Join Our Team

Join Our Team

Join Our Team

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!

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 150 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 intent on 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.

Perks at FIRST

Business casual dress code

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

Potential to work remotely

Ongoing learning and development, including individual development plans

Balanced work-life philosophy

Team-building events and activities

Celebrations, parties, annual company events, and sport leagues

Health and wellness events such as yoga classes, chair massages, and on-site flu shots

Stand-up work stations and treadmill desks

Committees for green initiativesdiversity and inclusion, and employee engagement

Community service opportunities

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.