In SaaS, The CEO Never Gets to Step Away From Sales

Dear SaaStr: When Should The CEO Step Away From Sales?

Never. It’s just, as you scale, what you do in the sales process as CEO evolves and changes.

I remember when we closed Groupon as one of our Ten (or so) Largest customers, back in the day. They’d brought us on shortly after they’d deployed Salesforce all across the company. My guess is they paid Salesforce $20m a year back then. We flew out for a Big Hands On, in the bitter middle of a Chicago winter.

My VP of Customer Success, VP of Product, and I were in one small conference room working with the Sales Operations team. Talking about how to deploy faster, better, bigger.

Across the floor, with the then 25-year-old CEO Andrew Mason … was Marc Benioff and his team. He’d flown out to Chicago in the dead of winter as well, probably all the way from Kona, who knows. He knew he had to be there, too.

Anyhow, he was still selling, the CEO of Salesforce. Salesforce was probably worth $10 billion then. It’s worth $220 billion today. And he’s still selling.

That’s your answer.

Are you still doing 10+ customer meetings, calls and Zooms a week after you hire your first (or second) VP of Sales? If not, you’ve stepped out of sales too much.

And if sales doesn’t go up, at least a smidge after you hire a VP of Sales — then you stepped out of sales, even just a smidge bit, too early. Get back in. Join deal reviews. Listen to 20 Gong calls. Understand why you lost every deal you lost this month.

One of the top mistakes I see from founders once they hire their first VP of Sales is stepping away from sales.

It doesn’t work that way. Yes, a great VP of Sales will take over a lot of the sales processes from you, and sales recruiting. But you don’t get to stop doing sales. Instead, you as CEO repurpose that time to support deals and drop into deals. Not create them and close them. But that time? You never get that time back. It just changes.