Here’s When It Actually Makes Sense to Have Co-CEOs

Salesforce shouldn’t have had two CEOs, but there are moments in a company’s life when it makes sense to have dual leaders

Joe Procopio
Published in
7 min readMar 9, 2020


Former Salesforce co-CEO Keith Block.
Former Salesforce co-CEO Keith Block. Photo: Joanne Rathe/The Boston Globe/Getty Images

To paraphrase an old saying: When you have two CEOs, you have no CEO.

I think we just saw that adage play out last month at Salesforce, when Keith Block, who was elevated to co-CEO just 18 months ago, suddenly stepped down, leaving founder Marc Benioff as the sole Salesforce CEO once again.

Block will remain on as an adviser for Salesforce, and his resignation was announced in the midst of celebrating a strong quarter. But regardless of the positive spin, it appears that having two leaders just didn’t work out for Salesforce.

News like this tends to highlight the drawbacks of a co-CEO structure: Two leaders means a series of split decisions and bickering. Two leaders means mixed messages and incongruent priorities. Two leaders means everyone has two bosses.

But it doesn’t have to be that way. A company having two CEOs can work. In fact, there is a time in a company’s life cycle when it works extremely well; in the growth stage of a startup, having two leaders is almost necessary. It’s a period rife with some undeniable problems that always bubble up at the top level of startup leadership.

There’s just too much for one person to do

Raise your hand if you’re a CEO with too much free time.

I’ve been in the startup world for over 20 years, and the amount of work I’ve seen loaded onto a CEO’s shoulders (including my own) has increased steadily throughout that time. I understand the pressure that a CEO feels to work themselves to the bone and give the so-called 110%. But the math on giving 110% usually breaks down to giving 10% across 11 different priorities.

Once a company stabilizes and becomes something that no longer resembles a startup, the CEO job takes on a new meaning.

At the beginning of a startup’s life, when the team is small and everyone is wearing multiple hats, it absolutely makes sense to have…



Joe Procopio
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I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at