Come work for MassDrive

Our Mission

Insurance shopping is confusing and tedious – but it doesn’t have to be. MassDrive wants to change the way insurance is delivered.  We're staffed by insurance pros, techies, and marketing gurus, hell-bent on making the insurance buying experience easier for everyone.

241 A St, Boston, MA 02210

Hiring in 2 Awesome Cities

5080 North 40th Street, Phoenix, AZ

Benefits of working for MassDrive

Competitive compensation and incentive plan

Health, vision and dental benefits with United Healthcare

401k Investment Plan

Career advancement opportunities

Great location near the best bars and restaurants in the city

Company Sponsored Events

Gym Membership Discount
(Boston Only)

Casual dress and work environment

Good snacks and craft beer in the fridge

What do our employees have to say about working here?
Rep, Phoenix

"The people are great, relaxed atmosphere, not micro managed, Get to save people money on insurance! What more could you want!

Oh, and Craft Beer Friday!"

Customer Advocate, Phoenix

"I love working for Massdrive because the people are wonderful and it is exciting to see our company always growing with new partnerships!"

Walter Greer
Rep, Boston

"As a licensed agent I also get to help our clients with the proper insurance coverage that they need and able to work in a fun and relaxed work environment at the same time. I recommend Massdrive to any person who wants a change in the day to day work office to apply and come and see the difference."

Open Positions

Insurance Representatives