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