Outside Sales Representative – Winona, MN

Posted: 09/12/2025

Launchpad. Leadership Track. Life-Changing Work.

We believe work should be more than a paycheck — it should light you up. At Express Employment Professionals, we’re on a mission to brighten lives through fulfilling work, and we’re looking for our next Outside Sales Rep to join the team in Winona, MN.

This isn’t just a job — it’s a high-energy, high-impact, career-launching opportunity that can grow into a Market Leader and even Ownership Track position.


What You’ll Do
  • Discover: Ask powerful questions to uncover the root cause of client workforce challenges.
  • Solve: Offer consultative solutions that actually move the needle — not just sell a product.
  • Deliver Value: Share tools like leadership trainings, wage surveys, and market insights.
  • Own Your Territory: Manage a defined sales territory and visit 60+ businesses per week face-to-face.
  • Grow Your Book: Prospect, follow up, close deals, and build meaningful relationships.
  • Collaborate: Partner with your internal recruiting team to help employers hire great people.

Why This Role Rocks
  • Career Springboard: Our owners and managers (including your future boss) started in this role.
  • Autonomy + Flexibility: Run your own day with accountability, not micromanagement.
  • Purposeful Work: You'll literally be changing lives every week.
  • Leadership Path: Get coaching, training, and mentorship to grow into Market Leader.
  • High-Performance Culture: Grit, gratitude, growth mindset, and doing the right thing — these aren’t buzzwords, they’re how we operate.

What Success Looks Like
  • 2+ new clients per week
  • 120+ sales activities weekly (calls, visits, emails)
  • Use tools like CRM, territory plans, and Hit Lists like a pro
  • Deliver drop-offs that spark conversations and build trust

What You Need to Bring
  • Some sales, customer service, or hustle-heavy experience (restaurant, gym, cell phone sales, call centers — we’ve hired from them all)
  • No degree required (though we love lifelong learners)
  • Grit, optimism, coachability, and a self-starter mentality
  • Comfortable talking to strangers, building rapport, and hearing “no” without flinching
  • Valid driver’s license and access to a reliable vehicle

Compensation & Perks
  • Base salary: $48,000–$55,000 (depending on experience) + uncapped commission (seriously — sky’s the limit)
  • Clear path to $70K+ first-year OTE with strong performance; top reps in our company earn well into six figures over time
  • M–F schedule, no evenings or weekends
  • Health, dental, 401k match, PTO, and all the good stuff
  • Weekly training, annual retreats, and community impact events
 
Ready to make your mark? This role isn’t easy — but the reward is huge. Send your resume to Michael.Kreiling@ExpressPros.com today and start your path to leadership, ownership, and purpose-driven success.