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