Independent Sales Associate

The Benefits Boss
Chicago, IL

Job Description

Job Description

Are you ready to take control of your career, work from anywhere, and make a real impact helping individuals and families protect what matters most? The Benefits Boss is on the lookout for driven, positive, and self-motivated professionals to join our growing team as Independent Sales Associates!

We specialize in empowering people with better health, life, and supplemental benefits—tailored to their unique needs. If you’re passionate about people, love the thrill of sales, and want to work in a supportive, energetic environment where your success is in your hands—we want to hear from you.

What You’ll Do:

  • Connect with high-intent prospects virtually and guide them through options that actually make a difference

  • Build long-term relationships based on trust, transparency, and value

  • Manage your own pipeline and schedule

  • Embrace training and mentorship designed to help you level up fast

  • Stay committed to a full-time schedule, giving your clients and your success the attention they deserve

What’s In It For You:

  • All Commission + Performance Bonus – No cap on what you can earn! Earn a $25/hour bonus for each talk time hour, plus a monthly bonus of up to $5K

  • Fully remote – Work from your home office, a coffee shop, or wherever you thrive

  • Proven system & mentorship – We’ll set you up for success from day one

  • Freedom & flexibility – Grow at your pace, and take charge of your income

What We’re Looking For:

  • Active health insurance license—It is recommended that you hold licensing in 15 states; however, we provide support to help you ramp up to this number or expand to all 50 states.

  • Tech-savvy with proficiency in digital communication tools and CRM systems.

  • A self-starter with a professional work ethic and commitment to a full-time schedule

  • Sales experience is a plus—but a great attitude and strong work ethic matter more

If you're ready to build a meaningful career helping others while enjoying unmatched flexibility and income potential, apply now. At The Benefits Boss, we don’t just sell insurance—we help people live better lives.

Posted 2025-07-28

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