Sr Technical Services Engineer I

Waystar, Inc; Louisville (KY); On-site; USD 110,000 - 140,000; Full time

Benefits offered by this job

Competitive total rewards (base salary

Generous paid time off

Parental leave

Education assistance

Mental health programs

401(K) with company match

Pet insurance

Employee resource groups

Job summary

Waystar is seeking a Sr. Technical Services Engineer I to serve as a senior escalation resource providing advanced endpoint, OS, and collaboration technology support across company locations.

You will own complex incidents, coordinate vendor activities, and contribute to standards and knowledge sharing. You will lead medium-sized Technical Services initiatives, manage asset lifecycle, and support executive meetings with proactive device management and rapid issue resolution.

Qualifications

• 5+ years of progressive IT support, desktop support, field services, endpoint support, technical services, or related technical operations experience.
• Experience resolving highly complex end-user technology issues and coordinating cross-functional technical escalations.

Responsibilities

• Serve as a senior escalation resource for complex endpoint, OS, Microsoft 365, mobile device, identity and access, network connectivity, enterprise applications, and collaboration technology issues.
• Own assigned issues through resolution, coordinating technical resources, vendors, communications, and follow-up activities.
• Lead medium-size Technical Services projects or defined workstreams within broader enterprise technology initiatives.
• Provide senior-level support for endpoint deployment, configuration, maintenance, compliance, software delivery, OS lifecycle, and technology refresh activities.
• Develop clear technical findings and recommendations to support durable solutions and reduce repeat incidents.

Skills

Executive support

Endpoint management

Windows

macOS

Microsoft 365

ITIL knowledge

Jira Service Management

Travel

Education

Associate's or Bachelor's degree in Information Technology or related field

Tools

Microsoft Intune

Jamf

SCCM

Jira Service Management

Job description

ABOUT THIS POSITION

The Sr. Technical Services Engineer I serves as a senior technical resource within the Technical Services organization, providing advanced Tier 2 support, executive technology services, workplace technology support, and technical project delivery across company locations. This role independently resolves highly complex issues, owns assigned technical domains and service responsibilities, coordinates incident and vendor escalation activities, and leads medium-sized Technical Services initiatives. The Sr. Technical Services Engineer I provides technical guidance to less-experienced engineers and contributes to standards, documentation, and continuous improvement while remaining an individual contributor without day-to-day operational team leadership or formal people management responsibilities.

WHAT YOU'LL DO

Advanced Technical Support & Escalation

Serve as a senior escalation resource for complex endpoint, operating system, Microsoft 365, mobile device, identity and access, network connectivity, enterprise application, and collaboration technology issues. Perform advanced troubleshooting, root cause analysis, and problem resolution for recurring, high-impact, or technically complex incidents. Own assigned issues through resolution, coordinating technical resources, vendors, communications, and follow-up activities as needed. Develop clear technical findings and recommendations that support durable solutions and reduce repeat incidents. Coordinate troubleshooting and escalation with Infrastructure, Security, Corporate Systems, IT Support, and external service partners. Participate in the Technical Services on-call rotation and provide senior escalation support during service disruptions.

Executive & High-Touch Technology Support

Provide white-glove technical support for executive leadership and other critical business stakeholders. Deliver proactive device management, meeting readiness, rapid issue resolution, and clear communication for executive technology needs. Support executive meetings, board meetings, town halls, and major company events through preparation, testing, live troubleshooting, and follow-up. Partner with Executive Assistants, Facilities, Security, and business stakeholders to ensure technology readiness in executive offices and shared spaces. Identify opportunities to improve the consistency, reliability, and experience of executive technology support.

Endpoint, Workplace Technology & Technical Domain Ownership

Provide senior-level support for endpoint deployment, configuration, maintenance, compliance, software delivery, operating system lifecycle, and technology refresh activities. Own assigned technical service areas, platforms, locations, or operational responsibilities and maintain associated standards and documentation. Support and improve conference rooms, audio-visual systems, digital signage, printing, collaboration technologies, and other workplace technology services. Coordinate technology readiness across company locations, including offices, shared spaces, high-priority meetings, and company events. Partner with Workplace Experience, Facilities, Security, and vendors on office technology issues, deployments, upgrades, and modernization efforts. Travel occasionally to support company locations, technology deployments, or service needs.

