Desktop Support Specialist

Role Details

Job Title: Desktop Support Specialist

Location: Wakefield, MA (onsite 5 days in the office)

Reports To: Information Technology Manager

Employment Type: Full time

Job Requisition ID: 2026-538

Requisition Begin Date: 06/03/2026

Help us insure it

Tokio Marine HCC is a global industry-leading specialty insurance group, backed by the strength and stability of the Tokio Marine Group. Offering over 100 classes of specialty insurance, we empower clients to pursue opportunities confidently through our “Mind Over Risk” philosophy. More than an insurance company, we are an organization built on innovation, unity, and trust.

At our core, we are Always Advancing, driven by innovation and an entrepreneurial spirit that keeps us moving forward. Our people are Experts in Tomorrow, using curiosity and smart working to anticipate what’s next. With a culture rooted in Reaching Out, we foster genuine collaboration and support, ensuring every individual has the opportunity to succeed and make a difference.

Role Overview

• Within the first 90 days, you will learn about our business, systems, procedures, local and corporate staff by closely shadowing the IT Technology Manager.

• Within the first 6 months, you will provide:

• Second tier support to end users (ranging from support staff to the Chairman), in a Windows 11 and Office 365 environment, using MS Teams.

• Maintain multiple Windows Server machines, WAN/LAN systems, printers, and security-related patches, as well as become the point person for any facility-related requests.

• By the end of the first 6 months, you will work independently and have developed and demonstrated a working relationship with users at all technical ability levels and IT staff (local and offsite). This position is multifaceted and requires you to balance time with other responsibilities.

• Ongoing, You will be responsible for creating and maintaining documentation related to IT procedures.

Travel expectations

• Travel (less than 10%) to other TMHCC locations (Salem, NH and Chappaqua, NY) will be required.

What You Bring

• You have an associate degree in computer science or a related field or the equivalent education and/or experience

• You possess up to two years of relevant and progressive professional desktop support experience, working in an office environment

• You can demonstrate excellent analytical and critical thinking skills

• You are highly organized and pay close attention to detail

• You have a strong proficiency in Office 365

• You must have excellent written and verbal communication skills

You will stand out if you have obtained any combination of the following:

• CompTIA A+ Certification

• ITIL Foundation Certification

• Microsoft Certified Systems Administrator (MCSA) for Windows 11 or later

If this position sounds like a perfect fit, please apply WITH A COVER LETTER, expressing why you want to join our team.

What We Offer

• Competitive salary and comprehensive benefit package

• Strong learning culture with ongoing development opportunities

• Opportunities for growth and career advancement

• Comprehensive medical, vision, and dental coverage, with eligibility beginning on your first day of employment

• Basic life and disability insurance

• 401(k) plan with 6% company match

• 20 days of PTO, two floating holidays, approximately 11 paid holidays, and volunteer time off

• Paid parental leave

• Access to our award-winning wellness program, including mental health services, fitness network membership, and a complimentary Headspace subscription

• Student loan matching program

• Employee discount program

• An opportunity to do meaningful work and love what you do

Pay Transparency

The pay range for this position is $28.08 - $38.60 per hour, which includes geographic adjustments, where applicable. The pay range is the range THMCC, in good faith, believes is the range of compensation for this role at the time of this posting. The hired applicant will be offered pay within the entire range based on the candidate’s geographic location, qualifications, work experience, education, and/or skill level. The Company is fully committed to ensuring equal pay opportunities for equal work regardless of color, race, sex, national origin, sexual orientation, religion, age, veteran status, disability, pregnancy, citizenship status, genetic information, or any other basis protected by federal, state, or local pay equity laws.

Disclaimer

As an insurance company, we comply with certain federal, state and local laws such as the Violent Crime Control and Law Enforcement Act of 1994 (18 USC § 1033(e)), which restricts our ability to employ individuals with certain types of criminal convictions. Where not restricted by law and for criminal history not covered by this law, the Company will consider qualified applicants with arrest or conviction history in compliance with applicable law.

About Us

Tokio Marine HCC is a leading specialty insurance group with offices in the United States, the United Kingdom, Europe, and other exciting locations. With the strength and stability that comes from being a member of the Tokio Marine Group, and more than fifty years of growth, profitability, and stability, we offer important insurance products that most people don’t even know exist. Every policy we write is special, enabling our clients to do amazing things.

Tokio Marine HCC - Specialty Group, a member of the Tokio Marine group of companies, is a market leader in providing specialized insurance products for the sports, entertainment, and promotional industries. We provide an unmatched portfolio of products including event cancellation, high limit disability, kidnap and ransom, weather, travel, event liability and much more. We cover major sports and entertainment events, professional athletes and entertainers and other unique assets.

Applying our Mind Over Risk philosophy to writing insurance allows our customers to take on opportunity with confidence. That philosophy defines our way of thinking, unites us as a team, and differentiates us from our competitors. We are much more than just an insurance company; we are a good company.

Equal Opportunity Employer

TMHCC is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, citizenship, color, family or medical care leave, gender identity, genetic information, marital status, medical condition, national origin, physical or mental disability, protected veteran or military status, race, ethnicity, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable local laws, regulations and ordinances.

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