Simply Business

Senior IT Support Engineer

Posted 6 Days Ago

Easy Apply

Boston, MA

Hybrid

Senior level

Fintech • Information Technology • Insurance • Software

We Protect The Small Businesses You Love.

The Role

The Senior IT Support Engineer will provide IT support, mentor team members, manage user technology security, resolve problems, and handle budget responsibilities.

Summary Generated by Built In

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

What the Team is Saying

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The Company

HQ: Boston, MA

1,100 Employees

Year Founded: 2005

What We Do

Simply Business is dedicated to making small business insurance simple and accessible. Our robust digital marketplace allows small business owners to find and buy the insurance they need online, matching them with coverage from multiple top insurers to offer choice, transparency, and value.

We have nearly 20 years of experience supporting small businesses, with over 1 million customers worldwide. Founded in the U.K. in 2005, Simply Business launched its U.S. operations in 2017 and today employs over 1,000 people across offices in London and Northampton in the U.K., and in Boston and Atlanta in the U.S.Simply Business is more than our name. It’s how we approach small business insurance.

Why Work With Us

Here at Simply Business we have five core values that we uphold in everything that we do: Learning, Empowerment, Authenticity, Pioneering, and Simplicity. Utilizing these values and embedding them into our culture makes SB a unique and great place to work, a place where every person is valued, a place where we get things done and have fun doing so.