If you didn’t make it to our BostonFest blowout Thursday night, first of all, shame on you. Second of all, we’re still going to fill you in on the winners of our Coolest Companies Competition for 2016 because we won’t leave you hanging like that.

This year, the competition was stiff. We had a motley crew of finalists – from high-tech companies in the Seaport to boozy businesses in the South End – vying to be crowned one of the 10 Coolest Companies in Boston. But clearly not everyone could make the cut.

Below, we give you the 10 winners of BostInno’s Coolest Companies 2016, along with a few reasons as to why they’re so damn awesome. They’re listed in alphabetical order. Enjoy.


  • They’re doing their part to increase diversity in tech by publishing its diversity data.
  • Cupcakes are considered “a guaranteed benefit in every employee’s offer letter,” according to their marketing communications manager Michelle Berman.
  • They hold an eclectic selection of activities – from ski trips to cooking classes – for employees throughout the year.


  • This year, they secured $35M in Series B funding and added Brad Feld, VC extraordinaire, to its board.
  • They host family lunches where co-workers and their loved ones can have serious bonding time with each other.
  • They have rad parties, the last of which included a moon bounce.


  • They just had major news, being part of a $1.8 billion merger with Citrix.
  • Guess who has basketball court in their office? Swoosh.
  • They kick off the year in January with company-wide trips to exotic destinations. Cancun, anyone?

Night Shift Brewing

  • Beer.
  • Employees receive perks, like a monthly Taproom and beer stipend, unlimited vacation time and a free membership to their Barrel Society.
  • In the past, company outings have included canoe trips, games of bowling and a bar crawl in Davis Square.


  • CEO Bettina Hein previously shared with us that her employees hang out with each other all the time outside of work.
  • They host weekly in-office picnics where employees aren’t allowed to eat at their desks in order to have real conversations with their co-workers.
  • Who said tech companies have to stick to the Seaport? Their nice digs are in the North End. Here’s the office envy we did back in March.


  • They’re in the podcast business and it syndicates good listens like This American Life and The Moth.
  • Allston is now home to PRX’s recently opened “podcast garage” where people can rent space and equipment to record a podcast for a nominal fee.
  • Pairing up with Aeronaut Brewery, they’re holding happy hours at their new podcast studio space.

Rapid7 (Readers’ Choice)

  • They have a Moose Manifesto (not making this up). And I quote, “At Rapid7, we refer to ourselves as ‘Moose.’ Since the plural of moose is moose, we consider ourselves ‘One Moose.’”
  • They’re so cool they downplayed their startup perks – like catered lunches, unlimited vacation time and cornhole competitions – in favor of the team-driven culture they’ve created.

Spartan Race

  • They work out. A lot. They’ll just break into burpees during lunch, competing for sushi.
  • Their races have been televised on NBC.
  • They have an “Everest Challenge”, which entails climbing a whole lot of stairs to get to the office.


  • They’re big on board games and employees can create clubs to enjoy their hobbies with like-minded coworkers.
  • Given the nature of their work, employees frequent their fair share of food shows.
  • This winter, they closed $30 million in Series B.

Wayfair (Readers’ Choice)

  • They have all the startup perks covered: snacks walls, employee fitness classes, boozy happy hours and tables – of both the ping pong and foosball variety.
  • Their office is impeccably decorated, as one would expect.
  • Oh, and their space is a sprawling 120,000 square-feet in Back Bay.

This article has been updated. Image via Pretty Instant.