Discover a Career with Five Star Benefits

Outside Sales Representative

| Hybrid | $65,000–$120,000 + Bonuses

Location: St. Cloud, MN (Hybrid – some travel required)
Compensation: $65,000–$120,000 annually
Bonus: Monthly & quarterly performance bonuses + residual income
Perks: Flexible schedule, incentive trips, tech provided, training included

Make an Impact Helping Local Businesses Thrive

Are you a strong communicator who thrives on building relationships and providing top-notch support? Join Five Star Benefits, where we deliver innovative benefits solutions to small and mid-sized businesses across the region. As an Outside Sales Representative, you’ll help business owners navigate benefits options and ensure they get the service they deserve.

What You’ll Do:

• Act as the primary contact for existing and new clients
• Provide product support and help clients navigate benefits solutions
• Schedule and attend client meetings (some in-person travel required)
• Ensure smooth onboarding, policy follow-ups, and renewals
• Build long-term client relationships through consistent service and follow-up

Why Join Five Star Benefits?

• Competitive Pay: $65,000–$120,000 (DOE)
• Bonuses: Monthly and quarterly incentives + residual income
• Hybrid Flexibility: Work from home and in the field
• Paid Training: Licensing support provided if needed
• Tools Provided: iPad and other tech included
• Incentives: Quarterly and annual company trips
• Autonomy: Manage your schedule and work independently
• Growth: Be part of a company that promotes from within

What We’re Looking For:

• Excellent communication, organization, and time management skills
• Self-starter with a service mindset
• Valid driver’s license and reliable vehicle
• Prior customer service, sales, or client-facing experience a plus
• Interest in insurance or benefits a bonus (but not required)

Ready to Make a Difference?

If you’re looking for a flexible, rewarding role where your work truly matters — we’d love to meet you. Apply today and let’s build something great together.