Find a job you'll love At Simply Business

It's okay to love
where you work

At Simply Business, your talents are highlighted, your voice is always heard, and you’re empowered to work in a way that makes sense to you and the business. We run on a “build, measure, learn” mindset - if you have great ideas that you’re passionate about and ready to execute, we’re excited to meet you.

Join Our Team

Our Values


We’re never done learning about new possibilities and acting to explore them.


We celebrate diversity, avoid jargon and genuinely care about helping small businesses thrive.


We simplify complex solutions to save our customers time and effort


We believe in our people and the positive impact they can have, so we enable everyone to stretch themselves.


We're obsessed with finding new ways to create even better experiences.

Our Culture

“Exciting” might not be the first word that comes to mind when you think insurance. But we’re a little different here. From our flexible working hours to fun outings with the team, Simply Business is designed to celebrate, encourage, and support the people who make us who we are. It’s our ultimate goal to create the kind of workplace where you don’t dread getting up on Monday morning.

Right now we’re at the start of an incredible journey. If you’re smart, passionate about delivering brilliant customer experiences, and enjoy solving complex problems, then you’ll fit right in here with us.

A group of Simply Business employees at a meeting
A group of Simply Business employees playing with a dog

What are the benefits?

Working in our Boston Office, you will have the chance to shape a business from the very beginning, and an opportunity to develop and learn new skills across various technology and business areas as you desire. Plus there’s all the serious (but important) stuff we call "core benefits."

The Core Stuff

Some of these will kick in once you’re confirmed in post, but here’s the summary:

  • A salary that reflects your experience, our pay policy and the market we’re in from your first day
  • Group plan for medical, dental, and prescription drug coverage
  • Short term disability, long term disability and life insurance coverage
  • Participation in the Company’s bonus program
  • Participation in 401(k) plan with a 3% employer match
  • Commuter benefits to help cut down on commuting costs
  • 25 days of vacation time plus 10 company holidays

The Fun Stuff

But there’s so much more to Simply Business than insurance. We also commit to flexible working options, smart working (our offices are outfitted for you to work when and how you choose) and we have a handy online form to put in any training or conference requests.

Best of all, though, are the groups, clubs, and adventures that come with the Simply Business territory. We trek the Sahara for charity, take you on weekends away, throw epic summer parties, meet up for book groups, public speaking coaching and lots, lots more.

It’s a big claim but we believe the Simply Business culture is truly unique. You sort of have to come and spend time with us to appreciate it. So get that application in and we’ll take it from there.

    How We Interview

    We get it: Interviews can be nerve-wracking. That’s why we try to make the process a little easier by preparing you as much as possible to meet our team. We’ll let you know who you’re meeting, what team you’ll be joining, and how your role will help our company grow.

    Simply Business job interview

    Chat with your hiring manager

    You’ll have a quick video or phone chat with your hiring manager, so we can get a better feel for who you are.

    Come into the office

    During your in-person interview, you’ll chat with multiple team members from across the organization. Expect to spend about three hours in our office.

    How to prepare

    We recommend that people bring their resumes. If your role requires a presentation, we’ll let you know ahead of time.

    How to prepare for tech jobs

    Before your in-person interview, we’ll provide you with a programming assessment so we can better understand your skills. Expect to spend about three hours in our office.