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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 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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Connect with me

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 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)

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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/

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When you're ready

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

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Connect with me

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 Connect on LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 Subscribe on YouTube ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 Connect on X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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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

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Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

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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.

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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

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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

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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

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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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠

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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