Senior IT Support Engineer

Simply Business is a digital insurance brokerage that specializes in 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.

As our Senior IT Engineer, you’ll be the vital link between our 2nd and 3rd line teams, moving beyond standard fixes to build a more resilient, automated environment. You’ll act as a mentor and builder, supervising team growth, taking full ownership of problem records, and developing self‑service tools that empower our people to work smarter.

• Act as the key escalation point for complex technical issues, bridging the gap between 2nd and 3rd line support teams.
• Mentor and guide the 1st and 2nd line teams, sharing your expertise to help them level up their skills.
• Hunt down root causes by owning problem records and implementing permanent, refreshing solutions.
• Manage our device fleet, overseeing Mac Books via Jamf alongside Windows 10 and Chromebooks.
• Administer core environments including Google Workspace and Microsoft Intune to keep our tech stack seamless.
• Champion self‑service by building tools and documentation that remove complexity for our users.

• An expert in modern device management, specifically with Google Workspace, Microsoft Intune, and Jamf (Jamf 300 preferred).
• A skilled automation enthusiast who uses Bash, Python, or Power Shell to replace manual tasks with smart, efficient scripts.
• Experienced in Identity Management, comfortable working primarily with Okta (bonus points for Jump Cloud or One Login).
• A project‑oriented professional used to managing medium to large‑scale projects within Jira.
• Knowledgeable in AV Support, ensuring our Zoom and Google Meet environments remain high‑performing.
• Obsessed with detail and passionate about “doing things the right way” to keep our tech safe and compliant.

• 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. We encourage people of all different backgrounds and identities to apply.