B2B Field Sales Representatives
Chicago, IL | Field-Based
Base $40,000 + Uncapped Commission | Realistic Earnings $75K–$110K+
As businesses look ahead to the new year, we’re expanding our Chicago field sales team and hiring self-motivated reps who want meaningful earnings, real autonomy, and a career they can grow into, not just another job.
What You’ll Do
- Own a Chicago – regional territory (typically 100–200 miles)
- Visit local small businesses daily (this is an outside, field-based role)
- Prospect, build relationships, and pitch vending / coin-op / POS revenue programs
- Work a blend of leads + self-sourced walk-ins
- Track outreach & follow-ups through CRM
- Build routes, expand business relationships, and close deals
Compensation & Benefits
- $40,000 base salary
- Uncapped commission with realistic first-year earnings of $75K–$110K+
- Bi-yearly performance bonuses
- Travel reimbursement (gas, tolls, parking)
- Paid training & ongoing field development
- Health benefits + PTO
- Monday–Friday field schedule (days only, no weekends)
- Career growth pathway
You’ll Succeed Here If…
- You’re comfortable walking into businesses and starting conversations
- You’ve done route sales, field sales, canvassing, or territory work, or want to prove yourself with the right training
- You thrive independently and stay disciplined with activity
- You can handle rejection, stay positive, and keep moving
- You like seeing your work directly tied to income
If you want to start the year in a role with real earning potential and structure to help you win , we’d like to speak with you.
Full-time | Field Based | Background check required during hiring
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