Director, Mid-Market Sales

Webster Bank

Director, Sales at HSA Bank employing consultative sales in health savings accounts to employers. Aiming for sales goals in a territory involving 1,500 to 9,999 employee accounts.

Posted 4/16/2026full-timeRemote • California, Wisconsin • 🇺🇸 United StatesLead💰 $130,000 - $140,000 per yearWebsite

About the role

Key responsibilities & impact

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

Requirements

What you’ll need

8-9 years experience in cultivating relationships with existing accounts at the highest strategic level for additional sales required
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
H.S. Diploma or General Education Degree (GED) required
Candidates with advanced degrees (Associates, Bachelor's, and/or Master's) preferred

Benefits

Comp & perks

Eligible for incentive compensation

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Health Savings AccountsFlexible Spending AccountsHealth Reimbursement ArrangementsCommuter BenefitsCOBRAGroup Health Insurance salesIndividual Health Insurance salesManaged HealthcareSales forecastingAccount resource allocation

Soft Skills

consultative sales approachrelationship cultivationverbal communicationwritten communicationsales quota achievementproactive account managementstrategic account planningecosystem partnership management

Certifications

H.S. DiplomaGeneral Education Degree (GED)Associates degreeBachelor's degreeMaster's degree