Outside Sales Representative - Express Employment

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Located in Winona, MN

Salary: $55 - 60,000+

We’re not looking for just another salesperson.

We’re looking for a builder.

Client Growth Partner

B2B Sales | Winona, MN | Ownership Growth Path

📍 Winona, MN (local territory only)
💼 Full-Time | Monday–Friday, 8am–5pm
💰 $55,000–$60,000+ base + uncapped commission
🎯 Realistic OTE: $75k–$90k+


Why this role exists (and why now)

Winona is growing — and so are the businesses we partner with.

New client relationships.
Pre-planned local sales campaigns ready to launch.
Increasing demand from employers.

We need another strong relationship-builder in the field to keep momentum moving.


Who this role is built for

This is a relationship-first B2B sales role for someone who:

• Enjoys being out in the community talking with business owners
• Naturally creates energy, momentum, and buy-in
• Likes starting conversations and helping others see what’s possible
• Wants a long-term career in Winona — not a stepping stone

This is not a passive desk role.
It’s proactive, community-facing, and momentum-driven.

If your natural Working Genius is Galvanizing — you love rallying people, creating urgency, and getting ideas into motion — you’ll thrive here.

You don’t need staffing experience.
You do need confidence, follow-through, and comfort initiating conversations.


What you’ll be doing

• Building relationships with Winona-area employers and decision-makers
• Introducing businesses to flexible workforce and recruiting solutions
• Executing pre-planned local sales campaigns — you’re not starting from scratch
• Following up, staying organized, and keeping opportunities moving
• Partnering closely with our recruiting and operations team so clients feel supported, not sold to

This is not transactional sales.
It’s proactive, local, and people-driven.


Why people choose this role

• Local territory only — Winona and surrounding communities
• No overnight travel
• Monday–Friday daytime schedule
• Strong team support — you’re not on an island
• High-performance expectations — we keep score
• A service that genuinely helps businesses and job seekers
• Clear path to growth, leadership, and increased responsibility

Several of our leaders started in sales roles like this.
We promote from within — and we mean it.


Who tends to do well here

You might come from:

• Wireless or telecom sales
• Gym memberships or fitness sales
• Restaurant or retail management
• Inside sales or account management
• Any role where you were known as the person who could motivate others and make things happen

You don’t need:
• Staffing industry experience
• A perfect résumé
• To be the loudest person in the room

You do need:
• Drive
• Coachability
• Follow-through
• Comfort initiating conversations
• A genuine interest in helping Winona-area businesses and people succeed


About us

We’re a locally owned Express Employment Professionals office serving Winona and the surrounding region.

Our purpose is simple: brightening lives through fulfilling work.

Our values guide everything we do:

• Grit
• Growth mindset
• Gratitude
• Doing the right thing

We are a high-performing, team-driven office that believes growth is earned.

If that resonates, we should talk.


Next Step

Send your resume to:
📧 jobs.winonamn@expresspros.com

Or reach out directly to Mike:
📧 michael.kreiling@expresspros.com

We’re moving quickly and intentionally.

Express Office: Winona
1600 Gilmore Avenue
Winona, MN 55987
Apply Now