Revenue Builders Podcast: “All You Need To Know About Good Leadership” with Jeremy Duggan

Podcast: Revenue Builders
Hosts: John McMahon (“Johnny Mac”) & John Kaplan (“Cap”)
Guest: Jeremy Duggan
Air Date: May 26, 2022

Episode Overview

In this episode of Revenue Builders, John Kaplan and John McMahon sit down with renowned sales leader Jeremy Duggan, whose track record includes transforming companies like AppDynamics and Multiverse into billion-dollar organizations. The conversation centers on actionable leadership principles and building high-performance sales teams—anchored in Jeremy’s “Three Rs” framework: Recruiting, Retention, and Revenue. Duggan offers concrete advice for sales leaders at every level, blending data-driven insights, leadership authenticity, and lessons from his own journey.

Key Discussion Points & Insights

1. The "Three Rs" Framework for Scaling Companies

Timestamps: [04:03]–[07:12]

• Recruiting, Retention, Revenue:

  • Jeremy attributes scale and success to excelling at all three.
  • "If you recruit great people and then you can retain and inspire those great people and then you have a fact-based methodology around how to drive results... then you've got a fantastic shot of building a really incredible company." (Jeremy, [06:23])

• Data Over Intuition:

  • Duggan's approach was shaped at PTC, seeking fact-based (not just opinion-based) patterns of excellence.
  • "I never wanted to go to people and say, 'here’s what I think is the right thing to do, let's just do it.' ... You have to win with data and with facts and with history and with logic." (Jeremy, [05:15])

2. Recruiting: What Makes an A Player?

Timestamps: [07:13]–[13:05]

• Defining the A Player:

  • "Are they smart, intelligent, do they have character—resilience, determination, loyalty, and honor? Are they coachable? Do they want to learn? Experience is really nice to have, to be honest with you." (Jeremy, [09:15])

• Talent Magnetism:

  • "People join people."
  • To win great talent, you must offer inspiration, growth, and real development—not just compensation. A-players expect to join other A-players and be genuinely inspired by leadership and team.

• Culture Risk:

  • Hiring below the standard impacts team morale; one low-bar hire can drive A-players out.
  • "Within three months they were struggling and the A players were coming into our office going, 'What are we... we don't want to be great anymore. What's going on?'" (Jeremy, [14:15])

3. Retention: Inspire and Develop

Timestamps: [13:25]–[17:47]

• Development & Inspiration:

  • "The retention piece is about inspiring development in people. But you’ve got to take strategy and have everybody executing it, right? All the time." (Jeremy, [14:49])
  • Story of a Multiverse interview: Jeremy emphasizes excellence across all interactions. “Imagine if we did 800,000 brilliant calls, how much further ahead the company will be.” ([15:24])

• Culture of Excellence:

  • Excellence must be consistently modeled, coached, and expected at every level.

4. Leading Through Data—The Power of the Playbook

Timestamps: [18:27]–[21:34]

• Battle for Buy-in:

  • "What I say to people here is, when I talk to you about leadership in the three R's or the leading indicators in sales, what I'm actually doing is I'm handing you the winning lottery numbers." ([18:57])
  • The combination of track record, logic, and proven process accelerates trust-building with new teams.

• Execution & Inspection:

  • "5% is the idea, 95% is the execution."
  • Inspections (forecast reviews, pipeline, etc.) should be used for development—not micromanagement. “If your true purpose for inspection is to help someone to develop... nobody really cares about inspection anymore because it's a mechanism for improvement.” ([22:07])

5. Personal Leadership Journey & Self-Awareness

Timestamps: [23:25]–[28:29]

• Overcoming Setbacks:

  • Duggan was initially told he lacked what it takes for management, but used it as a catalyst:
    • "He was right… I was a great sales guy, but I didn’t really know why… So that really started me down the line of trying to educate myself on what great things look like." ([24:55])
  • Practiced continuous self-coaching after each major stint—taking sabbaticals to reflect and upgrade.

• Candid Feedback:

  • On transparency:
    • John McMahon: "People get a sense from you that they get 99% of the information, but not the 1%." ([29:12])
    • Duggan now strives for "full transparency for good or for bad" ([30:02]), realizing that leaders must proactively invite help and not “fail alone.”

