Weekend Remote Technology Sales Jobs in Madison, WI

Ready to jump-start your career and take charge of your earning potential? At Platinum Supplemental Insurance, we’re looking for motivated individuals ready to learn, grow, and thrive in a fast-paced environment. Whether you’re a recent grad or simply seeking a fresh challenge, this is your chance to earn like a highly educated professional—our proven products and systems are your roadmap to becoming a top earner in sales. If you’re prepared to unlock your full potential, let us show you how to build a lucrative and rewarding future.

Why Join Platinum?

Four-Day Workweek

Travel Monday–Thursday to meet with farmers and small business owners, then enjoy your weekends off. Say goodbye to the daily grind and hello to a work-life balance that lets you recharge and spend time on what matters most.

Uncapped Earning Potential

This is a commission-based role, and many of our new reps earn $75,000 or more in their first year, with top performers exceeding $100,000. The sky truly is the limit when it comes to your income.

Ongoing Support & Resources

Focus on building relationships and closing deals while Platinum handles marketing, recruiting, back-office support, and customer service. You’ll also benefit from generous bonuses, annual renewal income, and luxury travel incentives for high achievers.

Cutting-Edge AI Training

Get an edge on the competition with our new AI-driven training platform. You’ll receive personalized feedback, interactive coaching, and real-time support to help you master Platinum’s proven 10-step sales system—faster and more confidently than ever before.

Your Day-to-Day

1. Travel to Your Territory: Meet potential customers (farmers, small business owners, and families) face-to-face to build trust and educate them about Platinum’s supplemental insurance solutions.

2. Leverage Our 10-Step Sales Process: Follow a time-tested system that helps you identify prospects, deliver compelling presentations, and close more sales—backed by our powerful AI training.

3. Stay Motivated & Collaborate: Work within a supportive, team-based culture that celebrates wins, shares best practices, and drives everyone to reach new heights.

What You’ll Enjoy

• High Earning Potential, No Caps: Earn based on your performance and ambition, without hitting a salary ceiling.
• Residual Income: Benefit from ongoing earnings long after closing a sale, creating a steady income stream.
• Advancement Opportunities: Rise quickly through the ranks and take on leadership roles as you prove your abilities.
• Quarterly Vacations: Earn the chance to recharge on exciting getaways with fellow top performers.
• Company Trips & Events: Enjoy travel and experiences on us—bring a significant other along, all expenses paid.
• Weekends Off: A Monday–Thursday work schedule means you get every weekend free for family time or relaxation.

Who Thrives Here

• Go-Getters: You bring the hunger, discipline, and drive needed to excel in a commission-based environment.
• Clear Communicators: You can connect with people from various backgrounds, build trust, and explain concepts in a simple, relatable way.
• Continuous Learners: You’re excited to leverage AI-based training and mentorship to refine your skills and grow quickly.
• Flexible Travelers: You’re comfortable with overnight travel Monday–Thursday and are 18+ years old.

Ready to Take the Leap?

If the idea of earning what you’re worth, mastering an innovative sales system, and enjoying a 4-day workweek excites you, we’d love to hear from you! Apply today and discover how Platinum can help you unlock a thriving career in sales.

About Platinum

Platinum Supplemental Insurance specializes in helping individuals, families, and businesses secure their financial futures through supplemental coverage. By bridging the gaps left by traditional health plans, Platinum’s products offer peace of mind when unexpected health issues arise. With a people-first mentality, robust training programs, and a commitment to growth, Platinum provides the ideal environment for sales professionals to excel—no matter where they’re starting from.

Join the Platinum team and see for yourself why so many have launched fulfilling, lucrative sales careers with us.