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Director, Enterprise Sales
full-timeColorado, Boulder, Nevada, Milwaukee, Arizona$150k - $170k

Summary

Location

Colorado, Boulder, Nevada, Milwaukee, Arizona

Salary

$150k - $170k

Type

full-time

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About this role

If you’re looking for a meaningful career, you’ll find it here at Webster. Founded in 1935, our focus has always been to put people first--doing whatever we can to help individuals, families, businesses and our colleagues achieve their financial goals. As a leading commercial bank, we remain passionate about serving our clients and supporting our communities. Integrity, Collaboration, Accountability, Agility, Respect, Excellence are Webster’s values, these set us apart as a bank and as an employer.  

Come join our team where you can expand your career potential, benefit from our robust development opportunities, and enjoy meaningful work!

The Enterprise Sales Executive (ESE) uses a consultative sales approach to identify, pursue, and achieve sales goals targeting employers with more than 10,000 U.S. based employees located within a defined territory that includes the key states of CA, WA, CO, UT, OR, TX.

This is a home-based position located in the Western U.S. The ESE will leverage HSA Bank’s resources to sell health-related benefit solutions, including:

Health Savings Accounts (HSAs)
Flexible Spending Accounts (FSAs)
Health Reimbursement Arrangements (HRAs)
Commuter Benefits (Mass Transit & Parking)
Lifestyle Spending and Emergency Savings Accounts
Responsibilities include 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.

Job Summary:

The Enterprise Sales Executive (ESE) uses a consultative sales approach to identify, pursue, and achieve sales goals targeting employers with more than 10,000 U.S. based employees located within a defined territory that includes the key states of CA, WA, CO, UT, OR, TX.

This is a home-based position located in the Western U.S. The ESE will leverage HSA Bank’s resources to sell health-related benefit solutions, including:

  • Health Savings Accounts (HSAs)

  • Flexible Spending Accounts (FSAs)

  • Health Reimbursement Arrangements (HRAs)

  • Commuter Benefits (Mass Transit & Parking)

  • Lifestyle Spending and Emergency Savings Accounts

Responsibilities include 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.

Ideally looking for candidates to reside in the state of California, Washington, Arizona, or Texas

Key qualifications and responsibilities include:

  • 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

Qualifications:

  • Bachelor's Degree required; Advanced degrees preferred

  • 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 financial industry is preferred

The estimated salary range for this position is $150,000USD to $170,000USD. 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.

#LI-BY1

#LI-REMOTE

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.

Other facts

Tech stack
Sales,Consultative Sales,Account Management,Relationship Building,Health Savings Accounts,Flexible Spending Accounts,Health Reimbursement Arrangements,Commuter Benefits,Lifestyle Spending,Emergency Savings Accounts,Forecasting,Account Strategy,Communication,Presentation Skills,CRM Tools,Employee Benefits

About Webster Bank

Webster Bank (NYSE:WBS*) is a values-based, leading commercial bank with more than $81.9 billion in assets focused on delivering financial solutions to businesses, individuals and families. With headquarters in Stamford, Connecticut, our footprint spans the Northeast from the New York City metropolitan area to Rhode Island and Massachusetts.

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.

© 2025 Webster Financial Corporation. All rights reserved.
Webster Bank, the Webster Bank logo and the W symbol are trademarks of Webster Financial Corporation and Registered in the U.S. Patent and Trademark Office.

Team size: 1,001-5,000 employees
LinkedIn: Visit
Industry: Banking
Founding Year: 1935

What you'll do

  • The Enterprise Sales Executive manages the full sales cycle from prospecting to closing with employers and key influencers. They will target employers with over 10,000 U.S. based employees within a defined territory.

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Frequently Asked Questions

What does Webster Bank pay for a Director, Enterprise Sales?

Webster Bank offers a competitive compensation package for the Director, Enterprise Sales role. The salary range is USD 150k - 170k per year. Apply through Clera to learn more about the full compensation details.

What does a Director, Enterprise Sales do at Webster Bank?

As a Director, Enterprise Sales at Webster Bank, you will: the Enterprise Sales Executive manages the full sales cycle from prospecting to closing with employers and key influencers. They will target employers with over 10,000 U.S. based employees within a defined territory..

Why join Webster Bank as a Director, Enterprise Sales?

Webster Bank is a leading Banking company. The Director, Enterprise Sales role offers competitive compensation.

Is the Director, Enterprise Sales position at Webster Bank remote?

The Director, Enterprise Sales position at Webster Bank is based in Colorado, United States and Boulder, Utah, United States. Contact the company through Clera for specific work arrangement details.

How do I apply for the Director, Enterprise Sales position at Webster Bank?

You can apply for the Director, Enterprise Sales position at Webster Bank directly through Clera. Click the "Apply Now" button above to start your application. Clera's AI-powered platform will help match your profile with this opportunity and guide you through the application process. You can also learn more about Webster Bank on their website.