Who needs a solo act when you can have a dynamic duo? In Part Two of this series, Mary Shea, General Manager of Hire Quotient and former co-CEO of Mediafly, takes us inside the world of co-CEOship—a growing leadership trend that’s part genius, part juggling act.

Mary unpacks what makes it work: trust, complementary skills, and a shared vision. But she’s also refreshingly candid about the pitfalls—slower decision-making, the need for a strong board, and why even the best co-leaders need a “business couples counselor.” If you’re rethinking leadership structures, this one’s for you.

AI’s Impact on Sales Teams

“AI is paving the way for smaller, more agile sales teams, moving away from the traditional 80/20 rule toward a future where 80% of the team delivers 100% of the revenue.”

The Rise of the Consultant Seller

“AI acts as a coach on the salesperson’s shoulder, helping them become more advisory-oriented, and enabling deeper impact in customer interactions.”

Why Two CEOs?

“In today’s complex world, no single leader can address everything, from geopolitical challenges to the rapid pace of AI innovation. The co-CEO model allows for a divide-and-conquer approach.”

Challenges of Co-Leadership

“Decision-making can be slower, and sometimes we wish we could just do things our way. But alignment is key, and when it works, it’s incredibly impactful.”

Who’s the Umpire?

“Our ‘umpire’ is our investor and board. If we truly can’t resolve a disagreement, we rely on their input as the ultimate decision-maker.”

The Professional Marriage

“Co-CEOship is like a professional marriage—it requires resilience, commitment, and sometimes even a ‘marriage counselor’ in the form of an executive coach to navigate tough patches.”

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