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Troy Johnson is the SDR Enablement Program Manager at JumpCloud, where he runs the SDR New England 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 alternative

Referenced:

- Hyperbound: hyperbound.ai

- Orum: orum.com

- Troy Johnson on LinkedIn

- Gong

- ChatGPT

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When you're ready

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

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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

Grab the SDR P&L Calculator⁠⁠⁠

Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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.com

When you're ready

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

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Connect with me

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📹 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

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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

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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/

--

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

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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

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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

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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

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Ask: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Submit your questions here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ (anonymous)

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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)

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📬 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

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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

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

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When you're ready

⁠⁠⁠📫 Subscribe to the newsletter⁠⁠⁠

⁠⁠⁠👨‍🍳 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 ⁠⁠

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