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20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

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Jul 12, 2023

Kevin Egan, Global Head of Enterprise Sales at Atlassian, shares his wealth of experience from top tech companies like Slack and Dropbox. He discusses the traits that make an exceptional sales leader and reveals insights on crafting an effective sales playbook. Kevin explores the transition from product-led growth to enterprise sales and warns of common pitfalls. He emphasizes the importance of hiring adaptable sales talent and creating a collaborative leadership environment, all while leveraging technology and transparency for sales success.

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ADVICE

Compensation and Long-Term Vision

Focus on long-term vision and company culture when discussing compensation.
Ensure fairness, but prioritize candidates excited about the journey.

ADVICE

Building Trust Through Evolving Management

Transition from directive management to a partnership as hires develop.
Clearly defined expectations build early trust and empower growth.

ADVICE

Maintaining Hierarchy and Trust

Establish hierarchy by demonstrating a broader scope of responsibility.
Provide direct feedback when necessary, focusing on expectations.

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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.

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?