Chicago Sales Representative

GMS is hiring Outside Sales Representatives! One of the nation’s leading PEOs is looking for high‑energy hunters ready to build a career with uncapped earning potential.

What’s a PEO?

A Professional Employer Organization helps businesses grow by handling payroll, benefits, workers’ comp, and HR. It’s a $176B+ industry growing at ~14% annually and serving 2–3 million employees nationwide.

Why You’ll Love It Here:

• $60K-$75K base salary depending on experience/location
• Uncapped residual commissions + KPI bonuses
• 3 weeks PTO + 8 paid holidays
• Full benefits: Medical (with HSA match), FSA, Dental, Vision, 401(k) match, Disability, EAP, and more!
• Mileage, cell phone & gym reimbursement
• Top‑tier training + Leadership Academy for internal growth opportunities
• Hybrid/flexible scheduling earned with tenure + performance
• No assigned territories — build your region your way

Our Outside Sales Representatives:

• Thrive in a fast‑paced entrepreneurial environment
• Have resiliency, coachability, grit, and a strong “why” behind what they do
• Seek continuous structured sales training in negotiation, objection handling, closing
• Are motivated by recognition — incentive trips, awards, leadership opportunities
• Want ownership – own your book of business and directly control the ability to write your own paycheck

What You’ll Do:

• 100% B2B new business development
• Prospect and manage the full sales cycle from cold call to contract
• Daily hunting for new prospects via cold calling + in person intro meetings
• Meet with decision‑makers to present solutions that make businesses Simpler, Safer, Stronger
• Propose constructive solutions tailored to the prospective client’s needs
• Create tangible value by positively impacting small businesses in your community

Why GMS?

At GMS, it’s not just what we do — it’s why we do it. Our mission is simple: help small businesses thrive. For over 30 years, our co‑employment model has saved clients time, reduced costs, and provided peace of mind for thousands of businesses nationwide. We take a people‑first approach, pairing exceptional customer service with innovative, cutting‑edge technology to drive efficiency and deliver real world impact.

Take your career to the next level and own your future. Apply today!

Learn more:

Group Management Services is an Equal Opportunity Employer

GMS is a professional employer organization (PEO) and a Benefits Administrator. We serve companies of all sizes nationwide. GMS was founded by Mike Kahoe in 1996 and has helped thousands of companies take control of their HR functions.
As HR professionals, we take on the administrative burdens that companies don’t have the time or expertise to manage effectively, including:
Payroll And Tax
Human Resources
Employee Benefits
Risk Management
Benefits Administration (for insurance brokers)
We make employee management simpler, safer, and stronger. We save you time and money. You retain full control over your employees, and regain the opportunity to focus on growing your business. Leave the HR details to us.