Financial Representative Trainee (Sales)--Milwaukee, WILocation: WisconsinWork Type: Full Time RegularJob No: 503419Categories: Sales, Early Career Programs, Financial Representative TraineeApplication Closes: Open Until Filled SHARE Are you driven, self-motivated, and eager to jumpstart your career in the financial services industry We’re seeking passionate individuals to join our Accelerator Program, a dynamic trainee experience designed to set you up for long-term success. As a Financial Representative Trainee, you’ll embark on a comprehensive program that equips you with the skills and competencies necessary to excel in selling Individual Insurance products and building a sustainable, holistic financial practice. Through a combination of self-study, hands-on projects, and experienced mentorship, you’ll receive the training and support you need to run your own business and build a rewarding career.WHAT WE CAN OFFER YOU:Hourly Wage: $16/hour during the trainee period, which lasts up to 30 days.Upon completion of the trainee period, promotion to a Financial Representative with a $36,000 annual base plus unlimited monthly sales incentive.$1000 bonus after successful completion of trainee period and promotion to a Financial Representative.An education-based Accelerator Program designed to successfully transition you to an independent Financial Advisor.Benefits and Perks, 401(k) plan with a 2% company contribution and 6% company match.Regular associates working 40 hours a week can earn up to 15 days of vacation each year.Regular associates receive 11 paid holidays in 2025, which includes 2 floating holidays that are added to your prorated personal time to be used at your discretion.Regular associates are provided sick leave through the use of personal time. Associates working 40 hours a week can receive up to 40 hours of personal time in 2025, which is prorated based on the start date.Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.WHAT YOU'LL DO:You’ll participate in a comprehensive program to develop the skills required to provide holistic financial advice to clients. You will actively contribute to classroom discussion, participate in goal setting sessions and progress evaluation meetings.You’ll gain valuable direct sales experience in marketing Individual Insurance products to clients and pass a sales process competency test.You’ll cultivate and sustain prospecting skills such as research, targeting, networking, communication and more through use of personal networks, community events, and social media.You’ll acquire an in-depth understanding of our product offerings, demonstrating expertise in their features and benefits.You’ll oversee completion of content, proposals and paperwork flow throughout the field and Home Office, ensuring a seamless application and underwriting process.WHAT YOU’LL BRING:Successfully meet all trainee program requirements, gaining the skills and knowledge needed to excel.Obtain the required insurance licenses prior to starting the job, with up to two attempts allowed for the Life and Health exam.Pass the CRD/FINRA background check at hire and ongoing, with securities licensing required within 24 months of entry into the program.Be highly self-motivated and results-oriented, working both independently and as part of a team.Be able to travel up to 50% of the time, hold and maintain a valid U.S. driver's license, and have access to reliable transportation for meetings and appointments.You promote a culture of diversity and inclusion, value different ideas and opinions, and listen courageously, remaining curious in all that you do.PREFERRED:Knowledge of the Insurance/Financial Services industry, products and marketing practices.Bachelor's degree or equivalent preferred but not required.We value diverse experience, skills, and passion for innovation. If your experience aligns with the listed requirements, please apply!After applying, for inquiries about your application or the hiring process please email our Talent Acquisition area at . Need help Email UsApply Now Great place to workTogether we achieve greatness. Not only is this a core value, but it’s also representative of the kind of place we are built by the strength and integrity of our employees. It’s why we’re named a “Great Place to Work”.See All AwardsAn inclusive cultureSurround yourself with an authentic and inclusive culture. Your strengths and differences will be valued and celebrated by a diverse community of co-workers.Discover Our Culture Related Job OpeningsFinancial Business Consultant - Remote Remote | 503598 Financial Representative Trainee (Sales) - Des Moines, IA Iowa | 503425 Renewal Executive - Nashville, TN Tennessee | 503588

