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Find a job you'll love at Simply Business


Insuring small businesses. Enabling big dreams.

That’s our mission here at Simply Business.

But it’s not just for our customers. It’s for our people. Our communities. For you. Here’s how we achieve that mission:

We embrace your individuality

We see each person as an authentic individual with their own big dreams. That’s why we support our employees in recognizing those big dreams, all while supporting their wellbeing and growth. After all, no two people are alike - and at Simply Business, we treat every employee as the unique individual they are.

We’re innovative

We foster a place for people to be curious, experience new things, and bring unique ideas to the table. We listen to our customers and innovate to launch new products and services that meet their needs. We may be backed by a giant, but we’re always finding ways to be agile.

We trust who we hire

Finally, we empower SBers with choice and flexibility to make the right decisions based on the needs of our roles. Feedback, coaching, and learning keeps us honest and further builds trust.

Join Our Team


Our values

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We’re always learning, developing and improving, and helping others do the same.

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We respect the unique skills and perspective that everyone has.

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If we can make it simpler, we do, and if we can’t then we explain it so everyone can understand.

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We’re trusted to get the right stuff done in the way that suits us best.

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We lead with purpose and make things happen.

Our Better Normal

More and more, people are talking about going back to the workplace and the new normal. At Simply Business, we’re thinking of it as a Better Normal. That means offering our SBers more choice and greater flexibility to work in a way that’s best for their particular job, their teams, and their lives.

We’re shifting to a hybrid working model, so we’ll have employees working virtually and in the office at any given time.

We’re also aware there are times when working together in person is the best way to get things done. We expect our SBers to connect in their hubs (that’s what we call our offices) most likely once every few weeks. That said, there’s no one-size-fits-all solution, so we expect all SBers and their teams will find the operating rhythm that works best for them.

If you’re wondering what it might be like for you at Simply Business, our Talent Acquisition team is happy to answer any questions. In fact, for them, it’s perfectly normal.


What are the benefits?

Working in one of our hubs, you will have the chance to shape a business from the very beginning, as well as enjoy the opportunity to develop and learn new skills across various technologies and teams. Plus there’s all the serious (but important) stuff we call "core benefits."

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The Core Stuff

  • A salary that reflects your experience, our pay policy and the market we’re in from your first day
  • Group plan for medical, dental, vision, 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
  • 25 days of vacation time plus 10 company holidays and 10 sick days
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The fun stuff

But there’s so much more to Simply Business than insurance. We also commit to flexible working options, remote working opportunities, access to great office space, and plenty available training to help you develop in your career.

Best of all, though, we have a greatly connected culture, even when we’re in a remote environment with groups, clubs, trivia nights, guest speakers, charity drives, and more. We trek to Costa Rica for charity, take you on a company trip away, throw epic parties, meet up for book groups, coaching and lots, lots more.

It’s a big claim but we believe the Simply Business culture is truly unique and something you have to experience for yourself! 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.

careers interview

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Chat with your recruiter and hiring manager

First up, you’ll chat with one of our recruiters so we can get a better feel for who you are outside of just your resume. Next thing, you’ll have a quick Zoom chat with the hiring manager to learn more about the ins and outs of the role and their team. (Some roles will skip this step).

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Virtual "on-site" interview

The majority of our interviews are taking place entirely over Zoom these days. You’ll chat with multiple team members across the organization. Expect to spend about two to three hours on Zoom with our team. Please note: our TA team will let you know if an onsite interview might be required for your role.

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How to prepare

We recommend having your resume on hand and be prepared to discuss what makes you great for the role and what sets you apart! If your role requires a presentation, we’ll let you know ahead of time.

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How to prepare for tech jobs

Before your virtual “on site” interview, we’ll provide you with a programming assessment so we can better understand your skills. Expect to spend about three hours on Zoom with some of our team.


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Simply Business1 Beacon Street, 15th FloorBoston, MA02108


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*Harborway Insurance policies are underwritten by Spinnaker Insurance Company and reinsured by Munich Re, an A+ (Superior) rated insurance carrier by AM Best. Harborway Insurance is a brand name of Harborway Insurance Agency, LLC, a licensed insurance producer in all 50 states and the District of Columbia. California license #6004217.

© Copyright 2022 Simply Business. All Rights Reserved. Simply Business, LLC is a licensed insurance producer in all U.S. States and the District of Columbia. Simply Business has its registered office at Simply Business, 1 Beacon Street, 15th Floor, Boston, MA, 02108. In the state of California, we operate under the name Simply Business Insurance Agency, Inc., License #0M20593. In the state of New York we operate under the name Simply Business Insurance Agency. In the state of Texas we operate under the name, U.S. Simply Business, Inc. For more information, please refer to our Privacy Policy and Terms & Conditions.