Overview
Outside Sales Representative Jobs in Chicago at BlockRock South LLC
Overview
We’re building out our Chicago market team and looking for driven individuals who want to take ownership of a territory, build local partnerships, and grow a revenue stream they can directly influence.
This is a field-based role focused on developing business relationships and expanding location-based revenue programs across small and mid-sized businesses.
If you’re someone who prefers autonomy, enjoys being out in the field, and wants a clear path to higher earnings, this role is designed for you.
What You’ll Be Responsible For
- Manage and develop a defined regional territory (approx. 150–200 miles)
- Engage with local business owners through in-person outreach
- Identify opportunities and introduce revenue-generating service programs (vending/coin-op/POS solutions)
- Build and maintain long-term business relationships
- Balance company-provided opportunities with self-generated outreach
- Track pipeline activity and follow-ups using CRM tools
- Continuously expand your territory footprint and close new business
Compensation & Perks
- Base salary: $40K–$60K
- Uncapped earnings tied directly to performance
- Quarterly incentive bonuses
- Travel reimbursement (mileage, tolls, parking)
- Paid onboarding + ongoing coaching in the field
- Health benefits and PTO
- Monday–Friday schedule (daytime hours)
- Clear advancement opportunities as you grow performance
Who This Role Fits Best
- Comfortable initiating conversations with business owners
- Background in field sales, canvassing, route-based roles, or strong motivation to break into sales
- Self-directed and disciplined in managing daily activity
- Resilient and able to stay consistent through rejection
- Motivated by performance-based income and growth
Additional Details
- Full-time, field-based position
- Background check required during hiring
Pay: $40,000.00 – $100,000.00 per year
Benefits:
- Health insurance
- Paid training
- Referral program
- Travel reimbursement
Application Question(s):
- What are your base salary expectations annually?
Work Location: On the road
Title: Outside Sales Representative
Company: BlockRock South LLC
Location: Chicago
