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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

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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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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠🐦 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

⁠⁠⁠⁠📫 Subscribe to the Outbound Kitchen newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠📌 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