Senior IT Systems Engineer II, Lead

Job Description

Job Description

Description:

Job Summary

The Senior IT Systems Engineer II, Lead is a senior technical lead with strategic ownership of CaseWorthy's internal IT function — the people, processes, and tools that keep the CaseWorthy workforce productive, secure, and compliant. This role was created to give internal IT a dedicated, hands-on leader, allowing the Director of DevOps & IT to focus on DevOps and platform engineering strategy while the Senior IT Systems Engineer II, Lead owns the day-to-day strategy, roadmap, budget, and team leadership for internal IT.

The Senior IT Systems Engineer II, Lead manages and mentors the IT Support & Operations Engineer team, sets the internal IT roadmap, and is accountable for the two core goals of the CaseWorthy IT function: (1) keeping coworkers productive by resolving issues quickly and proactively preventing recurring ones, and (2) operating IT in strict adherence to the security and compliance frameworks required to pass customer and regulatory audits. The successful candidate blends hands-on technical depth (endpoint management, identity, security tooling) with the operational and people leadership needed to run IT as a mature, metrics-driven service.

Responsibilities

• Own and evolve the internal IT roadmap and strategy in support of the organization's broader business and engineering goals.
• Manage, mentor, and grow the IT Support & Operations Engineer team, including hiring, training, and creating a clear career path.
• Mature, document, and manage the internal IT support program, ensuring tickets are triaged and resolved in a timely manner commensurate with the needs of the business.
• Develop, maintain, and report on key performance indicators (KPIs) for internal IT services, holding the team and supporting vendors accountable to these KPIs.
• Own the security and compliance posture of CaseWorthy's internal IT environment, ensuring policies (patching, endpoint protection, access control) are implemented, enforced, and audit-ready.
• Serve as the escalation point for complex IT support and operations issues, and stay hands-on with tools such as Microsoft Intune, Entra ID, and Windows administration when needed.
• Coordinate with Human Resources to ensure a smooth new-hire and termination process from an IT standpoint (provisioning, deprovisioning, and equipment logistics).
• Develop and manage the internal IT budget, including software/hardware licensing and related IT expenditures, to optimize spend and ensure the company gets the most value.
• Maintain an accurate and up-to-date inventory of all IT assets, and maintain proof of decommissioned assets.
• Develop, propose, and maintain laptop hardware and software standards; manage refresh cycles in accordance with budget.
• Facilitate and manage IT vendor selection, procurement, and onboarding processes.
• Report to the IT Governance Committee monthly on IT vendor performance, progress against IT program goals, and status of ongoing projects.
• Ensure appropriate coverage of support across globally distributed working hours (US and India), and set clear escalation paths to hardware and software vendor support when needed.
• Champion a culture of collaboration, automation, continuous improvement, and shared ownership between IT, DevOps, and security teams.
• Ability to travel nationwide, up to 10% annually.
• Perform other duties as assigned.

Required Skills & Qualifications

• 5+ years of experience in IT operations or IT service management, including 2+ years in a lead, supervisory, or team-management capacity.
• Strong knowledge of IT service management frameworks; ITIL certification is strongly preferred.
• Hands-on experience with the following technologies:
• Microsoft Intune (update and patch management, scripts and remediations, app management).
• Microsoft Entra ID (groups, access management).
• Windows OS administration (patching, performance, security, troubleshooting).
• Ticketing systems (Jira ITSM, ServiceNow, or similar).
• Experience managing IT budgets, vendor relationships, and hardware/software asset lifecycle management.
• Familiarity with security and compliance frameworks (e.g., SOC 2) and supporting tools such as Tenable or other vulnerability management and endpoint protection platforms.
• Strong written and verbal communication skills, with the ability to report to leadership and governance committees.
• Excellent analytical skills, attention to detail, and time management.
• Great cross-team collaboration and problem-solving skills.
• B.S. in IT, Computer Science, or related field, or equivalent experience.

Preferred Skills & Qualifications

• Experience leading a globally distributed IT team across time zones (e.g., US and India).
• Human services or SaaS company background is a plus.
• Familiarity with macOS support and endpoint management.
• Project management experience or certification (PMP, Scrum, or similar).
• Relevant Microsoft certifications (e.g., Endpoint Administrator, Identity and Access Administrator) are a plus.
• M.S. in IT, Computer Science, or related field.