Information Technology Manager

This role will lead and support our technology infrastructure across multiple New England locations and in Montana and North Dakota. Under the general supervision of the Director of Operations, you will oversee a dedicated team of IT Technicians and an IT Technician Lead. In this role, you will ensure operational excellence, maintain robust system security, and guide our technology roadmap to support long-term growth, efficiency, and mission delivery. This individual would be based out of the 69 Grove Street, Worcester, MA location but will be required to travel throughout New England. WHAT YOU’LL BE RESPONSIBLE FOR DAY TO DAY:

• Team Leadership & Vendor Management: Direct, mentor, and evaluate IT staff to foster accountability. Manage ticketing workflows and regional coverage (New England, MT, ND). Serve as primary contact for ISPs, telecom, and mobile vendors. Review service level agreements (SLAs) and optimize recurring contracts.
• Technical Support & Field Operations: Provide multi-channel technical support (in-person, phone, email, remote). Travel to regional sites for cabling, hardware installation, and setups. Oversee full-lifecycle asset tracking and hardware/software inventory.
• Systems Administration & Infrastructure: Configure and maintain Azure AD, Office 365, Intune, and UniFi. Monitor network performance, CCTV networks, and managed services (ConnectWise). Manage infrastructure vendors like Connectivity Point, T-Mobile, and Verizon.
• Cybersecurity, Compliance & Documentation: Enforce multi-location security policies and monitor active threats. Administer EDR and Check Point Harmony email security tools.

Lead incident response strategies and staff security awareness training. Maintain network diagrams and infrastructure maps, and ensure licensing compliance.

• Strategic Planning & Budgeting: Align long-term IT strategy with corporate growth goals. Prepare and manage the annual IT budget. Conduct cost-benefit analyses for emerging technology investments.

• Bachelor’s degree in information technology, Computer Science, or a related field (Master’s degree preferred).
• Five plus years of verified IT experience, including a minimum of 3 years in a formal leadership or supervisory capacity.
• Demonstrated experience supporting distributed IT infrastructure across a multi-site organization or working within the nonprofit sector.
• Must travel regularly to Veterans Inc. locations across New England. Must have a valid driver’s license and own reliable transportation.

Comprehensive Benefits Package for FT employees includes:

• BCBS Medical, Dental, and Vision Insurance
• Employer Paid Short and Long-Term Disability and Life Insurance.
• $2,500 Medical Opt-Out program if you have medical coverage through another source.
• Retirement Plan (403B) with a $3,000 Match
• Flexible Spending Accounts
• Tuition Reimbursement Program
• Paid Parental Leave

Veterans Inc. is a premier non-profit organization dedicated to ending veteran homelessness and inspiring 100,000+ veterans and their families across New England, Montana, and North Dakota to achieve long-term self-sufficiency. As a national leader in veteran services, we are currently seeking a dynamic IT Manager who will lead our technology infrastructure, secure our digital assets, and optimize the systems that empower our frontline teams to deliver immediate resources to our nation’s heroes., Company Description Pilot Company is an industry-leading network of travel centers with more than 30,000 team members and over 750 retail and fueling locations in 44 states and s…