IT Sr. Systems Support Specialist

Brief Overview

The Senior IT Systems Support Specialist supports the company’s corporate IT infrastructure, including Windows and macOS devices, mobile devices, Microsoft 365, telephony, servers, networks, and related systems.

This is a hands-on role focused on endpoint deployment and management using NinjaOne, Microsoft Intune, and Windows Autopilot. The position requires an experienced IT professional who can work independently, resolve complex issues, manage projects, serve as a technical escalation point, and mentor junior team members.

Although this is not a cybersecurity role, the Specialist must follow and reinforce established security baselines in daily IT operations.

Core Responsibilities

• Administer Windows and macOS devices, applications, deployment profiles, policies, and patches using NinjaOne, Intune, and Autopilot.
• Support the IT Help Desk function serving more than 1,000 end users.
• Troubleshoot complex endpoint, Microsoft 365, account, authentication, network, and application issues.
• Manage Active Directory users, groups, permissions, and Microsoft Entra ID accounts.
• Support Exchange Online, Outlook, Teams, SharePoint, OneDrive, calendars, and distribution groups.
• Manage IT infrastructure projects from planning through implementation, documentation, and ongoing support.
• Serve as a technical escalation point and mentor junior IT team members.
• Ensure timely resolution of approximately 75 or more tickets per month and completion of two or more projects per quarter.
• Participate in an after-hours on-call rotation approximately once every eight weeks.
• Support endpoint protection and vulnerability-management platforms, preferably Sophos Central and Rapid7.
• Assist with IT asset management, device lifecycle management, and inventory control.
• Represent IT professionally in meetings with employees, executives, vendors, and clients.

Required Technical Experience

• 5+ years of hands-on experience supporting and managing Windows and macOS environments.
• Windows 10 and Windows 11 administration and troubleshooting.
• macOS administration and command-line troubleshooting.
• Operating system, application, policy, and patch deployment.
• NinjaOne, Microsoft Intune, and Windows Autopilot.
• Active Directory, Microsoft Entra ID, MFA, and single sign-on.
• Microsoft 365 administration and end-user support.
• PowerShell scripting and administration.
• Basic networking knowledge, including TCP/IP, DNS, DHCP, VPN, and SSL/TLS.
• Endpoint security, disk encryption, and device-compliance controls.
• Strong verbal and written English skills (B2+ or above)

Qualifications

• Strong troubleshooting, analytical, and critical-thinking skills.
• Ability to work independently and manage projects from beginning to end.
• Strong understanding of endpoint security, patching, access control, and IT best practices.
• Excellent written and verbal communication skills.
• English proficiency at the B2 level or higher.
• Ability to support a 24/7 organization and participate in an on-call rotation.
• Ability to travel to local corporate offices when required.
• Must be legally authorized to work without employer sponsorship.

Preferred Qualifications

• Microsoft certifications or current Microsoft role-based certifications.
• Experience with Sophos Central, Rapid7, BitLocker, and FileVault.
• Experience supporting more than 1,000 users.
• Previous experience mentoring junior IT professionals.

Do Well. Live Well. At Amwell.

Driven by our mission and values, we foster a workplace where Delivering Awesome, being Customer First and operating as One Team aren’t just aspirations – they are how we work, every day.

Our people are our greatest asset. We strive to empower their growth and development not only as Amwellians but as individuals, through generous total rewards packages, a virtual-first work environment, work-life flexibility, including Summer Fridays and designated Mental Health Days, as well as opportunities to stretch and learn – to name a few. It’s our people who truly differentiate us. Ask anyone and they’ll tell you – you’ll never work with more passionate, more driven and more caring team members.

We champion a culture of respect and inclusion, accountability and integrity, innovation and collaboration. At Amwell, you’ll do the most meaningful work of your career—improving healthcare for millions, growing alongside incredible teammates, and being valued for who you are.

Working at Amwell:

Amwell is changing how care is delivered through online and mobile technology. We strive to make the hard work of healthcare look easy. In order to make this a reality, we look for people with a fast-paced, mission-driven mentality. We’re a culture that prides itself on quality, efficiency, smarts, initiative, creative thinking, and a strong work ethic.

Our Core Values include One Team, Customer First, and Deliver Awesome. Customer First and Deliver Awesome are all about our product and services and how we strive to serve. As part of One Team, we operate the Amwell Cares program, which brings needed assistance to our communities, whether that be free healthcare for the underserved or for people affected by natural disasters, support for equality, honoring doctors and nurses, or annual Amwell-matched donations to food banks. Amwell aims to be a force for good for our employees, our clients, and our communities.

Amwell cares deeply about and supports Diversity, Equity and Inclusion. These initiatives are highlighted and reflected within our Three DE&I Pillars - our Workplace, our Workforce and our Community!

Benefits

Additional Benefits

• Medical Plan Coverage provided by Colmédica
• Plan Coverage provided by Pan American
• Additional Paid Time Off
• Maternity Leave 18 weeks
• Parental/Paternity Leave 2 mandatory weeks + 4 weeks
• Mental Health and Resiliency
• Virtual Second Opinion with the Cleveland Clinic Coverage
• LinkedIn Learning
• Rewards and Recognition
• Service Anniversaries
• Annual Bonus
• Referral Program
• Amwell tuition reimbursement benefit

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