Checkwriters is looking for an IT Support Specialist to work alongside our IT Director! We offer a competitive salary and benefits package, Paid Time Off, a comfortable, convenient, and state-of-the-art office, and company-sponsored social events. This is an in-office position at our Northampton, MA location. If you are good at problem solving, capable of taking on challenges, and enjoy working with others, this could be an excellent position for you! Checkwriters is a payroll and HR services company focused on elevating every step of the customer experience. From interactions with our team to genuinely useful Payroll and HR software — we don't just provide an excellent product. We have a team of experts who care about the details, and work continuously to ensure that we provide our customers with the best experience they've had with a payroll and HR provider. On a typical day you will: Serve as the first point of contact for internal IT support, troubleshooting hardware, software, system access, and connectivity issues. Manage employee user accounts and access, including onboarding, role changes, and offboarding. Set up, configure, maintain, and troubleshoot computers, mobile devices, printers, conference room equipment, and other technology. Support the security and reliability of company technology, including system updates, endpoint security, and phishing reports. Maintain and support office technology and critical payroll/check-printing equipment to minimize downtime and disruption. Maintain accurate hardware, software, licensing, and equipment inventory and documentation. Travel to client locations as needed to install, configure, and maintain time clocks and other IT equipment. Assist with the testing, implementation, and rollout of new technology and other IT initiatives Our ideal candidate will have: 3+ years of experience in help desk, desktop support, or a similar IT support role. Relevant IT certifications , such as CompTIA or Microsoft certifications. Working knowledge of Windows, Microsoft 365, Active Directory/Entra ID, and common business technologies. Experience with ticketing, remote monitoring, and device management tools. Understanding of basic networking. system security, and hardware troubleshooting. Experience supporting technology in a regulated, audited, financial services, or payroll environment. Strong technical troubleshooting and problem solving skills with the ability to manage multiple priorities. Excellent communication and customer service skills.