ABOUT THIS 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.WHAT YOU'LL DO
End User & Infrastructure Support
- 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 (may require physical setup/lifting and occasional after-hours work — [confirm and specify])
Automation & Systems Administration
- 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
Identity & Productivity Platforms
- 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
Asset & Lifecycle Management
- Maintain hardware asset records and chain-of-custody documentation
- Manage procurement, deployment, refresh, recovery, and disposal
- Audit inventory for policy compliance
Project Leadership
- Lead medium-to-large IT projects independently (examples: [insert 1–2 representative past projects to calibrate scope, e.g., "office relocation of 150 seats" or "M365 tenant migration"])
- Coordinate across stakeholders and departments
- Produce project plans, documentation, and status reporting
Mentorship & Team Development
- Coach and mentor junior Technical Services Engineers
- Contribute to knowledge base articles and SOPs
- Promote technical best practices across the team
WHAT YOU'LL NEED
- 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
Preferred Qualifications
- 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
ABOUT WAYSTAR
Through a smart platform and better experience, Waystar helps providers simplify healthcare payments and yield powerful results throughout the complete revenue cycle.
Waystar’s healthcare payments platform combines innovative, cloud-based technology, robust data, and unparalleled client support to streamline workflows and improve financials so providers can focus on what matters most: their patients and communities. Waystar is trusted by 1M+ providers, 1K+ hospitals and health systems, and is connected to over 5K commercial and Medicaid/Medicare payers. We are deeply committed to living out our organizational values: honesty; kindness; passion; curiosity; fanatical focus; best work, always; making it happen; and joyful, optimistic & fun.
Waystar products have won multiple Best in KLAS® or Category Leader awards since 2010 and earned multiple #1 rankings from Black Book™ surveys since 2012. The Waystar platform supports more than 500,000 providers, 1,000 health systems and hospitals, and 5,000 payers and health plans. For more information, visit waystar.com or follow @Waystar on Twitter.
WAYSTAR PERKS
- Competitive total rewards (base salary + bonus, if applicable)
- Customizable benefits package (3 medical plans with Health Saving Account company match)
- We offer generous paid time off for our non-exempt team members, starting with 3 weeks + 13 paid holidays, including 2 personal floating holidays. We also offer flexible time off for our 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
Waystar is proud to be an equal opportunity workplace. We celebrate, value, and support diversity and inclusion. Qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, national origin, disability status, genetics, marital status, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.
This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.
Skills Required
- 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
- 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
What We Do
Waystar harnesses the power of agentic AI, generative AI, and advanced automation to drive meaningful outcomes so providers reach peak financial performance and patients receive care with confidence. The Waystar platform is used by more than 1 million providers and supports over 60% of the U.S. patient population - and integrates with all major HIS and practice management systems. The financial and administrative challenges facing healthcare providers are daunting. Waystar’s technology platform simplifies and unifies healthcare payments across the revenue cycle. We empower healthcare organizations to automate manual work, gain insight into processes and performance, and ultimately collect more revenue. At Waystar, we know there’s a better, more efficient way forward. Let’s climb the mountain ahead of us to reach new heights in healthcare.
Why Work With Us
Our Waystar values serve as a compass to center our decisions, inspire action, and promote outstanding performance. We are dedicated to providing a diverse, inclusive workplace and fostering a shared sense of belonging.
Waystar Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
