Sr. Technical Services Engineer I

Waystar, Inc; Louisville (KY); On-site; USD 95,000 - 125,000; Full time

Benefits offered by this job

Competitive total rewards

Generous PTO and holidays

401(k) with matching

Education assistance

Employee assistance programs

Job summary

Waystar is seeking an experienced Specialist Technical Services Engineer to join the Enterprise Technology team in Louisville, KY. This senior individual-contributor role blends advanced end-user support, automation, systems administration, asset lifecycle management, and project execution.

The role acts as a technical mentor to junior engineers and leads workplace technology initiatives, with responsibilities spanning onboarding, lifecycle activities, and IT project leadership.

Qualifications

• 5+ years of IT support experience including hardware deployment and troubleshooting.
• Hands-on administration with Active Directory, Microsoft Entra ID, and Microsoft 365.
• Experience building automation/tools with PowerShell and/or Python.
• Experience consuming REST APIs for system integration.
• Proven ability to lead IT projects independently.
• Mentored or coached junior team members.

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 for reporting, provisioning, device management, and admin workflows.
• Administer authentication platforms and identity initiatives (AD, Entra ID, 365).
• Lead medium-to-large IT projects and coordinate with stakeholders.
• Mentor junior Technical Services Engineers and contribute to SOPs.

Skills

IT support

Active Directory

PowerShell/Python

REST APIs

Project leadership

Mentoring

Communication

Education

Bachelor's degree in IT/CS

Tools

Jira Service Management

Job description

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. Waystar provides cloud-based technology that simplifies and unifies healthcare payments. Together, our technology, data and client support streamline workflows and improve financials for our clients, so that they can focus on their patients. 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 and fun.