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Join Our Team

We are always on the lookout for talented and engaged team members who want to join a workplace environment that fosters success.

FIRST Insurance Funding, a division of Wintrust, prides itself on its commitment to service. Not only do we provide excellent service to our clients but to our coworkers, as well. With management’s open door policy, every employee has a voice. Everyone helps FIRST to continually improve processes and maintain open lines of communication.

We offer an engaging, dynamic work environment and an excellent compensation package, including 401(k), employee stock purchase plan, medical/dental, life insurance, and more!

See Our Mission, Vision, and Values

Open Positions

People-Centric to The Core

It is important to have a genuine connection to the work you do. At Wintrust, doing business differently and delivering better results for our customers starts with valuing you as a person, first.

Community Matters

Our commitment to our customers and communities runs deep. We believe in improving lives, giving back, and achieving great results in the communities we call home.

Work, But make it Fun

We know that a collaborative work culture fosters creativity and innovation. We are serious about rising to challenges, being accountable, and keeping work fun. 

Driven to Make a Difference

At the core, our purpose is people. Because it feels good to do good every day.

Diverse and Inclusive, by Design

We are committed to creating an inclusive workplace where everyone feels welcome and valued.

Perks at FIRST

Business casual dress code
 

Flexible work schedule between
7 a.m. and 7 p.m. CST
 

Ongoing learning and development, including individual development plans
 

Balanced work-life philosophy
 

Team-building events and activities
 

Celebrations, parties, annual company events, and sports leagues
 

Health and wellness
 

Committees for green initiatives, diversity and inclusion, and employee engagement
 

Community service opportunities

About Wintrust

In 1991, we opened one storefront community bank location with one specific goal: to provide an alternative to the big banks that were just beginning to flood the market. We believed — and still do — that people deserve a warm, friendly, honest, and highly responsive banking experience.

 Today, we’re proud to be Chicago’s Bank® and Wisconsin’s Bank®. We’ve also grown into a company with a presence across the U.S. and Canada. We have more than 170 community banks and provide a variety of offerings, including commercial banking, premium financing, mortgage origination, wealth management, and short-term accounts receivable financing, just to name a few. Every bank and group that has joined the Wintrust family along the way has stayed true to that original mission, thanks to our employees who serve as brand champions and live our values.

Entrepreneurial, customer-focused, and team-oriented people thrive here at Wintrust. We approach each day with the intent of making an impact and believe in providing truly distinctive customer service. We’re not just in the communities we serve. We’re part of them.

Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, ethnicity, gender, sexual orientation, gender identity, national origin, veteran status, or disability.

Residential lending provided by Wintrust Mortgage, a division of Barrington Bank & Trust Company, N.A., a Wintrust Community Bank, NMLS #449042.

Securities, insurance products, financial planning, & investment management services offered through Wintrust Investments, LLC (Member FINRA/SIPC), founded in 1931. Asset management & financial planning services offered by Great Lakes Advisors. Trust services provided by The Chicago Trust Company, N.A.

Investment products such as stocks, bonds, & mutual funds are:
NOT FDIC INSURED | NOT BANK GUARANTEED | MAY LOSE VALUE | NOT A DEPOSIT | NOT INSURED BY ANY FEDERAL GOVERNMENT AGENCY