Current Vacancies

IT Support Engineer

Boston, MA • Technology – IT Service & Operations • Permanent • BizOps Support
Simply Business is a digital insurance brokerage that specializes in one thing: protecting the businesses our customers are working hard to build. We’re doing this by simplifying the insurance-buying process for all small businesses, blending together a combination of technology, data, and insurance knowledge. Our proprietary technology platform allows small business owners to easily search and compare quotes from over 20 top-rated insurance providers, customize their coverage, and purchase and access their policies – all online.
Founded in the UK in 2005, Simply Business is an insurtech pioneer with nearly 20 years of experience supporting small businesses. Simply Business is passionate about building an outstanding product for our customers – one that empowers their entrepreneurial spirits.
 More importantly, we’re doing it all while taking care of our people. We’ve consistently been named a best place to work, including most recently ranking in Built In’s 2024 Best Midsized Companies to Work for in the US (Top 100), and Best Places to Work in Boston.
We want team members who have the drive to challenge boundaries. If you’re smart and passionate about delivering brilliant customer experiences, we’d love to hear from you.

Here’s what you’ll be doing:

  • Serve as an escalation point from for the Service Desk
  • Provide guidance and mentorship to the Service Desk team
  • Have the ability and willingness to help us reach the next level
  • Have the desire to automate manual processes
  • You will be hands on in supporting our user base across our Northampton office as well as remote support for our Boston (US) and London offices as well as our Polish remote colleagues.
  • Build self service solutions to help drive empowerment across the business.
  • Own and run small to medium scale projects, managing stakeholders’ expectations
  • Own problem records and collaborate with other teams in business to resolve problems as they arise
  • Develop documentation for recurring issues and feed back to Service Desk  

We’re looking for someone who is:

  • Experienced in the administration of Google Workspace
  • Experienced in the administration and maintenance of Microsoft Intune
  • Experienced deploying, supporting, and managing Apple MacBooks using Jamf MDM
  • Experienced deploying, supporting and managing Dell laptops running Windows 10.
  • Experienced of using service management and project management Tools (Fresh Service, Jira, etc).

A few more details about the role:

  • Hands on experience with identity management platforms (Jumpcloud, Okta, etc).
  • Experience supporting a complex AV environment.
  • Proven experience of developing automation across business processes. 
  • Experience scripting RubyPythonPowerShellGO.
Here are some of the great benefits and perks that come from being a Simply Business employee:
-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 5% employer match
-Commuter benefits to help cut down on parking and public transit costs
-25 days of vacation time plus 10 sick days and 10 company holidays
-A genuine investment in your learning and development-Regular team outings and volunteer opportunities 
-An awesome office space
-A hybrid working model, giving our employees great choice and flexibility to work in a way that’s best for their particular job, their teams, and their lives.
Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture. And that commitment starts with our interview process. 
Once you apply, your info will be reviewed by a team with a mix of levels and experiences. We pride ourselves on fostering a sense of community, which is only made stronger by each individual at SB, so you’ll have the opportunity to meet a variety of people throughout the process. Get excited!
Most of our first round interviews will take place over Zoom. In subsequent interviews, there may be an opportunity/expectation to meet team members in person. 
If it looks like you could be a good fit for the role, we’ll ask you to interview on Zoom first regardless – you’ll need WiFi and a laptop, or a 4G-enabled smartphone. If you don’t have access to either of these, or you need support with your application, get in touch with us at [email protected].
Please email us with any questions or if you want to pause your application for a bit – we’ll be happy to keep you updated on future opportunities like the one above. Want more info on working at Simply Business? Check out our careers page: simplybusiness.com/careers/ 

The best of Simply Business, straight to your inbox

Join 200,000+ small business owners getting helpful articles, tips, and tools — delivered direct to you.