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join us as a full-time Teller Supervisor! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: The Teller Supervisor is responsible for the supervision of teller staff and all branch functions associated with processing customer transactions and providing routine banking services. This position requires strong leadership, organizational, and communication skills to motivate staff and effectively organize and delegate duties among the teller staff. Responsibilities include:Operate a teller drawer to serve customers in lobby or drive upRecognize potential cross-sell opportunities and direct customers to appropriate bank personnelTake a proactive approach to solving operational issues and make approvals/exceptions to policy as neededRecognize and report potential fraud to management. Ensure compliance of all department, bank and regulatory policies and procedures are followed to maintain safety of customers and employeesPerform routine monthly audits and daily/monthly sales trackingParticipates in hiring, onboarding, training and ongoing development of teller staff including performance reviewsUphold established Wintrust culture by providing best-in-class customer service and participating in community eventsQualifications:Previous teller experience required3-5 years of supervisory experience preferred, preferably within a financial institutionExcellent customer service and communication skillsHigh school diploma or equivalentTravel between branches may be necessaryAbility to lift 30 lbsAbility to stand for long periods of timeBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimatedhourly ratefor this role is $21.00-24.00, along with eligibility to earn an annual bonus. Actualpayrate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Financial Representative Trainee (Sales)--Milwaukee, WILocation: WisconsinWork Type: Full Time RegularJob No: 503419Categories: Sales, Early Career Programs, Financial Representative TraineeApplication Closes: Open Until Filled SHARE Are you driven, self-motivated, and eager to jumpstart your career in the financial services industry We’re seeking passionate individuals to join our Accelerator Program, a dynamic trainee experience designed to set you up for long-term success. As a Financial Representative Trainee, you’ll embark on a comprehensive program that equips you with the skills and competencies necessary to excel in selling Individual Insurance products and building a sustainable, holistic financial practice. Through a combination of self-study, hands-on projects, and experienced mentorship, you’ll receive the training and support you need to run your own business and build a rewarding career.WHAT WE CAN OFFER YOU:Hourly Wage: $16/hour during the trainee period, which lasts up to 30 days.Upon completion of the trainee period, promotion to a Financial Representative with a $36,000 annual base plus unlimited monthly sales incentive.$1000 bonus after successful completion of trainee period and promotion to a Financial Representative.An education-based Accelerator Program designed to successfully transition you to an independent Financial Advisor.Benefits and Perks, 401(k) plan with a 2% company contribution and 6% company match.Regular associates working 40 hours a week can earn up to 15 days of vacation each year.Regular associates receive 11 paid holidays in 2025, which includes 2 floating holidays that are added to your prorated personal time to be used at your discretion.Regular associates are provided sick leave through the use of personal time. Associates working 40 hours a week can receive up to 40 hours of personal time in 2025, which is prorated based on the start date.Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.WHAT YOU'LL DO:You’ll participate in a comprehensive program to develop the skills required to provide holistic financial advice to clients. You will actively contribute to classroom discussion, participate in goal setting sessions and progress evaluation meetings.You’ll gain valuable direct sales experience in marketing Individual Insurance products to clients and pass a sales process competency test.You’ll cultivate and sustain prospecting skills such as research, targeting, networking, communication and more through use of personal networks, community events, and social media.You’ll acquire an in-depth understanding of our product offerings, demonstrating expertise in their features and benefits.You’ll oversee completion of content, proposals and paperwork flow throughout the field and Home Office, ensuring a seamless application and underwriting process.WHAT YOU’LL BRING:Successfully meet all trainee program requirements, gaining the skills and knowledge needed to excel.Obtain the required insurance licenses prior to starting the job, with up to two attempts allowed for the Life and Health exam.Pass the CRD/FINRA background check at hire and ongoing, with securities licensing required within 24 months of entry into the program.Be highly self-motivated and results-oriented, working both independently and as part of a team.Be able to travel up to 50% of the time, hold and maintain a valid U.S. driver's license, and have access to reliable transportation for meetings and appointments.You promote a culture of diversity and inclusion, value different ideas and opinions, and listen courageously, remaining curious in all that you do.PREFERRED:Knowledge of the Insurance/Financial Services industry, products and marketing practices.Bachelor's degree or equivalent preferred but not required.We value diverse experience, skills, and passion for innovation. If your experience aligns with the listed requirements, please apply!After applying, for inquiries about your application or the hiring process please email our Talent Acquisition area at . Need help Email UsApply Now Great place to workTogether we achieve greatness. Not only is this a core value, but it’s also representative of the kind of place we are built by the strength and integrity of our employees. It’s why we’re named a “Great Place to Work”.See All AwardsAn inclusive cultureSurround yourself with an authentic and inclusive culture. Your strengths and differences will be valued and celebrated by a diverse community of co-workers.Discover Our Culture Related Job OpeningsFinancial Business Consultant - Remote Remote | 503598 Financial Representative Trainee (Sales) - Des Moines, IA Iowa | 503425 Renewal Executive - Nashville, TN Tennessee | 503588

