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