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Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce. -------------------------------------------- Timestamps: 0:00 Who is Kevin Egan 1:13 Lessons from Salesforce, Dropbox & Slack 4:35 The Sales Playbook 7:30 When to Movie Into Enterprise 13:35 How to Identify & Hire Talent 21:27 How to Structure Comp Packages 26:00 How to Give Feedback 31:25 How to Do Discounting 35:30 Quick-Fire Round -------------------------------------------- In Todays Episode With Kevin Egan We Discuss: 1. The Makings of a Truly Great Enterprise Sales Leader: How did Kevin first make his way into the world of enterprise sales? What does Kevin know now that he wishes he had known when he entered sales? What advice would Kevin give to a new sales leader today starting a new role? 2. The Sales Playbook: How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook When is the right time to hire your first salespeople? Should they be senior or junior first? What are the different types of reps to hire in the early days? Should you hire two at a time? 3. PLG vs Enterprise: Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time? How does one know when they are ready to scale from PLG into enterprise? What are the signs? What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales? What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise? 4. Hiring the Sales Team: What non-obvious characteristics and attitudes should we look for in sales reps? How does Kevin structure the hiring process for all new additions to sales and revenue teams? What makes good PLG sales leaders? How are they different from enterprise sales leaders? What questions and case studies are most revealing for you in identifying them? What have been some of Kevin's biggest lessons on comp structure for these early rep hires? 5. Making the Machine Work: How does Kevin build trust with his early sales rep hires? What works? What does not? How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy? How does Kevin manage when a quarter is missed? What is the right approach? How does Kevin approach post-mortems and deal reviews? How often? What do the best entail? ------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact -------------------------------------------- #KevinEgan #Atlassian #HarryStebbings

Kevin EganguestHarry Stebbingshost
Jul 11, 202338mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Kevin Egan Reveals How to Build and Scale Elite Sales Teams

  1. Kevin Egan, veteran sales leader at Salesforce, Dropbox, Slack, and Atlassian, breaks down how to build, hire, and manage high-performing sales organizations from early-stage startup to scaled enterprise. He reframes ‘sales playbooks’ as dynamic sales motions rooted in deep understanding of customer problems and product value, not scripted steps. Egan explains how to transition from PLG to enterprise, including technical, organizational, and sales-structure changes, plus how to measure rep effectiveness and run rigorous hiring and deal-review processes. He also dives into comp plans, discounting, forecasting, and feedback, emphasizing fairness, long-term alignment, and direct, well-calibrated communication as foundations of trust and performance.

IDEAS WORTH REMEMBERING

5 ideas

Treat ‘sales playbooks’ as evolving sales motions grounded in customer problems.

Rather than rigid step-by-step scripts, top sellers start from who the buyer is, what problems they face, and how the product uniquely solves those problems, then codify those motions into repeatable patterns.

Sequence PLG and enterprise; don’t assume you can fully do both at once.

Slack nailed end-user love and virality first, then invested heavily for years in enterprise-grade security, compliance, and process; enterprise is not a feature checklist but an ongoing, ‘no finish line’ commitment.

Early-stage sales hires must have broad ‘intellectual range,’ not just big logos.

In young companies, the first sales leaders need to write messaging, close deals, gather product feedback, and build process; someone from a marquee brand without this range will often fail despite their résumé.

Use structured, multi-step hiring with a live mock sales scenario.

Candidates should pass through several interviews and a ‘stand and deliver’ mock meeting presenting to a fictitious or real product scenario; consistency across interviews and their ability to command the room are key signals.

Design comp plans to be fair and use them to test for long-term alignment.

Market-aligned compensation is table stakes, but Egan watches whether candidates focus only on OTE and short-term payout versus the broader growth journey and career upside of joining a ‘rocket ship’.

WORDS WORTH SAVING

5 quotes

I don't typically use the word playbook… I prefer the term sales motions.

— Kevin Egan

It is naive to think it's just a few features… enterprise is a lifelong pursuit.

— Kevin Egan

Early days are really about who is creating the best connection between my developing product and my potential customer.

— Kevin Egan

When I hear, ‘It slipped to next quarter,’ what I'm looking for is, did you commit it to this quarter?

— Kevin Egan

Good discounting should originate from the office of the CFO.

— Kevin Egan

Differences between product-led growth (PLG) and enterprise sales motionsDesigning and codifying effective sales motions (vs static playbooks)Hiring, evaluating, and compensating early sales reps and leadersStructuring sales orgs and transitioning from PLG to enterpriseEnterprise readiness: security, compliance, reliability, and data requirementsRunning deal reviews, forecasting, discounting, and managing procurementLeadership, hierarchy, trust-building, and delivering direct feedback

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