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Chicago’s Bank®, as a full-time Relationship Banker! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: As a Relationship Banker, you will build and retain meaningful relationships with your customers, using your financial knowledge to recommend thoughtful solutions to meet their needs. In this dual role, you will contribute to the success of the branch by:Building lasting relationships with customers, discovering their financial needs and tailoring product and service recommendationsCollaborating with business partners (Mortgage, Wealth Management) to connect customers to experts who can help with specialized needsOperating a teller drawer serving customers in the lobby/drive-upOpening accounts, performing account maintenance and assisting customers with digital productsRecognizing potential fraud and other risksDepending on the shift, you might be responsible for bank opening/closingHelping support community and bank eventsQualifications:1-3 years of experience in a customer service, financial service, or sales roleHigh School Degree or equivalentIntermediate computer skillsBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimatedhourly ratefor this role is $21.00-$28.00, along with eligibility to earn monthly commissions. Actualpayrate may vary based on several factors, such as a candidate’s qualifications, skills and experience.#LI-MG1#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Financial Representative Trainee (Sales)--Milwaukee, WILocation: WisconsinWork Type: Full Time RegularJob No: 503419Categories: Sales, Early Career Programs, Financial Representative TraineeApplication Closes: Open Until Filled SHARE Are you driven, self-motivated, and eager to jumpstart your career in the financial services industry We’re seeking passionate individuals to join our Accelerator Program, a dynamic trainee experience designed to set you up for long-term success. As a Financial Representative Trainee, you’ll embark on a comprehensive program that equips you with the skills and competencies necessary to excel in selling Individual Insurance products and building a sustainable, holistic financial practice. Through a combination of self-study, hands-on projects, and experienced mentorship, you’ll receive the training and support you need to run your own business and build a rewarding career.WHAT WE CAN OFFER YOU:Hourly Wage: $16/hour during the trainee period, which lasts up to 30 days.Upon completion of the trainee period, promotion to a Financial Representative with a $36,000 annual base plus unlimited monthly sales incentive.$1000 bonus after successful completion of trainee period and promotion to a Financial Representative.An education-based Accelerator Program designed to successfully transition you to an independent Financial Advisor.Benefits and Perks, 401(k) plan with a 2% company contribution and 6% company match.Regular associates working 40 hours a week can earn up to 15 days of vacation each year.Regular associates receive 11 paid holidays in 2025, which includes 2 floating holidays that are added to your prorated personal time to be used at your discretion.Regular associates are provided sick leave through the use of personal time. Associates working 40 hours a week can receive up to 40 hours of personal time in 2025, which is prorated based on the start date.Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.WHAT YOU'LL DO:You’ll participate in a comprehensive program to develop the skills required to provide holistic financial advice to clients. You will actively contribute to classroom discussion, participate in goal setting sessions and progress evaluation meetings.You’ll gain valuable direct sales experience in marketing Individual Insurance products to clients and pass a sales process competency test.You’ll cultivate and sustain prospecting skills such as research, targeting, networking, communication and more through use of personal networks, community events, and social media.You’ll acquire an in-depth understanding of our product offerings, demonstrating expertise in their features and benefits.You’ll oversee completion of content, proposals and paperwork flow throughout the field and Home Office, ensuring a seamless application and underwriting process.WHAT YOU’LL BRING:Successfully meet all trainee program requirements, gaining the skills and knowledge needed to excel.Obtain the required insurance licenses prior to starting the job, with up to two attempts allowed for the Life and Health