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Regional Vice President, Sales

HSA Bank, a division of Webster Bank, N.A.
Milwaukee, WI Full Time
POSTED ON 2/6/2026 CLOSED ON 4/5/2026

What are the responsibilities and job description for the Regional Vice President, Sales position at HSA Bank, a division of Webster Bank, N.A.?

At HSA Bank, we’re working toward a world where everyone is empowered to save for a healthy future. Our offerings in the healthcare savings space drive down healthcare costs, increase access, and assist with decision-making for consumers, health plans, partners, and advisors.

Are you ready to join us?

Job Summary

We are seeking a proven sales leader with deep experience in employee benefits solutions to join our team as a Regional Vice President (RVP), Sales. This role focuses on driving growth through a consultative sales approach, targeting new employer accounts within the assigned territory. The RVP will manage the sales process while selling to Employers directly, Health & Welfare Consultants, Brokers, Third-Party Partnerships, as well as key influencers within each account.

The ideal candidate will have a strong track record of selling employee benefits programs and working closely with consultants to deliver strategic solutions to mid-market employers (1,500–10,000 employees). Experience with products such as Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs), Commuter Benefits, and COBRA is highly preferred, but not required. This is a fully remote position, but candidates ideally reside in Ohio, Michigan, or Tennessee to best serve the region.

Key Qualifications And Responsibilities Include

  • Proven history of consistently meeting and surpassing sales targets.
  • Strong ability to work independently, proactively identify opportunities, and close new accounts within assigned territories.
  • Skilled in managing sales through accurate forecasting, strategic account planning, resource allocation, and leveraging ecosystem partnerships.
  • Experienced in collaborating with Employee Benefit brokers and consultants.
  • In-depth knowledge of Health Savings Accounts (HSAs), Consumer-Driven Health Care, Group and Individual Health Insurance sales, Managed Healthcare, and the Agent/Broker distribution system.
  • Excellent verbal and written communication skills.
  • Willingness to travel up to 30% across multiple states.

Qualifications

  • Bachelor's Degree required
  • Minimum of five (5) years of sales experience in Employee Benefits, Asset Management, or Benefits Consulting
  • Salesforce or other CRM tool skills
  • Excellent presentation and communication skills
  • Previous experience working in a high growth healthcare/financial industry is preferred

The estimated salary range for this position is $135,000USD to $145,000USD. Actual salary may vary up or down depending on job-related factors which may include knowledge, skills, experience, and location. In addition, this position is eligible for incentive compensation.

Webster Financial Corporation and its subsidiaries (“Webster”) are equal opportunity employers that are committed to sustaining an inclusive environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, marital status, national origin, ancestry, citizenship, sex, sexual orientation, gender identity and/or expression, physical or mental disability, protected veteran status, or any other characteristic protected by law.

Salary : $135,000 - $145,000

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