Service Desk Engineer

SB2 Simply Business, LLC; Boston (MA); Hybrid; USD 62,000 - 103,000; Full time

Benefits offered by this job

Medical, dental, vision coverage

401(k) with 5% employer match

Commuter benefits

Vacation and sick days

Job summary

Simply Business, a digital insurance brokerage, is seeking an IT Service Desk professional to deliver reliable support across a Cloud/SaaS environment. You’ll handle first-line inquiries for BizOps IT, with opportunities to improve self-service and automation.

The role focuses on ensuring smooth operations for ChromeOS, Windows, and macOS, in a hybrid work setting with a strong emphasis on customer experiences and culture.

Qualifications

• Experience in 1st line service desk or desktop support.
• Strong hands-on and face-to-face desktop support experience.
• Familiarity with IT Service Management (ITSM) best practices.

Responsibilities

• Serve as the first point of contact for IT questions and incidents during core business hours.
• Provide hands-on and remote IT support to employees across the US and UK.
• Log, categorize, acknowledge, and resolve incidents and service requests.

Skills

1st line service desk

Desktop support

Troubleshooting

ITSM familiarity

Team collaboration

Job description

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 Category

Technology

Position Type

Permanent

Compensation 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

$62,300.00 - $102,800.00

Target Openings

1

What Is the Opportunity?

About the Role You’ll be part of a dynamic IT Service Desk team delivering simple, intuitive, and hassle-free IT support across Simply Business. You’ll ensure our team members have reliable systems and keep our technology running seamlessly every day. You will report directly to Aaron, Global Service Desk Lead, who works closely with the team to provide top-class support within our full Cloud/SaaS infrastructure environment (supporting ChromeOS, Windows, and macOS).

Key Responsibilities

• Day-to-Day Support: Act as the first point of contact for all BizOps IT questions, queries, and incidents via official support channels, ensuring timely responses during core business hours.
• Global Support: Provide hands-on and remote IT troubleshooting and support to Simply Business employees across both the UK and the US.
• Incident Management: Ensure all incidents and service requests are correctly logged, categorized, acknowledged, and resolved in line with incident management and request fulfillment processes.
• Access & Lifecycle Management: Manage Joiners, Movers, and Leavers (JML), including identity and access management for existing and departing staff.
• AV & Facilities Support: Support audio-visual meeting room equipment, escalating complex issues when necessary.
• Operational Administration: Maintain stock levels through quarterly Business-As-Usual (BAU) reviews, conduct regular housekeeping audits, and complete routine administrative duties in accordance with established IT processes.
• Continuous Improvement: Help drive self-service initiatives, automation, and end-user empowerment across the business.

What We’re Looking For

Experience & Passion

Demonstrated experience in or a strong passion for 1st line service desk / desktop support.

Problem-Solving Skills

Strong hands-on and face-to-face desktop support experience with a structured, logical approach to troubleshooting.

Culture & Growth Mindset

Willingness to help elevate the BizOps IT team and actively contribute to positive cultural and process changes.

Process Awareness

Familiarity with IT Service Management (ITSM) best practices, ticket management, and service request fulfilment.

What Is in It for You?

• 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.

At Simply Business, we insure small businesses and enable big dreams. Not just for our customers, but for our people, our communities and our environment. We believe a world-class company culture is crucial to achieving our business goals as we make insurance more accessible to small business owners. We’re building a better way to buy small business insurance, and we’re using technology to get the job done. That includes developing cutting-edge data gathering and analysis capabilities; living and breathing testing and experimentation; and harnessing the many benefits of AI and other emerging technologies. We’re a values-led business. Our people all have a part to play in building a culture that lives these values: learning, empowerment, authenticity, pioneering, and simplicity.