Demo

Rep Development Program: Sales Trainee

The Cason Group
Chicago, IL Full Time
POSTED ON 5/7/2026
AVAILABLE BEFORE 7/6/2026

The Cason Group serves insurance professionals by delivering creative sales and service solutions that exceed expectations through Group Benefits, Individual Medical, and Financial Services.


Job Title: Rep Development Program: Sales Trainee

Division: Group Benefits, Financial Services, or Individual Medical

Location: Initial Training (12-18 Months) will occur in Columbia, SC; Charlotte, NC; Raleigh, NC; Atlanta, GA; Nashville, TN

Relocation may be required after successful completion of initial training; potential locations include: Richmond, VA; Cincinnati, OH; Tampa, FL; Houston, TX; San Antonio, TX, or other location TBD

Type: Full-Time; May require occasional overtime, including evenings and weekends; Travel is required

Hiring Range: $45,000 - $65,000 annual salary (includes base salary plus quarterly guaranteed bonus with the opportunity to grow after successfully completing the initial training period)

Commitment: Three-Year Commitment to The Cason Group

Our Sales Trainee Rep Development Program (RDP) provides in-depth career training to our future TCG Sales Reps offering business and professional development while educating Trainees about the industry. Successful completion of the RDP will result in placement as a Sales Rep/Regional Consultant in a specified location.

What Our Sales Trainees Do:

  • Consult and Collaborate: work with various departments to learn and perform aspects of TCG operations and sales-support roles
  • Coordinate and Communicate: communicate regularly with Sales Representatives on prospecting, appointments, and advising agents and clients
  • Drive Results: pass all RDP certifications; perform with excellence in meeting departmental metrics
  • Stay Current in Industry: successfully obtain relevant Life and Health Insurance licensures; maintain up-to-date knowledge of products, carriers, quoting requirements, prescreening, underwriting guidelines, and TCG procedures

What We Are Looking For:

  • Bachelor’s Degree or equivalent experience in a related field
  • Excellent communication, interpersonal, and customer services skills as it relates to positively influencing and persuading others
  • Ability to develop and deliver effective sales presentations
  • Strong attention to detail and accuracy along with compliance of deadlines while managing and prioritize multiple tasks simultaneously
  • Proficiency in Microsoft Office (Outlook and Teams); knowledge of databases
  • Visibility requires maintaining a professional appearance and positive company image while interacting with the public

Why You Should Work With Us:

  • Excellent Benefits: Health, Dental, Vision, Life, and Disability insurance options
  • 401K Retirement Plan with company contribution
  • Paid Time Off (vacation and holidays)
  • Employee Assistance Program
  • Charitable Matching and Paid Community Service Time

Salary : $45,000 - $65,000

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