Senior IT Support Engineer

Who Are We?

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.

Job CategoryTechnologyPosition TypePermanentCompensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range$77,600.00 - $128,000.00Target Openings1What Is the Opportunity?Here's what you'll be doing:
We’re on a mission to simplify insurance for small businesses by blending data, technology, and genuine expertise. 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. What makes this role different? You aren’t just a cog in the machine; you’re a mentor and a builder. You’ll have the autonomy to supervise team growth, take full ownership of problem records, and develop self-service tools that empower our people to work smarter.As one of our Senior IT Engineers, you'll:

• 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 like a pro, overseeing MacBooks 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.

We're looking for someone who is:

• 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 PowerShell to replace manual tasks with smart, efficient scripts.

• Experienced in Identity Management, comfortable working primarily with Okta (bonus points for JumpCloud or OneLogin).

• 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.

(We know it's tough, but please try to avoid the confidence gap. You don't have to match all the bullet points above to be considered for this role.)

We encourage people of all different backgrounds and identities to apply. We are committed to maintaining an inclusive, supportive place for you to be you and do your very best work.

Ready to level up our tech?

If you’re a tech-minded pro who lives for automation, clean architecture, and building tools that actually work, we want to hear from you. We’re looking for someone who doesn’t just follow the status quo but looks for ways to refresh and improve our entire stack. If you're ready to take ownership of a high-impact environment where your expertise is valued and your growth is championed, hit the link below. Apply Now!

What Is in It for You?

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.

Employment Practices

Simply Business is an equal opportunity employer. We’re committed to welcoming and helping employees grow within an inclusive & diverse culture.