Demo

Benefit Organizer

Benefit Architects
North Chicago, IL Full Time
POSTED ON 10/13/2026
AVAILABLE BEFORE 2/10/2027

Benefit Organizer – Exclusive Chicago, Madison & Milwaukee Territory

Benefit Architects | Independent Contractor | Commission-Based

Build your business. Educate employees. Help families protect what matters most.

Benefit Architects is seeking an experienced, motivated sales professional to serve our exclusive territory covering Chicago, IL; Madison, WI; and Milwaukee, WI.

This opportunity combines access to an established employee market, recurring presentation opportunities, and ongoing support—with the independence and earning potential of a commission-based career.

About Benefit Architects

For more than 38 years, Benefit Architects has helped employees nationwide understand their benefits, identify coverage gaps, and explore options that fit their needs and budgets. Our product portfolio includes:

  • Life insurance
  • Disability insurance
  • Dental and vision coverage
  • Hospital indemnity insurance
  • Accident and critical illness insurance

What You’ll Do

  • Educate employees about their existing benefits and available supplemental coverage.
  • Conduct individual benefit consultations and recommend solutions based on each employee’s needs.
  • Lead presentations at new employee orientations and benefit events.
  • Build relationships with local leaders and workplace contacts.
  • Follow up with prospective clients, assist with enrollment, and provide ongoing service.
  • Manage and grow your business throughout the assigned territory.

What We Offer

  • Exclusive territory: Serve as the designated agent for our Chicago, Madison, and Milwaukee markets.
  • Access to thousands of prospective clients: Connect with employees in an established market.
  • Recurring presentation opportunities: Present at new employee orientations every two to four weeks.
  • Training and ongoing support: Develop your product knowledge, presentation skills, and sales process.
  • Sales and marketing resources: Tools and materials to support outreach, education, and enrollment.
  • Competitive insurance products: Access to established carriers and a broad range of coverage options.
  • Uncapped earning potential: Potential annual commission earnings of $50,000–$200,000 , depending on sales performance. This is a commission-only opportunity; earnings are not guaranteed.
  • Independent contractor flexibility: Manage your schedule and take ownership of your business.

What You Bring

  • At least two years of sales experience, preferably in insurance.
  • An active life insurance license.
  • Strong communication, relationship-building, and presentation skills.
  • The confidence to lead group presentations and conduct individual consultations.
  • Consistent follow-through, strong organizational skills, and a self-directed approach.
  • A commitment to helping employees make informed benefit decisions.
  • Ability to travel throughout the assigned territory for presentations, events, and appointments.

Ready to Grow With Us?

If you enjoy building relationships, educating clients, and turning opportunity into results, we’d like to hear from you.

Apply with your résumé and a brief summary of your sales experience.

Job Type: Full-time

Pay: $50,000.00 - $250,000.00 per year

Benefits:

  • Flexible schedule

Experience:

  • Sales: 2 years (Required)

License/Certification:

  • Life Insurance License (Required)

Work Location: On the road

Salary : $50,000 - $250,000

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