Webster Bank · 4 days ago
Director, Enterprise Sales
Milwaukee, WI
Full-time
Hybrid
Mid, Senior Level
$150K/yr - $170K/yr
5+ years expWebster Bank is a leading commercial bank founded in 1935, focused on helping individuals, families, and businesses achieve their financial goals. The Enterprise Sales Executive will use a consultative sales approach to target large employers, leveraging HSA Bank’s resources to sell health-related benefit solutions while managing the full sales cycle.
Banking
Hiring Manager
Bridgette Yang
Responsibilities
Managing the full sales cycle—from prospecting to closing—with employers, national consultant firms, medical carriers, third-party administrators, and other key influencers within each account
Consistent track record in meeting and exceeding sales quotas of $1,000,000 in new sales revenue
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
Experience in cultivating relationships with existing accounts at the highest strategic level for additional sales
Knowledge of Health Savings Accounts, Consumer Driven Health Care, Group/Individual Health Insurance sales
Exceptional verbal and written skills
Up to 50% travel across multiple states
Qualification
Required
Bachelor's Degree required
Consistent track record in meeting and exceeding sales quotas of $1,000,000 in new sales revenue
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
Experience in cultivating relationships with existing accounts at the highest strategic level for additional sales
Knowledge of Health Savings Accounts, Consumer Driven Health Care, Group/Individual Health Insurance sales
Exceptional verbal and written skills
Up to 50% travel across multiple states
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
Preferred
Advanced degrees preferred
Previous experience working in a high growth financial industry is preferred
Benefits
Incentive compensation
Company
Webster Bank
Webster is a commercial bank that provides financial services to corporations, individuals, families, and partners.
1001-5000 employees
Funding
Current Stage
Public CompanyTotal Funding
$653MKey Investors
Greystone
2025-09-11Post Ipo Debt· $350M
2024-12-02Post Ipo Debt· $303M
2002-10-17IPO
Leadership Team
Neal Holland
Chief Financial Officer
D
Daniel Gioia
Sr. Managing Director
Recent News
Providence Business News
2026-01-16
Hartford Business Journal
2025-11-06
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