20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Dan Fougere is one of the most successful sales leaders of the last decade. Most recently, Dan was Chief Revenue Officer for Datadog, growing revenues from $60 million to $1BN ARR. Before Datadog, Dan was Head of Global Sales at Medallia where he created the Mediallia sales playbook. In addition, Dan is also a minority owner of the New York Yankees.

In Today’s Episode with Dan Fougere:

1. Lessons Scaling Sales to $1BN in ARR at Datadog:

• What did Datadog not do that Dan wishes they had of done?

• What did they not do that Dan wishes they had done?

• What does Dan know about scaling sales to $1BN in ARR that he wishes he had known at the beginning?

• What stage of the scaling process was hardest? Why?

2. How to Hire the Best Sales Team:

• What are the top signals of the best sales candidates?

• How does Dan structure the interview process for new candidates?

• How does Dan use tasks and take-home assignments to test candidates?

• What does Dan think of hiring panels?

• What are the biggest hiring mistakes Dan has made? What did he learn?

3. Discounting, Logos and Deal Reviews:

• Is discounting always wrong? How should sales leaders use it?

• How important is the quality of logo in the early days vs revenue in the door?

• What is the right way to structure deal reviews? What makes good vs great?

• Is outbound dead in 2024? Advice to founders on outbound?