Asset Lifecycle & Operational Excellence

Provide senior oversight and execution for hardware and software lifecycle activities, including procurement support, inventory, deployment, maintenance, recovery, refresh, and retirement. Ensure asset management records, chain-of-custody documentation, and software licensing information are accurate and compliant with established procedures. Support the technical execution and continuous improvement of employee onboarding, role change, and offboarding processes. Review recurring operational tasks, maintenance activities, audits, and readiness checks for quality, consistency, and effectiveness. Identify operational risks, service gaps, technical debt, and standardization opportunities and recommend corrective action.

Project & Initiative Leadership

Lead medium-size Technical Services projects or defined workstreams within broader enterprise technology initiatives. Plan and coordinate project activities, resources, timelines, dependencies, testing, deployment, documentation, user readiness, and post-implementation support. Lead or support endpoint refresh programs, office technology deployments, workplace modernization efforts, executive technology initiatives, and new tool rollouts. Communicate project status, risks, decisions, and implementation impacts to Technical Services leadership and project stakeholders. Serve as a technical resource for enterprise projects requiring Technical Services participation. Balance project commitments with operational support responsibilities and established service objectives.

Knowledge Management, Standards & Continuous Improvement

Create, review, and maintain advanced technical documentation, knowledge base articles, standard operating procedures, support standards, and troubleshooting guides. Analyze incident patterns, support trends, user feedback, and system failures to identify opportunities for sustainable improvement. Recommend and contribute to automation, workflow, tooling, and standardization initiatives that improve quality, efficiency, and user experience. Promote consistent troubleshooting, escalation, documentation, asset management, and customer communication practices across Technical Services. Provide technical guidance, knowledge sharing, and informal mentorship to Technical Services Engineer I and II team members. Contribute technical input to service planning, roadmap discussions, annual goal planning, and operational improvement priorities.

Customer Experience & Cross-Functional Partnership

Deliver professional, responsive, and customer-focused support through proactive communication, clear expectations, ownership, and timely follow-up. Build productive partnerships with IT Support, Infrastructure, Security, Corporate Systems, Workplace Experience, Facilities, Executive Assistants, and business stakeholders. Coordinate vendor troubleshooting, repair, upgrade, and implementation activities and hold service partners accountable for assigned deliverables. Represent Technical Services in technical discussions, project meetings, service reviews, and operational planning activities when assigned. Communicate technical risks, recurring service concerns, and improvement recommendations to Technical Services leadership.

WHAT YOU'LL NEED

Required Qualifications

5+ years of progressive IT support, desktop support, field services, endpoint support, technical services, or related technical operations experience. Demonstrated success resolving highly complex end-user technology issues and coordinating cross-functional technical escalations.

Preferred Qualifications

Experience providing white-glove support to executive leadership or supporting high-priority meetings and company events. Experience owning a technical service, platform, location, or operational domain. Experience coordinating vendors and cross-functional technology teams during incidents or project implementations. Experience creating technical standards, procedures, knowledge articles, training materials, or service documentation. Familiarity with ITIL principles, incident management, problem management, and service management best practices. CompTIA, Microsoft, Apple, ITIL Foundation, project management, or equivalent certifications preferred. Associate's or Bachelor’s degree in Information Technology or a related field, or equivalent practical experience. Advanced working knowledge of Windows, macOS, Microsoft 365, mobile devices, identity and access platforms, endpoint technologies, and collaboration tools. Experience with endpoint management platforms such as Microsoft Intune, Jamf, SCCM, or equivalent. Experience supporting workplace technology, conference room A/V systems, distributed users, and company office locations. Experience leading technical projects or defined workstreams involving deployments, upgrades, refreshes, or process improvements. Experience using Jira Service Management or a similar ITSM platform in an SLA-driven environment. Strong analytical, root cause analysis, troubleshooting, organizational, and decision-making skills. Excellent written and verbal communication skills, including communication with executive and nontechnical audiences. Ability to work independently, manage competing priorities, mentor peers, participate in an on-call rotation, and travel occasionally.

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

Equal Opportunity Statement

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.