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
Recommended Jobs
Precision Mechanical Assembly Technician
A day in this role As a Precision Mechanical Assembly Technician at W. H. Leary, you’ll be a hands-on builder who keeps production and operations moving. Your day blends craftsmanship, accuracy, a…
Chief Financial Officer - To $170K - Chicago, IL - Job # 3676B
Chief Financial Officer – To $170K – Chicago, IL – Job # 3676B Who We Are The Symicor Group is a boutique talent acquisition firm based in Schaumburg, IL & Rockport, TX. Our nationally unique value …
Area Manager (Chicago/Indy Area)
See yourself here. Onsite Women's Health is on a mission to improve women's healthcare. In partnership with forward-thinking providers across the country, Onsite Women's Health offers comprehen…
Chief Operating Officer - Hospital (Relocate to West Coast)
Job Description Job Description -- APPLICANTS MUST BE WILLING TO RELOCATE TO COASTAL OREGON -- Vivo HealthStaff is actively recruiting for a Chief Operating Officer (COO) position in a prominent…
Cardiology - Advanced Practice Provider
Overview: Carle Health is seeking a Cardiology Nurse Practitioner or Physician Assistant to join our Cardiology Group in Peoria, Illinois. Opportunity Details: Join an established and well-respec…
Associate Veterinarian - Part-Time
Overview: Looking for a consistent part-time schedule where you can practice confidently without full-time demands? Willow Ridge Animal Hospital is seeking an experienced veterinarian to join ou…
Assistant Project Manager
Job Title: Field Engineer Job Description The Field Engineer will work on-site at natural gas compressor station projects, ensuring that natural gas remains pressurized as it travels through pi…
Massage Therapist
Job Description Job Description Description: Job Description: Massage Therapist We are seeking a skilled and compassionate Massage Therapist to join our team. As a Massage Therapist, you will…
Family Medicine Physician - $350000.00
A thriving healthcare system seeks a Family Medicine Physician in Danville, IL (Less than 35min from Champaign 2h and Chicago)! Other locations available. Come make a difference within a growin…
Healthcare Solution Analyst, Clinical Analytics Solutions (Hiring Immediately)
Job Family : Data Science Consulting Travel Required : Up to 10% Clearance Required : None ? What You Will Do : A key part of Guidehouse's work with healthcare client…