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

ℹ️ EPISODE INFO

Released

July 12, 2023

Duration

38m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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?

1. 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?

1. 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?

1. 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?

1. 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

🎤 SPEAKERS

• Kevin Egan

  guest

• Harry Stebbings

  host

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Kevin Egan and Harry Stebbings, Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034 explores kevin Egan Reveals How to Build and Scale Elite Sales Teams 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.

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