SDR Team Connect Rates

(6:49) Crafting Precision: Account Targeting and Scoring Demystified

(11:57) Navigating Buyer Personas

(15:43) Unlocking Pain Points: Deciphering Prospect Challenges

(18:25) Lead Distribution Pitfalls: Two Missteps Costing You Big

(23:40) The Pulse of Effective Outreach

(25:11) The Ideal Number of Sequences

(27:55) When Should You Tweak Your Sequences

(30:46) Understanding Statistical Significance in Sales

(33:00) Reflection: Tito's Greatest Misstep in Messaging

(36:12) 3 Sales Books Transforming Tito’s What He Learned Sales Journey

(38:29) Tito's Evolution: what he learned from the Last 5 Years

(40:39) Empowering SDRs: Tips from the Frontline

Get full access to Outbound Kitchen at

⁠outboundkitchen.substack.com/subscribe

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

---

3 things you'll learn about outbound sales in 2024:

- The 10 rules of outbound

- What's working for Harry

- What I'm working on with outbound at a previous company

---

Harry Sims is the SDR Leader at Scratchpad.

Harry has been working in sales for the past 12 years and leading/building SDR teams for the past 7 years.

Connect with Harry on LinkedIn

⁠https://www.linkedin.com/in/outbound-works/

Subscribe to Harry's newsletter: ⁠https://www.personal-prospecting.com/⁠

---

📬 For more prospecting and sales development tips, join 3,712 SDRs getting the SDR Game newsletter here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://sdrgame.substack.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Connect with me on LinkedIn: Elric Legloire ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/elriclegloire/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Chapter

(00:00) Outbound sales expert

(01:24) The Limitations of Playbooks and the Need for Autonomy

(06:07) Educating Prospects and the Importance of the First Meeting

(07:34) Understanding the Prospect's Awareness and Education Level

(08:32) Targeting the Buyer and Business for Effective Outbound

(10:30) Using Lawsuits and Technographic Data for Targeting

(12:28) The Importance of Targeting in Outbound

(20:06) Generating Ideas for Messaging through Customer Feedback

(23:27) Gathering Insights from Customer Calls and Interviews

(26:49) Using Champion Data and Referrals for Targeting

(30:11) Tracking and Enriching Data for Effective Outbound

(32:32) The Experimental Nature of Outbound and the Future of Personalization

Get full access to Outbound Kitchen at

⁠outboundkitchen.substack.com/subscribe

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠

---

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

---

In this episode, Matt Roberts, Head of Sales Development at Mosaic, shares his journey of building an outbound sales team from scratch.

He discusses his approach to understanding the finance space, defining ICP, crafting effective messaging, and scaling to 10 BDRs.

Matt reveals how he managed executive expectations, prioritized accounts, and created systems that led to impressive results. His candid insights about what worked, what didn't, and what he'd do differently provide a masterclass in building high-performing outbound teams.

3 biggest takeaways:

- Define your own ICP through customer research

- Prioritization of accounts drives rep performance

- Phone skills remain critical for career advancement

---

Who is Matt Roberts?

Head of Sales Development at Mosaic (acquired by HiBob)

More context about the SDR team:

- ACV: $32k

- Industries:  B2B SaaS

- Buyer personas: finance leaders

- Markets: North America

- 2024: $2.6m ARR sourced from 7 fully ramped BDRs, $18.1m pipeline generated

- From 0 outbound at all to 2,300 meetings booked, and 1,800 opps created 3 years later

Connect with Matt:

- On LinkedIn⁠⁠⁠: https://www.linkedin.com/in/matthewpaulroberts5/

---

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) Matt Roberts and Mosaic's Success

(00:43) Matt's Initial Priorities at Mosaic

(02:19) Understanding the Market and Customers

(08:52) Defining and Refining ICP

(16:49) Managing Expectations with Leadership

(25:12) Unexpected Hiring Success

(27:56) Onboarding and Training Strategies

(31:56) Scaling the Team: Processes and Systems

(40:48) Leveraging AI in Sales

(45:01) Reflections and Future Improvements

⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠

---

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

---

Discover how Jesse Leong, a classical musician turned #1 Global SDR at Twilio (Segment), skyrocketed to the top in just 6 months. Learn their killer workflow for scaling prospects, unconventional omnichannel strategies, and the secret sauce for standing out in a crowded tech sales landscape.

From compelling events to AI-powered research, Jesse reveals the tools and tactics that propelled them to 164% quota attainment.

This episode is a must-listen for aspiring and seasoned SDRs alike.

Key Topics from the Episode:

---

Who is Jesse Leong (They/them)?

#1 SDR at Twillio Segment

More context about the Jesse's SDR team:

- ACV: $50k

- Industries:  B2B SaaS, retail, financial services, and healthcare

- Buyer personas: Marketing, dev, data, and product teams

- Markets: USA, and Canada

Connect with Jesse:

- On LinkedIn⁠⁠⁠: https://www.linkedin.com/in/jessemoyleong

---

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: Hacking the SDR Code

(00:59) – Rapid Immersion: Jesse's Tech Sales Experiment

(02:50) – Shadowing and Cloning: The Art of Imitation and Iteration

(04:46) – Startup vs. Market Leader: Tailoring Your Outbound Strategy

(05:28) – Challenge Accepted: Account Selection Mastery

(08:05) – Jesse's Toolkit for Identifying the "Right" Accounts

(10:03) – Data Consolidation and the "One Word Doc" Strategy

(11:13) – Scaling Outbound Without Sacrificing Quality

(12:25) – Compelling Events and the M&A Trigger

(13:23) – Segmenting for Hyper-Personalization at Scale

(15:52) – Finding the Signal in the Noise: Compiling Events, ChatGPT, and Perplexity

(21:26) – POV Outbounding and Building Confidence

(23:00) – Getting Insights From the Accounts

(25:00) – Jesse's Non-Negotiable Prospecting Stack

(27:09) – The SDR Trinity

(29:59) – Prospecting Deep Dive: Jesse's Step-by-Step Process

(32:57) – Non-Scalable Channels: High-Value and Scalable Channels

(37:57) – Jesse's Roadmap To Success in Six Months