Outside Sales Representative

Group Management Services, Inc.; Pittsburgh (Allegheny County); Hybrid; USD 50,000 - 65,000; Full time

Benefits offered by this job

Medical with HSA match

FSA

Dental

Vision

401(k) match

Disability

Employee Assistance Program

Hybrid/flexible scheduling

Job summary

Group Management Services, Inc. is hiring Outside Sales Representatives to prospect, present, and close deals for a leading PEO. You will own your book of business and leverage hybrid scheduling to drive growth in your region.

Expect a base salary of $50K-$65K with uncapped commissions and KPI bonuses, plus a comprehensive benefits package including medical, dental, vision, 401(k) match and more. Strong training and leadership opportunities await high‑performers.

Qualifications

• High-energy, coachable and driven sales professional.
• Strong desire for structured sales training and career growth.
• Ability to build and manage a book of business.

Responsibilities

• 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 and close deals.
• Propose tailored solutions to meet client needs.
• Create value by helping small businesses grow and succeed.

Skills

Prospecting

Cold calling

Sales cycle management

Negotiation

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:

• $50K-$65K 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.