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Director, Mid-Market Sales Representative

HSA Bank, a division of Webster Bank, N.A.
Green, WI Full Time
POSTED ON 4/17/2026
AVAILABLE BEFORE 5/16/2026
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?

Employs a consultative based sales approach to identify, pursue, and achieve sales goals and quota of new employer accounts in the assigned sales territory. The RVP will leverage the internal assets of HSA Bank to sell health-based accounts including Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs) and Commuter Benefits (Mass Transit & Parking) and COBRA to employers with 1,500 to 9,999 employees.

What You Will Do

  • Employs a consultative based sales approach to identify, pursue, and achieve sales goals and quota of new employer accounts in the assigned sales territory.
  • Leverage the internal assets of HSA Bank to sell health-based accounts including Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs), Health Reimbursement Arrangements (HRAs) and Commuter Benefits (Mass Transit & Parking) and COBRA to employers with 1,500 to 9,999 employees.
  • Manage the sales process while selling to Employers directly, Insurance Consultants, Broker, Carriers, Investment Advisors, TPAs, as well as key influencers within each account.

Skills And Abilities

  • Knowledge of Health Savings Accounts, Consumer Driven Health Care, Group/Individual Health Insurance sales, Managed Healthcare and the Agent/Broker distribution system.
  • Exceptional verbal and written skills.
  • Consistent track record in meeting and exceeding sales quotas.
  • Proven experience in proactively identifying and closing new account opportunities in an assigned territory.
  • Ability to manage sales through forecasting, account resource allocation, account strategy and ecosystem partnerships.

Education Qualifications

  • H.S. Diploma or General Education Degree (GED) required
  • Candidates with advanced degrees (Associates, Bachelor's, and/or Master's) preferred

Experience Qualifications

  • 8-9 years experience in cultivating relationships with existing accounts at the highest strategic level for additional sales required

The estimated salary range for this position is $130,000USD to $140,000USD. 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 : $140,000

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