Chicago Sales Representative

Workstream; Rosemont (IL); Hybrid; USD 60,000 - 75,000; Full time

Benefits offered by this job

Base salary $60K‑$75K (depending on経験)

Uncapped commissions

3 weeks PTO + 8 holidays

Full benefits: Medical, FSA, Dental, V

401(k) match

Disability, EAP

Mileage, cell phone & gym

Top-tier training

Leadership Academy

Hybrid/flexible scheduling

No assigned territories

Job summary

Group Management Services is seeking Outside Sales Representatives to drive 100% B2B new business development. You will prospect, manage the full sales cycle from cold call to contract, and meet with decision-makers to present solutions that make businesses simpler, safer, stronger.

Earn a base salary of $60K-$75K with uncapped commissions, KPI bonuses, and generous PTO. Enjoy full benefits, mileage & gym reimbursements, top-tier training, and hybrid scheduling based on tenure and performance.

Qualifications

• Thrive in a fast-paced entrepreneurial environment with persistence.
• Demonstrate resiliency, coachability and grit in evolving markets.
• Maintain a strong personal motivation and clear reasons for success.

Responsibilities

• 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 and in-person meetings.
• Meet with decision-makers to present solutions that make businesses simpler, safer, stronger.
• Propose constructive solutions tailored to prospective client needs.
• Create tangible value by positively impacting small businesses in your community.

Skills

Resiliency

Coachability

Grit

Strong why

Negotiation

Cold calling

Job description

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.

Group Management Services is an Equal Opportunity Employer