Outside Sales Representative

Group Management Services, Inc.; Chicago (IL); Hybrid; USD 60,000 - 75,000; Full time

Benefits offered by this job

Base salary $60K-$75K

Uncapped commissions

Full benefits

Leadership training

Hybrid scheduling

Ownership of book

Job summary

Group Management Services, Inc. (GMS) is seeking Outside Sales Representatives in the Chicago area.

You will lead the full sales cycle from prospecting to contract, meeting decision-makers, and presenting tailored solutions to help businesses become simpler, safer, and stronger. We offer a $60K-$75K base salary with uncapped commissions, comprehensive benefits, and top-tier training, including a Leadership Academy.

Responsibilities

• 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

Skills

Resiliency

Coachability

Grit

Ownership mindset

Job description

GMS is hiring Outside Sales Representatives!

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
• Full benefits: Medical (with HSA match), FSA, Dental, Vision, 401(k) match, Disability, EAP, and more!
• 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:

• 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.

Group Management Services is an Equal Opportunity Employer.