exam.Pass the CRD/FINRA background check at hire and ongoing, with securities licensing required within 24 months of entry into the program.Be highly self-motivated and results-oriented, working both independently and as part of a team.Be able to travel up to 50% of the time, hold and maintain a valid U.S. driver's license, and have access to reliable transportation for meetings and appointments.You promote a culture of diversity and inclusion, value different ideas and opinions, and listen courageously, remaining curious in all that you do.PREFERRED:Knowledge of the Insurance/Financial Services industry, products and marketing practices.Bachelor's degree or equivalent preferred but not required.We value diverse experience, skills, and passion for innovation. If your experience aligns with the listed requirements, please apply!After applying, for inquiries about your application or the hiring process please email our Talent Acquisition area at . Need help Email UsApply Now Great place to workTogether we achieve greatness. Not only is this a core value, but it’s also representative of the kind of place we are built by the strength and integrity of our employees. It’s why we’re named a “Great Place to Work”.See All AwardsAn inclusive cultureSurround yourself with an authentic and inclusive culture. Your strengths and differences will be valued and celebrated by a diverse community of co-workers.Discover Our Culture Related Job OpeningsFinancial Business Consultant - Remote Remote | 503598 Financial Representative Trainee (Sales) - Des Moines, IA Iowa | 503425 Renewal Executive - Nashville, TN Tennessee | 503588

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Chicago’s Bank®, as a full-time Relationship Banker! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 11 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: As a Relationship Banker, you will build and retain meaningful relationships with your customers, using your financial knowledge to recommend thoughtful solutions to meet their needs. In this dual role, you will contribute to the success of the branch by:Building lasting relationships with customers, discovering their financial needs and tailoring product and service recommendationsCollaborating with business partners (Mortgage, Wealth Management) to connect customers to experts who can help with specialized needsOperating a teller drawer serving customers in the lobby/drive-upOpening accounts, performing account maintenance, and assisting customers with digital productsRecognizing potential fraud and other risksDepending on the shift, you might be responsible for bank opening/closingHelping support community and bank eventsQualifications:1+ years teller experience (banker experience preferred)High School Degree or GEDIntermediate computer skillsBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation:The estimatedhourly ratefor this role is $21.00-$28.00. Actualpayrate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITE#LI-KP1From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Financial Representative Trainee (Sales)--Milwaukee, WILocation: WisconsinWork Type: Full Time RegularJob No: 503419Categories: Sales, Early Career Programs, Financial Representative TraineeApplication Closes: Open Until Filled SHARE Are you driven, self-motivated, and eager to jumpstart your career in the financial services industry We’re seeking passionate individuals to join our Accelerator Program, a dynamic trainee experience designed to set you up for long-term success. As a Financial Representative Trainee, you’ll embark on a comprehensive program that equips you with the skills and competencies necessary to excel in selling Individual Insurance products and building a sustainable, holistic financial practice. Through a combination of self-study, hands-on projects, and experienced mentorship, you’ll receive the training and support you need to run your own business and build a rewarding career.WHAT WE CAN OFFER YOU:Hourly Wage: $16/hour during the trainee period, which lasts up to 30 days.Upon completion of the trainee period, promotion to a Financial Representative with a $36,000 annual base plus unlimited monthly sales incentive.$1000 bonus after successful completion of trainee period and promotion to a Financial Representative.An education-based Accelerator Program designed to successfully transition you to an independent Financial Advisor.Benefits and Perks, 401(k) plan with a 2% company contribution and 6% company match.Regular associates working 40 hours a week can earn up to 15 days of vacation each year.Regular associates receive 11 paid holidays in 2025, which includes 2 floating holidays that are added to your prorated personal time to be used at your discretion.Regular associates are provided sick leave through the use of personal time. Associates working 40 hours a week can receive up to 40 hours of personal time in 2025, which is prorated based on the start date.Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.WHAT YOU'LL DO:You’ll participate in a comprehensive program to develop the skills required to provide holistic financial advice to clients. You will actively contribute to classroom discussion, participate in goal setting sessions and progress evaluation meetings.You’ll gain valuable direct sales experience in marketing Individual Insurance products to clients and pass a sales process competency test.You’ll cultivate and sustain prospecting skills such as research, targeting, networking, communication and more through use of personal networks, community events, and social media.You’ll acquire an in-depth understanding of our product offerings, demonstrating expertise in their features and benefits.You’ll oversee completion of content, proposals and paperwork flow throughout the field and Home Office, ensuring a seamless application and underwriting process.WHAT YOU’LL BRING:Successfully meet all trainee program requirements, gaining the skills and knowledge needed to excel.Obtain the required insurance licenses prior to starting the job, with up to two attempts allowed for the Life and Health exam.Pass the CRD/FINRA background check at hire and ongoing, with securities licensing required within 24 months of entry into the program.Be highly self-motivated and results-oriented, working both independently and as part of a team.Be able to travel up to 50% of the time, hold and maintain a valid U.S. driver's license, and have access to reliable transportation for meetings and appointments.You promote a culture of diversity and inclusion, value different ideas and opinions, and listen courageously, remaining curious in all that you do.PREFERRED:Knowledge of the Insurance/Financial Services industry, products and marketing practices.Bachelor's degree or equivalent preferred but not required.We value diverse experience, skills, and passion for innovation. If your experience aligns with the listed requirements, please apply!After applying, for inquiries about your application or the hiring process please email our Talent Acquisition area at . Need help Email UsApply Now Great place to workTogether we achieve greatness. Not only is this a core value, but it’s also representative of the kind of place we are built by the strength and integrity of our employees. It’s why we’re named a “Great Place to Work”.See All AwardsAn inclusive cultureSurround yourself with an authentic and inclusive culture. Your strengths and differences will be valued and celebrated by a diverse community of co-workers.Discover Our Culture Related Job OpeningsFinancial Business Consultant - Remote Remote | 503598 Financial Representative Trainee (Sales) - Des Moines, IA Iowa | 503425 Renewal Executive - Nashville, TN Tennessee | 503588

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Wisconsin’s Bank® as a Full-Time Teller! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: Process a variety of financial transactions (check cashing, withdrawals, deposits, loan payments, etc.) and accurately balance these transactionsOperate a teller drawer to serve customers and bank personnel in lobby or drive up.Recognize potential cross-sell opportunities and direct customers to appropriate bank personnel.Develop skills to recognize potential fraud and report to management as necessary. Comply with all department, bank and regulatory policies and procedures. Uphold established Wintrust culture.May be responsible for bank opening/closing and may be required to participate in community events.Qualifications:Minimum 6 months of experience in cash handling or customer serviceHigh school degree or equivalentTravel between branches may be necessaryMust be available to work all shifts including SaturdaysMust be able to lift 30 lbsMust be able to stand for long periods of timeBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimated hourly rate for this role is $18.00-$20.00/hr, along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Financial Representative Trainee (Sales)--Milwaukee, WILocation: WisconsinWork Type: Full Time RegularJob No: 503419Categories: Sales, Early Career Programs, Financial Representative TraineeApplication Closes: Open Until Filled SHARE Are you driven, self-motivated, and eager to jumpstart your career in the financial services industry We’re seeking passionate individuals to join our Accelerator Program, a dynamic trainee experience designed to set you up for long-term success. As a Financial Representative Trainee, you’ll embark on a comprehensive program that equips you with the skills and competencies necessary to excel in selling Individual Insurance products and building a sustainable, holistic financial practice. Through a combination of self-study, hands-on projects, and experienced mentorship, you’ll receive the training and support you need to run your own business and build a rewarding career.WHAT WE CAN OFFER YOU:Hourly Wage: $16/hour during the trainee period, which lasts up to 30 days.Upon completion of the trainee period, promotion to a Financial Representative with a $36,000 annual base plus unlimited monthly sales incentive.$1000 bonus after successful completion of trainee period and promotion to a Financial Representative.An education-based Accelerator Program designed to successfully transition you to an independent Financial Advisor.Benefits and Perks, 401(k) plan with a 2% company contribution and 6% company match.Regular associates working 40 hours a week can earn up to 15 days of vacation each year.Regular associates receive 11 paid holidays in 2025, which includes 2 floating holidays that are added to your prorated personal time to be used at your discretion.Regular associates are provided sick leave through the use of personal time. Associates working 40 hours a week can receive up to 40 hours of personal time in 2025, which is prorated based on the start date.Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.WHAT YOU'LL DO:You’ll participate in a comprehensive program to develop the skills required to provide holistic financial advice to clients. You will actively contribute to classroom discussion, participate in goal setting sessions and progress evaluation meetings.You’ll gain valuable direct sales experience in marketing Individual Insurance products to clients and pass a sales process competency test.You’ll cultivate and sustain prospecting skills such as research, targeting, networking, communication and more through use of personal networks, community events, and social media.You’ll acquire an in-depth understanding of our product offerings, demonstrating expertise in their features and benefits.You’ll oversee completion of content, proposals and paperwork flow throughout the field and Home Office, ensuring a seamless application and underwriting process.WHAT YOU’LL BRING:Successfully meet all trainee program requirements, gaining the skills and knowledge needed to excel.Obtain the required insurance licenses prior to starting the job, with up to two attempts allowed for the Life and Health exam.Pass the CRD/FINRA background check at hire and ongoing, with securities licensing required within 24 months of entry into the program.Be highly self-motivated and results-oriented, working both independently and as part of a team.Be able to travel up to 50% of the time, hold and maintain a valid U.S. driver's license, and have access to reliable transportation for meetings and appointments.You promote a culture of diversity and inclusion, value different ideas and opinions, and listen courageously, remaining curious in all that you do.PREFERRED:Knowledge of the Insurance/Financial Services industry, products and marketing practices.Bachelor's degree or equivalent preferred but not required.We value diverse experience, skills, and passion for innovation. If your experience aligns with the listed requirements, please apply!After applying, for inquiries about your application or the hiring process please email our Talent Acquisition area at . Need help Email UsApply Now Great place to workTogether we achieve greatness. Not only is this a core value, but it’s also representative of the kind of place we are built by the strength and integrity of our employees. It’s why we’re named a “Great Place to Work”.See All AwardsAn inclusive cultureSurround yourself with an authentic and inclusive culture. Your strengths and differences will be valued and celebrated by a diverse community of co-workers.Discover Our Culture Related Job OpeningsFinancial Business Consultant - Remote Remote | 503598 Financial Representative Trainee (Sales) - Des Moines, IA Iowa | 503425 Renewal Executive - Nashville, TN Tennessee | 503588

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Wisconsin’s Bank® as a Full-Time Teller! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: Process a variety of financial transactions (check cashing, withdrawals, deposits, loan payments, etc.) and accurately balance these transactionsOperate a teller drawer to serve customers and bank personnel in lobby or drive up.Recognize potential cross-sell opportunities and direct customers to appropriate bank personnel.Develop skills to recognize potential fraud and report to management as necessary. Comply with all department, bank and regulatory policies and procedures. Uphold established Wintrust culture.May be responsible for bank opening/closing and may be required to participate in community events.Qualifications:Minimum 6 months of experience in cash handling or customer serviceHigh school degree or equivalentTravel between branches may be necessaryMust be available to work all shifts including SaturdaysMust be able to lift 30 lbsMust be able to stand for long periods of timeBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimated hourly rate for this role is $18.00-$20.00/hr, along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Wisconsin’s Bank® as a Full-Time Teller! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: Process a variety of financial transactions (check cashing, withdrawals, deposits, loan payments, etc.) and accurately balance these transactionsOperate a teller drawer to serve customers and bank personnel in lobby or drive up.Recognize potential cross-sell opportunities and direct customers to appropriate bank personnel.Develop skills to recognize potential fraud and report to management as necessary. Comply with all department, bank and regulatory policies and procedures. Uphold established Wintrust culture.May be responsible for bank opening/closing and may be required to participate in community events.Qualifications:Minimum 6 months of experience in cash handling or customer serviceHigh school degree or equivalentTravel between branches may be necessaryMust be available to work all shifts including SaturdaysMust be able to lift 30 lbsMust be able to stand for long periods of timeMedical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimated hourly rate for this role is $18.00-$20.00/hr, along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Sign-on Bonus available for this role!Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Wisconsin’s Bank® as a full-time Relationship Banker! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: As a Relationship Banker, you will build and retain meaningful relationships with your customers, using your financial knowledge to recommend thoughtful solutions to meet their needs. In this dual role, you will contribute to the success of the branch by:Building lasting relationships with customers, discovering their financial needs and tailoring product and service recommendationsCollaborating with business partners (Mortgage, Wealth Management) to connect customers to experts who can help with specialized needsOperating a teller drawer serving customers in the lobby/drive-upOpening accounts, performing account maintenance and assisting customers with digital productsRecognizing potential fraud and other risksDepending on the shift, you might be responsible for bank opening/closingHelping support community and bank eventsQualifications:1-3 years of experience in a customer service, financial service, or sales roleHigh School Degree or equivalentIntermediate computer skillsBenefits:Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation:The estimatedhourly ratefor this role is $21.00-$28.00, along with eligibility to earn monthly commissions. Actualpayrate may vary based on several factors, such as a candidate’s qualifications, skills and experience.#LI-MG1#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.

Wintrust is a financial holding company with approximately $62 billion in assets whose common stock is traded on the NASDAQ Global Select Market. Guided by its “Different Approach, Better Results” philosophy, Wintrust offers the sophisticated resources of a large bank while providing a community banking experience to each customer. Wintrust operates more than 200 retail banking locations through 16 community bank subsidiaries in the greater Chicago, southern Wisconsin, west Michigan, northwest Indiana, and southwest Florida market areas. In addition, Wintrust operates various non-bank business units, providing residential mortgage origination, wealth management, commercial and life insurance premium financing, short-term accounts receivable financing/outsourced administrative services to the temporary staffing services industry, and qualified intermediary services for tax-deferred exchanges. Our unique business model is a competitive strength and value driver, powered by our talented colleagues who put our customers first and achieve better results for our clients.Wintrust was founded with the idea to be the alternative to the big banks. We are looking for top talent to join Chicago’s Bank® as a Part-Time Teller! Why join us An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 10 years) and Employee Recommended award by the Globe & Mail (past 6 years)Competitive pay and annual discretionary bonus eligibleComprehensive benefit package (for eligible employees) including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a fewFamily-friendly work hoursWith 175+ community bank locations, we offer opportunities to grow and develop in your careerPromote from within cultureWhat you’ll do: Process a variety of financial transactions (check cashing, withdrawals, deposits, loan payments, etc.) and accurately balance these transactionsOperate a teller drawer to serve customers and bank personnel in lobby or drive up.Recognize potential cross-sell opportunities and direct customers to appropriate bank personnel.Develop skills to recognize potential fraud and report to management as necessary. Comply with all department, bank and regulatory policies and procedures. Uphold established Wintrust culture.May be responsible for bank opening/closing and may be required to participate in community events.Qualifications:Minimum 6 months of experience in cash handling or customer serviceHigh school degree or equivalentTravel between branches may be necessaryMust be available to work all shifts including SaturdaysMust be able to lift 30 lbsMust be able to stand for long periods of timeMedical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet InsuranceCompensation: The estimated hourly rate for this role is $18.00-$20.00/hr, along with eligibility to earn an annual bonus. Actual pay rate may vary based on several factors, such as a candidate’s qualifications, skills, and experience.#LI-ONSITEFrom our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To be Chicago’s Bank® and Wisconsin's Bank®, we need to reflect that diversity both in all the communities we serve, the people we employ, the organizations we work with, and our banking and lending practices. 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, national origin, sex, sexual orientation, gender identity and expressions, genetic information, marital status, age, disability, or status as a covered veteran or any other characteristic protected by law.