Financial Representative Trainee; Sales - Chicago. IL

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.

• Step into a career with earnings from $36,000–$75,000 in your first year, plus uncapped incentives once you complete training – where your effort determines your earnings!
• $1,000 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.
• 401(k) plan with a 2% company contribution and 6% company match.
• Work‑life balance with vacation, personal time and paid holidays. See our benefits and perks page for details.
• Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.

• 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.

• 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.

• 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

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