ACQ2: Mastering Enterprise Software Sales with Bill McDermott

We sit down with ServiceNow CEO Bill McDermott for a masterclass in the art of enterprise sales — a topic where Bill ranks as one of the all-time greats by any measure. Bill started his career as a bag-carrying salesman at Xerox in New York City (alongside Howard Schultz!) back in 1983, and rose to become the company’s youngest corporate officer at age 36 before going on to become CEO of global software giant SAP. Since joining ServiceNow in 2020 Bill has grown the company from $3.5 billion in revenue over $10 billion today, and a nearly $200B market cap — which makes it one of the largest enterprise software companies in the world. Whether your job directly involves selling or not (and if you’re a founder, make no mistake — selling is the MOST important part of your job) there’s something here to be learned for everyone. Break out your notebooks and enjoy!

Links:

- ServiceNow: https://www.servicenow.com
- The SPIN selling method: https://www.highspot.com/blog/spin-selling/
- Bill’s fantastic interview with Ben Thompson on Stratechery: https://stratechery.com/2025/an-interview-with-servicenow-ceo-bill-mcdermott-about-enterprise-ai-agents/