6. Authentic Leadership & The Danger of Imitation

Timestamps: [32:29]–[36:15]

• Being Yourself:

  • PTC's explosive growth spawned leaders imitating John McMahon and Dick Harrison—but without the necessary charm, devolving into unintentional bullying.
  • "You’re not going to do it the way Kaplan does it… You have to find your way… But fundamentally, you’ve got credibility and you care about people." ([35:15])

• Self & Social Awareness:

  • McMahon to his teams: "What's the book on you?"—testing self-perception versus external perception.

7. Leading with Data—Science & Art

Timestamps: [38:12]–[45:23]

• Data is Essential—But Simplicity Matters:

  • "How do you develop somebody when you don’t have data on them? …You’re looking around for a lightbulb in the dark. That’s what you’re doing without data." ([39:24])
  • Effective leaders demand clear, digestible data—not overwhelming spreadsheets.
  • The rapport with operations/finance is crucial: leaders must define what data they need to drive action.

• Balancing Data and Individuality:

  • McMahon adds: intimacy with your people matters—leaders can't "cookie-cutter" the process—artists may need different management, but data can still empower them.
  • "If you have data and that drives success, you get an artist… that data can make the artist better." (Jeremy, [44:00])

8. The Value Pyramid: Executive Engagement

Timestamps: [49:02]–[53:27]

• From Product Pitch to Executive Relevance:
  • Duggan’s Value Pyramid: Anchor every sales interaction in real research—understand the company’s annual report, CEO letter, priorities, strategy, and challenges.
  • "Every salesperson comes in and they effectively show their brochure … come and do your research, man." (Jeremy, [50:18])
  • By aligning with the customer’s value creation objectives, you become a peer—not just a vendor.
  • Impact: Jeremy's meeting conversion rate jumped from 25% to 75%. ([53:10])

Notable Quotes, Moments & Lessons

• On A-Player Recruiting:
  "Most people say 'experience,' but not every CMO is going to be right for you... Are they smart, do they have character, are they coachable—experience is nice to have." (Jeremy Duggan, [09:00])

• On Inspiring Teams:
  "Great people want to be inspired and developed. Their whole outlook on life, capability, opportunity—is different when they finish that journey." (Jeremy, [10:36])

• On Inspection & Culture:
  "If you figure out a way to make them all great, everyone above you can love you anyway." (Jeremy, [23:04])

• On Leadership Setbacks:
  "I was a great sales guy, but I didn't really know why … [the feedback] really started me down the line of trying to educate myself on what great things look like." (Jeremy, [25:05])

• On Authentic Leadership:
  "You’ve got to find your way, right, of leading … you don’t have to be somebody that you look up to." (Jeremy, [35:12])

• On Data and Simplicity:
  "Some people think the more data you have, it shows you’re in control … but there’s a genius in simplicity." (Jeremy, [41:20])

• On the Value Pyramid:
  “You stop being the 99% of salespeople who show up and try to flog something … you're the guy that's gone in and you've taken the time to research and respected their time.” (Jeremy, [52:45])

• On Continuous Improvement:
  "I always take a little gap at the end … After BladeLogic and BMC, I took nine months out and I studied what I did well and tried to add to it, and I studied what I didn't and tried to replace it…" (Jeremy, [27:15])

Additional Highlights & Fun Rapid Fire (Lighthearted Wrap-Up)

• Ideal day off: Watching Chicago PD
• Favorite meal: Burger and chips
• Favorite movie: "Annie" or "The Sound of Music" (not the Godfather) ([57:53])
• Charity: Save The Children UK—Jeremy and his son raised $150,000 climbing Mt. Kilimanjaro

Suggested Listening by Segment

• [04:03] The Three Rs explained
• [09:00] Defining A-players
• [14:49] Retention and culture
• [24:46] Jeremy’s first leadership rejection and mindset
• [29:12] On transparency & leadership feedback
• [38:12] Data-driven leadership
• [49:57] The Value Pyramid and executive selling

Summary for Listeners

This episode is packed with hard-earned wisdom on sales leadership—from assembling and keeping elite teams to balancing artful people management with science and process. Jeremy Duggan’s practical frameworks, humility, and humor make this a can't-miss masterclass for ambitious sales leaders.

“If you take care of recruiting, retention, and revenue with fact-based processes and care for your team, you’re not guaranteed success—but you’re giving yourself the best possible shot.” — Jeremy Duggan ([06:18])