Merritt's experience in scaling customer service operations, which happens to be one of ShopKeep's strategic differentiators, coupled with the ease with which the two were able to develop a working rapport, made the decision simple, Richelson said.

"A lot of young people feel like they have to do everything," he said. "They don't want to somehow look weak for their team. But it is absolutely vital to bring on strong people and give them equity in decision-making."

In Richelson's case, the process of being a manager to seven direct reports was distracting him from what he loved: talking to ShopKeep customers with an eye toward improving its technology. "They were frustrated with me, because I wasn't giving them what was needed," he said

Under the structure worked out by Richelson and Merritt, all of the functional aspects of the 125-person company report directly to Merritt while Richelson focuses on product vision and corporate culture. The two meet formally every Friday for at least an hour no matter where they are, although they confer frequently during the course of the week. No big decisions can be made without the other's involvement. There's also a safety value in place: both of them report to the board; if they disagree about something, that's where the issue is resolved.

"It sounded right from the very beginning," Merritt said, when I interviewed him separately about his reasons for stepping into this still rather uncommon management structure.

The two actually spent almost four months discussing all manner of strategic issues before Merritt officially joined in May in a series of courtship dinners and brainstorming sessions. "You can't just jump into something like this," Richelson said. They also debated some sample scenarios of decisions they might face day-to-day, to find out how each would approach resolutions. "We didn't just talk about abstractions, we talked about specifics," Merritt added

Obviously, the co-CEO structure won't work for every company, and this new relationship is just two months old so the jury is still out. But here are 10 questions to help assess whether or not this approach makes sense for your own organization

1. Does your company have a distinct corporate culture?
2. Does the candidate bring significant new skills or expertise to the organization?
3. How big is the overlap in skill sets between the two CEOs, perceived or real?
4. Are there well-defined processes in place for governing the relationship?
5. Is each CEO "partner" willing to collaborate on decisions?
6. Would they come to the same resolution on matters of strategic importance?
7. Do they have the same goals?
8. Does each CEO "partner" have a strong enough personality to balance that of the other "partner"?
9. If one CEO is a founder, is he or she willing to cede control of some decisions or does he or she have a tendency to micromanage?
10. Is there a board of advisors or directors that can diffuse potential conflicts?