TECHNICAL SUPPORT 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, were transforming how people access care during lifes most meaningful moments. For nearly 30 years, weve 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-beingand we're looking for teammates who are excited to help shape what's next. The Opportunity WIN is seeking a Technical Support Engineer to provide comprehensive technical support across the organization and serve as a key contributor to a reliable, secure, and high-performing technology environment. Working under the guidance of the Technical Support Team Lead or Manager, this role supports the full employee technology lifecycle, from onboarding and device deployment through offboarding and asset recovery. The Technical Support Engineer is responsible for resolving technical issues in a timely and professional manner, maintaining accurate documentation within WIN's Help Desk ticketing system, and supporting critical infrastructure and end-user technologies. This position works closely with internal technology teams, business stakeholders, external vendors, and development partners to ensure employees have the tools and support they need to work effectively. The role also participates in after-hours support and scheduled maintenance activities when needed. What Youll Accomplish Serve as first-line technical support for both onsite and remote employees, providing prompt, professional assistance in a secure and compliance-focused environment. Provide end-to-end support for employee technology needs, including onboarding, offboarding, installation, configuration, troubleshooting, and maintenance of devices and systems. Install, configure, support, and troubleshoot servers, workstations, laptops, mobile devices, operating systems, and business applications. Perform hardware and software upgrades to maintain optimal system performance and user productivity. Configure, test, deploy, and maintain operating systems and application software environments. Administer and support enterprise technologies including Active Directory, Microsoft Exchange, VMware, endpoint management tools, Mitel phone systems, and network printers. Diagnose and resolve issues involving networking equipment, business applications, hardware devices, and peripherals. Collaborate with infrastructure teams, database administrators, project managers, system integration teams, and onsite and offshore development teams to support technology initiatives and issue resolution. Partner with external vendors to procure, support, and maintain hardware, software, communications systems, and related IT services. Participate in the evaluation, recommendation, planning, and implementation of new hardware, software, and technology upgrades. Maintain accurate documentation of support requests, troubleshooting steps, and resolutions within WIN's Help Desk ticketing system. Provide after-hours support and participate in scheduled maintenance activities outside standard business hours as needed. What Success Looks Like Success in this role means employees receive timely, professional, and effective technical support; support tickets are accurately documented and resolved within expected timeframes; devices and systems are deployed and maintained reliably; onboarding and offboarding processes run smoothly; and technology issues are resolved with minimal disruption to business operations. The Technical Support Engineer contributes to a positive employee experience by ensuring users have secure, dependable access to the technology they need while helping maintain WIN's infrastructure, security, and operational efficiency. 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 Information Technology, Computer Science, or a related field; or an Associate degree combined with relevant certifications and equivalent experience. Minimum of 2 years of hands-on experience supporting end users, troubleshooting networks, and working in a Help Desk or technical support environment. Experience deploying, administering, and supporting Windows 10 environments, Microsoft Office applications, and Windows Server platforms including 2008, 2012, 2016, and 2019. Experience supporting desktop and network hardware, operating systems, mobile devices, and peripheral equipment. Knowledge of TCP/IP networking, DHCP, DNS, Active Directory, DFS, Group Policy Objects (GPOs), VMware environments, SAN systems, and data security best practices. Experience supporting enterprise collaboration, endpoint management, telecommunications, and infrastructure technologies is preferred. Why Youll 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 $60,000 to $65,000. 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.