ABOUT THIS POSITION
The Sr Systems Engineer II is a senior technical leader responsible for designing, implementing, and governing enterprise wide systems that support reliable, secure, and scalable business operations. This role requires deep expertise across mail systems, cloud services, virtualization, backups, and enterprise change governance. The ideal candidate brings at least 10 years of hands-on experience in systems administration and end user support, with the ability to translate complex technical requirements into actionable architectural strategies.WHAT YOU'LL DO
- Architect, design, and maintain enterprise systems across cloud and on‑prem environments, with a focus on reliability, security, and scalability.
- Serve as a technical authority on mail protocols and routing, including SMTP, DMARC, DKIM, SPF, transport rules, message hygiene, and mail flow analysis.
- Lead and influence architectural decisions across Microsoft Azure and Microsoft 365 ecosystems.
- Act as a core member of the Technical Change Approval Board, providing expert review on change requests, risk assessments, and cross‑system impact analysis.
- Develop and enforce technical standards, documentation, and operating procedures.
- Support modernization and automation initiatives to improve operational efficiency.
- Partner with cross‑functional teams—including Security, Helpdesk, Tech Services, SaaS, and others—to ensure architectural alignment across the enterprise.
- Troubleshoot complex multi‑system issues with a methodical and data‑driven approach.
- Mentor engineers and contribute to long‑term capability building across the department.
WHAT YOU'LL NEED
- 10+ years of progressive experience in systems administration and end‑user support.
- Deep technical knowledge of email protocols, routing, and infrastructure, including:
- SMTP, IMAP, POP
- Transport routing and mail hygiene systems
- Authentication frameworks such as SPF, DKIM, DMARC
- Strong experience with Microsoft Azure, including:
- Identity & Access Management (Entra ID)
- Infrastructure services (VMs, networking, storage)
- Azure automation
- Extensive expertise in Microsoft 365 administration, including:
- Exchange Online
- Teams & SharePoint administration
- Compliance, DLP, and tenant configuration
- Strong understanding of enterprise change management processes; experience reviewing, approving, or governing complex changes.
- PowerShell scripting, automation tools, or infrastructure‑as‑code platforms.
- Proven ability to lead cross‑disciplinary architecture discussions and drive consensus.
- Excellent documentation, communication, and stakeholder engagement skills.
Preferred Skills:
- Backup platforms such as Rubrik (or comparable enterprise solutions).
- Virtualization technologies, ideally VMware vSphere, but equivalent platforms are also welcome.
- Experience in hybrid cloud or multi‑cloud architectures.
- Familiarity with security standards and compliance frameworks.
- Strong analytical thinking and root‑cause analysis abilities.
- Adaptability to rapidly evolving technology landscapes.
- Collaboration‑focused mindset and a willingness to guide others.
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.
What We Do
Waystar provides market-leading technology that simplifies and unifies healthcare payments. Our cloud-based platform streamlines workflows and improves financials for healthcare providers of all kinds, and brings more transparency to the patient financial experience. The Waystar platform is used by more than 450k providers, 750 health systems and hospitals, and 5k health plans—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.
Waystar Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
