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 ...