Lead Technical Support Spec

HMH • Boston, MA

6d • Hybrid

About The Position

As a Lead Technical Support Specialist, you will serve as the primary escalation point for complex technical issues impacting HMH team members. In this role, you will leverage your expertise to deliver advanced troubleshooting, implement effective solutions, manage systems, and ensure the seamless operation of the organization’s technology stack. Success in this position requires a combination of deep technical knowledge, strong problem-solving abilities, exceptional customer service and deskside support skills, and the capability to mentor junior team members.

Requirements

• Bachelor’s degree in computer science, Information Technology, or related field (or equivalent experience).
• At least 5 years of experience in technical support or systems administration within an enterprise environment.
• 3–5 years of hands-on IT support experience, with the ability to solve complex technical issues.
• Advanced proficiency in Windows 10/11 and macOS troubleshooting and support.
• Hands-on experience with Microsoft 365 administration and familiarity with Azure AD/Entra ID.
• Skilled in diagnosing and repairing desktops, laptops, and mobile devices (iOS/Android).
• Solid understanding of TCP/IP, DNS, DHCP, VPN, and wireless connectivity.
• Strong analytical and problem-solving abilities, excellent communication skills, and a customer-focused mindset. Ability to work independently and collaboratively.
• Willing to travel 10–20% of the time.

Nice To Haves

• Industry certifications such as CompTIA A+, Network+, or Microsoft 365 Certified: Modern Desktop Administrator Associate.
• Experience with ITSM platforms (e.g., ServiceNow, Jira).
• Familiarity with scripting languages (PowerShell) for automation.
• Commitment to knowledge sharing and mentoring junior staff.
• Understanding of security and compliance standards.

Responsibilities

• Advanced Technical Support: Act as the primary escalation point for Tier 1 and Tier 2 teams, delivering exceptional “white glove” support to on-site staff. Take full ownership of complex incidents and service requests, ensuring timely resolution in alignment with established SLAs.
• Hardware Management: Oversee the installation, configuration, troubleshooting, and repair of desktops, laptops (Windows and macOS), printers, and peripherals. Manage the full device lifecycle, including imaging, deployment, and decommissioning.
• Software & OS Expertise: Provide advanced support for Windows 10/11 and macOS environments, as well as enterprise applications such as Microsoft 365 (Outlook, Teams, OneDrive, SharePoint Online, and Office suite).
• Endpoint Management: Utilize modern endpoint management tools (Microsoft Intune, JAMF) for device enrollment, compliance enforcement, configuration profiles, and application deployment.
• Documentation & Process Optimization: Create and maintain technical documentation, including SOPs and knowledge base articles. Identify and implement process improvements to enhance efficiency and user experience.
• Project Engagement: Contribute to IT initiatives such as hardware refreshes, office setups, and system upgrades. Lead small-scale projects as needed.
• Vendor Coordination: Collaborate with third-party vendors and service providers for equipment repairs and product evaluations.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 1,001-5,000 employees