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The Senior IT Support Engineer will provide IT support, mentor team members, manage user technology security, resolve problems, and handle budget responsibilities.
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 2025 Best 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:
You’ll be part of an IT Support team that provides simple, intuitive, and hassle-free IT support to your colleagues. You’ll help make sure every Simply Business employee has reliable IT systems – and quite literally keep our engine room humming.
You'll be reporting into Stuart (our BizOps Support Lead), who is based in the UK. Stuart prides himself on his carefully selected team, who provide support for all things IT for the global business. The team has regular team building days to keep you engaged, inspired, and enthusiastic about your role.
Heres what you'll be doing:
- serving as an intermediary escalation point between our 2nd and 3rd line teams
- providing guidance and mentoring to the 1st and 2nd line teams
- assisting the Support Lead in supervising the team
- building self service solutions to help drive empowerment across the business
- working with the security team to make sure user technology is in line with the company's security standards and best practices
- owning problem records and collaborating with other teams to resolve problems as they arise
- taking budgetary responsibility for a small number of services
- working with key business stakeholders to understand requirements and implement processes or technical solutions
We're looking for someone who is:
- experienced in the administration of Google Workspace
- experienced in network administration
- experienced in the administration and maintenance of Microsoft Intune
- experienced deploying, supporting, and managing Apple MacBooks using Jamf MDM
- experienced deploying, supporting, and managing laptops running Windows 10
- experienced using service management and project management tools (such as Fresh Service and Jira)
- passionate about attention to detail and doing things the right way
- experienced in medium to large scale projects
- experienced in supporting and setting up Meeting Room AV equipment
- experienced in managing vendor relationships
A few more details about the role:
- hands-on experience with Jumpcloud/OneLogin and Okta identity management (LAAS - LDAP as a service) is desirable
- experience scripting with Bash, Python, and PowerShell is desirable
- experience developing automations is desirable
- experience in Agile iterative and incremental work practices for project delivery
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/
Top Skills
Bash
Fresh Service
Google Workspace
Jamf Mdm
JIRA
Microsoft Intune
Powershell
Python
Windows 10
Simply Business Boston, Massachusetts, USA Office
We are located in downtown Boston, accessible to every line on the T and surrounded by a lot of history and a lot of great places to grab lunch.
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