About The Position

At Associated Bank we strive to create an inclusive culture where different perspectives are valued and recognized as strengths critical to our success. If you thrive in an environment where your growth and development are encouraged and supported, then Associated Bank may be the right place for you. Associated Bank requires you to directly represent yourself and your own experiences during the recruiting and hiring process. Associated Bank conducts a thorough background check on all new hires. The Health Savings Account Program and Systems Lead ensures the systems, applications, and portals supporting Associated Bank’s HSA offerings are reliable, scalable, and aligned to business goals. This role partners across business, technology, and vendors to support product launches, system enhancements, and ongoing operations. You’ll have the opportunity to influence strategy, improve processes, and drive meaningful improvements to the HSA experience. Key Accountabilities Support HSA strategic initiatives and product launches by ensuring systems are ready and aligned with business objectives. Lead system testing and validation activities, including UAT, post-release checks, and disaster recovery exercises. Maintain lower and demo environments to support testing, training, and onboarding. Partner with business teams, IT, vendors, and third parties to deliver system upgrades and enhancements. Resolve complex system issues by providing Level 2 support and managing issues through resolution. Coordinate portal updates, user access, and content changes across internal and external platforms. Develop and maintain clear, accurate system documentation and process controls. Education & Experience Required Bachelor’s degree or equivalent combination of education and experience 6+ years experience supporting systems, applications, or operations in financial services, benefits administration, or healthcare accounts 3+ years experience in system testing, configuration, and release management 3+ years experience working cross-functionally with business, technology, and vendors 3+ years experience analyzing technical or process issues and communicating solutions effectively Preferred Experience supporting HSA, FSA, or benefits administration platforms Familiarity with vendor-supported systems and third-party integrations Experience with portals, CRM tools, or benefits administration platforms Why You’ll Love Working Here At Associated Bank, you’ll join a collaborative, purpose-driven team that values innovation, accountability, and continuous improvement. We invest in your growth through meaningful work, professional development, and opportunities to influence strategy. Apply today to make an impact. We welcome and encourage applications from individuals returning to the workforce, people with disabilities, candidates without a college degree, and veterans or those with military experience. In addition to core traditional benefits, we take pride in offering benefits for every stage of life. Retirement savings including both 401(k) and Pension plans. Paid time off to volunteer in your community. Opportunities to connect with others through our diversity-focused Colleague Resource Groups. Competitive salaries with professional development and advancement opportunities. Bonus benefits including well-being programs and incentives, parental leave, an employee stock purchase plan, military benefits and much more. Personal banking, loan, investment and insurance benefits. Associated Bank serves more than 120 communities throughout Wisconsin, Illinois, Minnesota, and Missouri and we consider our colleagues critical to our continued success. See why our colleagues continually vote us a best place to work in the Midwest. Join our community on Facebook, LinkedIn and X. Compliance Statement Associated Bank is an equal opportunity employer committed to creating a diverse workforce. We support a work environment where colleagues are respected and given the opportunity to perform to their fullest potential. We consider all qualified applicants without regard to race, religion, color, sex, national origin, age, sexual orientation, gender identity, disability or veteran status, among other factors. Fully complies with all applicable enterprise policies and procedures. Acts in compliance with all applicable laws and regulations as outlined in training materials, including but not limited to Bank Secrecy Act. Responsible for reporting suspicious activity to Financial Intelligence. Responsible to report all customer complaints as prescribed and procedure violations to management or HR. Responsible to report ethical concerns as needed to Associated Bank’s anonymous Ethics Hotline. Associated Bank provides additional assistance throughout the application, interview and hiring process. Please contact [email protected] if you need an accommodation at any time during the process. Associated Banc-Corp participates in the E-Verify Program. E-Verify Notice English or Spanish. Know Your Right to Work English or Spanish. Associated Bank is Pay Transparency compliant. The pay range represents anticipated base pay for this role. Actual pay may vary based on factors including, but not limited to, work location, skills, experience, education, and qualifications for the role. $71,540.00 - $122,640.00 per year At Associated Bank, our purpose is to uplift our customers, community and colleagues to be financially stronger. We do this through our relentless focus on people, with a winning spirit, by listening before we act and with a commitment to achieve together. What does it mean to be #RootedHere? For us, it means having a career that grows with you. We think you'll like the opportunities available at Associated Bank. Introduce yourself to our talent acquisition consultants and we'll contact you if there's a role that seems like a good match.

Requirements

  • Bachelor’s degree or equivalent combination of education and experience
  • 6+ years experience supporting systems, applications, or operations in financial services, benefits administration, or healthcare accounts
  • 3+ years experience in system testing, configuration, and release management
  • 3+ years experience working cross-functionally with business, technology, and vendors
  • 3+ years experience analyzing technical or process issues and communicating solutions effectively

Nice To Haves

  • Experience supporting HSA, FSA, or benefits administration platforms
  • Familiarity with vendor-supported systems and third-party integrations
  • Experience with portals, CRM tools, or benefits administration platforms

Responsibilities

  • Support HSA strategic initiatives and product launches by ensuring systems are ready and aligned with business objectives.
  • Lead system testing and validation activities, including UAT, post-release checks, and disaster recovery exercises.
  • Maintain lower and demo environments to support testing, training, and onboarding.
  • Partner with business teams, IT, vendors, and third parties to deliver system upgrades and enhancements.
  • Resolve complex system issues by providing Level 2 support and managing issues through resolution.
  • Coordinate portal updates, user access, and content changes across internal and external platforms.
  • Develop and maintain clear, accurate system documentation and process controls.

Benefits

  • Retirement savings including both 401(k) and Pension plans.
  • Paid time off to volunteer in your community.
  • Opportunities to connect with others through our diversity-focused Colleague Resource Groups.
  • Competitive salaries with professional development and advancement opportunities.
  • Bonus benefits including well-being programs and incentives, parental leave, an employee stock purchase plan, military benefits and much more.
  • Personal banking, loan, investment and insurance benefits.
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