Sr. Technical Services Engineer I

WaystarLouisville, KY

About The Position

We are seeking an experienced, technically skilled Specialist Technical Services Engineer to join our Enterprise Technology team. This is a senior individual-contributor role combining advanced end-user support, automation/scripting, systems administration, asset lifecycle management, and project execution. The role also serves as a technical mentor to junior engineers and a lead for workplace technology initiatives.

Requirements

  • 5+ years of IT support experience, including hardware deployment and troubleshooting
  • Hands-on administration experience with Active Directory, Microsoft Entra ID, and Microsoft 365
  • Demonstrated experience building automation/tooling with PowerShell and/or Python
  • Experience consuming REST APIs for system integration
  • Track record independently leading and delivering IT projects
  • Demonstrated experience mentoring or coaching junior team members
  • Strong troubleshooting and problem-solving skills
  • Excellent verbal and written communication skills

Nice To Haves

  • Experience with asset management/inventory platforms and chain-of-custody documentation
  • Familiarity with Jira Service Management or similar ITSM tooling
  • Experience supporting AV/conferencing and workplace technology systems
  • Bachelor's degree in IT, Computer Science, or equivalent experience

Responsibilities

  • Provide advanced Tier 2/3 support for hardware, software, OS, and enterprise applications
  • Troubleshoot complex issues across desktops, laptops, mobile devices, printers, conferencing systems, and collaboration platforms
  • Own onboarding, offboarding, equipment deployment, office moves, and lifecycle activities
  • Build and maintain automation using PowerShell and/or Python
  • Develop tools for reporting, provisioning, device management, and admin workflows
  • Integrate systems via REST APIs
  • Proactively identify manual processes for automation
  • Administer Active Directory, Microsoft Entra ID, and Microsoft 365 (Exchange Online, Teams, OneDrive, SharePoint)
  • Manage account provisioning, access control, licensing, and security-related tasks
  • Support enterprise authentication and identity initiatives
  • Maintain hardware asset records and chain-of-custody documentation
  • Manage procurement, deployment, refresh, recovery, and disposal
  • Audit inventory for policy compliance
  • Lead medium-to-large IT projects independently
  • Coordinate across stakeholders and departments
  • Produce project plans, documentation, and status reporting
  • Coach and mentor junior Technical Services Engineers
  • Contribute to knowledge base articles and SOPs
  • Promote technical best practices across the team

Benefits

  • Competitive total rewards (base salary + bonus, if applicable)
  • Customizable benefits package (3 medical plans with Health Saving Account company match)
  • Generous paid time off for non-exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays
  • Flexible time off for exempt team members + 13 paid holidays
  • Paid parental leave (including maternity + paternity leave)
  • Education assistance opportunities and free LinkedIn Learning access
  • Free mental health and family planning programs, including adoption assistance and fertility support
  • 401(K) program with company match
  • Pet insurance
  • Employee resource groups
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