Outside Sales Representative - Express Employment

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Located in Winona, MN

Salary: $55 - 60,000+

Client Growth Partner (B2B Sales | Winona Area | Training Provided)
📍 Winona, MN (local market only)
💼 Full-Time | Monday–Friday, 8am to 5pm
💰 $55,000 to $60,000 base + commission (OTE $75k–$90k+)
Why this role exists (and why now)
Winona is growing—and so are the businesses we partner with.
Between new client relationships, upcoming sales campaigns already planned for the Winona market, and increasing demand from local employers, we’ve reached a point where 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 and talking with local 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 that requires relocating
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 forward
  • Partnering closely with our Winona recruiting and operations team so clients feel supported, not sold to
This is not transactional sales.
It is proactive, local, and people-driven.
Why people choose this role
  • Local territory only – Winona and surrounding communities
  • No overnight travel
  • Monday–Friday schedule, day time hours
  • Strong team support—you’re not on an island
  • A service that genuinely helps businesses and job seekers in the community
  • 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.
Compensation & benefits
  • $55,000 base salary
  • Uncapped commission (realistic OTE: $75k–$90k+)
  • Health, PTO, and additional benefits
  • Structured training, coaching, and ongoing support
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
  • 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
If that resonates, we should talk.
Next step
We’re moving quickly and intentionally. Please send you resume to jobs.winonamn@expresspros.com or hit "apply now" to submit an application!

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