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

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? •