Fast Facts

The Lead Technical Support Specialist will provide advanced technical support and manage the organization's technology stack, ensuring seamless operation and mentoring junior team members.

Responsibilities: Key responsibilities include delivering advanced troubleshooting, overseeing hardware management, providing software and OS expertise, creating documentation, and engaging in IT projects and vendor coordination.

Skills: Proficiency in Windows 10/11 and macOS troubleshooting, Microsoft 365 administration, endpoint management tools, and excellent problem-solving and customer service skills are required.

Qualifications: A Bachelor's degree in computer science or related field and at least 5 years of experience in technical support or systems administration are preferred, along with industry certifications and familiarity with ITSM platforms.

Location: This position is hybrid and based in Boston, MA, with travel required 10-20% of the time.

Compensation: $80000 - $100000 / Annually

Job Title:Lead Technical Support Specialist

Location:Hybrid, Boston

Who We Are

HMH is a learning technology company committed to delivering connected solutions that engage learners, empower educators and improve student outcomes. As a leading provider of K–12 core curriculum, supplemental and intervention solutions, and professional learning services, HMH partners with educators and school districts to uncover solutions that unlock students’ potential and extend teachers’ capabilities.

HMH serves more than 50 million students and 4 million educators in 150 countries. HMH is focused on developing novel products and solutions using cutting-edge technology to better serve our clients globally. HMH aims to help employees grow as people, and not just as professionals. For more information, visit www.hmhco.com.

What You’ll Do

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. 

Key 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 You’ll Need

• 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.

Preferred Qualifications:

• 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.

Physical requirements:

• Might be in a stationary position for a considerable time (sitting and/or standing).
• Constantly operates a computer and other digital devices.
• Ability to collaborate via online meetings and work in cross-functional teams.

Salary Range: $80k – 100k.

Application Deadline:

The application window for this position is anticipated to close on January 19, 2026. We encourage you to apply as soon as possible. The posting may be available past this date but is not guaranteed.

HMH is fully committed to Equal Employment Opportunity and to attracting, retaining, developing and promoting the most qualified employees without regard to race, gender, color, religion, sexual orientation, family status, marital status, pregnancy, gender identity, ethnic/national origin, ancestry, age, disability, military status, genetic predisposition, citizenship status, status as a disabled veteran, recently separated veteran, Armed Forces service medal veteran, other covered veteran, or any other characteristic protected by federal, state or local law. We are dedicated to providing a work environment free from discrimination and harassment, and where employees are treated with respect and dignity. We actively participate in E-Verify.

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