SYSTEMS ENGINEER

About WIN

At WIN, we believe everyone deserves expert, compassionate support through every stage of family life. From preconception and fertility to pregnancy, parenting, menopause, caregiving, and beyond, we’re transforming how people access care during life’s most meaningful moments.

For nearly 30 years, we’ve partnered with employers, health plans, and providers to improve outcomes, lower healthcare costs, and support more than 900,000 families around the world.

We're investing in our products, our people, and the future of well-being—and we're looking for teammates who are excited to help shape what's next.

The Opportunity

WIN is seeking a Systems Engineer to work alongside the Manager of IT Infrastructure and support the day-to-day operation, reliability, and security of the company’s hybrid infrastructure. This role helps maintain the systems and technologies that employees rely on to work effectively and that WIN relies on to protect company and patient information.

The Systems Engineer will support on-premises and cloud environments, business continuity and disaster recovery capabilities, endpoint and server security, backups, and escalated technical issues. Occasional after-hours and weekend work is expected for scheduled maintenance, upgrades, project deadlines, system outages, and critical updates.

What You’ll Accomplish

· Ensure the functionality, availability, and performance of WIN’s hybrid IT infrastructure.

o Administer and maintain VMware 8.0 Enterprise, Dell servers, storage, switches, Palo Alto firewalls, and the zero-trust network environment.

o Manage certificates for internet-facing websites, servers, and appliances.

o Administer Active Directory, DHCP, DNS, Group Policy, Azure, and Entra ID.

o Support the Microsoft technology ecosystem, including Microsoft 365, OneDrive, SharePoint, and Intune.

o Maintain WIN’s Mimecast email security appliance and Omnissa Horizon VDI environment, including configuration and deployment.

o Support encryption for files, disks, email, and devices to help protect company and patient information in accordance with HIPAA requirements.

· Administer endpoint security, patch management, server software, and operating system deployments.

· Maintain connectivity to WIN’s primary data center and co-location environment in support of business continuity, disaster recovery, and incident response.

· Maintain WIN’s on-premises and cloud backup environments.

· Serve as an escalation point for complex IT Help Desk technical issues.

· Research technical issues and products, recommend practical solutions, and communicate clearly with technical and nontechnical partners.

What Success Looks Like

Success in this role means WIN’s infrastructure is reliable, secure, and well maintained; scheduled upgrades and maintenance are completed with minimal disruption; backups and business continuity systems are dependable; critical issues are addressed accurately and promptly; and technical solutions support the company’s operational needs.

Who You Are

· Reliable and accurate. You work carefully and consistently, especially when systems are under pressure.

· Analytical and solutions oriented. You investigate issues thoroughly, identify root causes, and develop practical technical solutions.

· Self-directed and organized. You prioritize competing needs, follow through on commitments, and manage work with close attention to detail.

· Clear and collaborative. You communicate effectively in writing and conversation and work well in a team-oriented environment.

· Curious and resourceful. You research unfamiliar issues and products and continue learning as technologies and business needs evolve.

· Business-minded. You evaluate technical options with operational impact and measurable return on investment in mind

Preferred Experience

· Bachelor’s degree in computer science or a related field is preferred.

· At least 5 years of relevant systems engineering or infrastructure experience.

· At least 5 years of experience deploying and maintaining Microsoft Windows Server and SQL Server environments.

· Working knowledge of Active Directory, DNS, DHCP, DFS, and Group Policy.

· Experience with computer networking and an understanding of routing and switching, including high-availability and redundancy features.

· Experience supporting hybrid infrastructure, Microsoft cloud services, virtualization, endpoint security, patch management, backups, and disaster recovery is preferred.

· U.S. work authorization is required.

Why You’ll Love Working at WIN

· Make a meaningful impact. Help improve the lives of individuals and families at every stage of life.

· Shape what's next. Join a growing company where your ideas can influence products, experiences, and the future of family well-being.

· Collaborate with purpose. Work alongside passionate teammates who care deeply about our mission and each other.

· Grow your career. Take on meaningful challenges, build new skills, and make a lasting impact in a fast-moving environment.

Benefits that Support Every Stage of Life

We offer a comprehensive benefits package designed to support the health, well-being, and financial security of our employees and their families, including:

· Medical, dental and vision coverage for full-time employees

· Family building and well being benefits

· 401 (k) retirement plan with Safe Harbor Match

· Life and disability insurance

· Generous Paid Time Off (PTO)

· Additional voluntary and supplemental benefits

Wage Range

The wage range for this position is $103,000 to $125,000. Wages will vary based on experience level, skill set, geography and other factors when determining wage levels.

Equal Opportunity Employer

WIN is an Equal Opportunity Employer. We are committed to providing equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, pregnancy, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, genetic information, or any other status protected by applicable federal, state, or local law.