When I wanted to contact Dharmesh Shah, CTO of Hubspot yesterday, I couldn’t rely on his normal email. No, for that one day the way to reach Shah was dharmesh@kayak.com. That’s right. As you may have seen on Twitter, Shah and Kayak CTO Paul English swapped roles for the day, each reporting to the other’s desk to work with the other’s team at the company the other one founded.


First, I’m sure it was a fun change of pace for everyone involved. But beyond that, it was a chance to bring an outside perspective into both companies. As Shah aptly noted via his Kayak email address:

The coolest part of the thing (for me) was getting to spend time talking to really smart people that are in a different industry.  And, I get to ask really simple questions.

Don’t underestimate the value of simple questions. Companies pay big bucks to bring in young grads as consultants in part for this purpose: to ask the fairly obvious questions that those who’ve been in the trenches too long no longer think to ask.

And English, who came up with the idea for the switch, is big on this premise in general. That’s why he doesn’t hire developers with experience in the travel industry. He sees every hire as the chance to get a new set of eyes.

I asked Shah what his day consisted of. He wrote:

I spent the day at Kayak.  I sat at Paul’s desk here.  Had a bunch of meetings setup with various folks on the Kayak team.  The rest of the time, I’ve been reading/responding to Kayak email and letting people walk up and chat.

Of course, you can’t just step into a CTO role for a day and act as you normally would. But any loss of productivity has to be more than made up for by the boost to morale and the benefit of getting an outside view on some problems. Although Shah did note that he enjoyed seeing the ways the two companies were the same as much as seeing how they were different.

This kind of stuff is part of why everyone in Boston knows and likes these companies, and why people want to work at Hubspot and Kayak. It shows that they’re fun and original, and that their founders are willing to step back from the daily grind of running their business to interact with the broader community. Put simply, Boston needs more of this.

If you don’t believe me and think I’m making too much of the whole thing, take a look at the tweets:

Shah’s email, sent at 5:08pm last night, ended abruptly: “I’m sneaking this email in between meetings.  Need to get back to work  :)”