Outside Sales Representative
$60k - $75kGroup Management Services, Inc.
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.
- ...team that always delivers! Why Join Us?: * Sell essential, recession-resistant services * Represent a trusted brand with high customer retention * Be part of a supportive sales team that offers consistent 1:1 coaching, ongoing sales learning, and real growth...SuggestedRelocation package
- ...ideal candidate will prospect and generate new commercial business as well as perform cold-calls in the field to generate new permanent sales. This candidate should be able to support existing clients and have an ability to conduct product demonstrations....SuggestedPermanent employmentFull time
- ...Outside Sales Representative – Unlimited Commission Potential Schaeffer Manufacturing Company – (Remote, 1099 Position) Grow Your Own Business with Schaeffer Oil! Join Schaeffer Oil — a trusted American-made brand with over 185 years of proven performance in...SuggestedFor contractorsLocal areaRemote work
- ...ranked #59 of 500 solution providers CRN’s Tech Elite 250 Job Summary: We are looking for a strong and determined Outside Sales Representative to generate new business opportunities for our Systems and Network Integration team. To be successful in this role, you...SuggestedFull timeFlexible hours
$200k
...Sales Consultant About Us Encore Concrete Coatings is a Midwest-based concrete coating company that specializes in transforming concrete... ...concrete coating industry Why This Job? Elite pay for an outside sales job Uncapped earnings potential Get paid instantly...SuggestedWeekly payFull timeWork at officeImmediate startWork from homeRelocationFlexible hours1 day per week$60k - $75k
...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...Full timeContract workFlexible hours$90k
...opportunity. Employees are empowered to represent a superior telecommunications company while... ...early applications for our Direct Sales Representative MDU class starting in December... ...Six Figures! ***Door-to-Door Residential Outside Sales*** Take control of your income in...Full timeContract workLocal areaFlexible hours$40k
...Sales Development Representative – High Earnings & Career Growth with Global Audio Branding Leader Location: 401 N Michigan Ave, Chicago, IL 60611 Starting Salary: $40,000 Sales Development Representatives have opportunities for base salary increases up to $80,...Full timeWork at officeWork from home- ...and establish long-term relationships. Responsibilities Drive top-of-the-funnel lead generation for account executives and sales managers Update and manage all sales activities, opportunities, and account information in CRM Consistently achieve monthly quota...Full timeWork experience placement
- ...as an extension of our clients' brands, we help them grow sales, optimize operations, and embrace digital transformation.... ...customer relationships and build lasting success. The Outside Sales Representative role emphasizes in-person customer engagement, proactive relationship...Permanent employmentFull timeWork experience placementWork at office
- ...as an extension of our clients' brands, we help them grow sales, optimize operations, and embrace digital transformation.... ...customer relationships and build lasting success. \n \n The Outside Sales Representative role emphasizes in-person customer engagement, proactive...Permanent employmentFull timeWork experience placementWork at office
- ...We are hiring for a Sales Development Representatives (SDR) and an Enterprise Lead to join our client's growing sales teams in Chicago. SDR role: The ideal candidate has 6+ months of SaaS SDR/BDR experience and is excited about building pipeline and driving new conversations...Full timeWork at office
- ...memorable experience to all guests and prospective customers. This role is vital to our brand and supports the Store Manager in achieving sales goals and operational objectives. Brand Ambassadors are responsible for being the guardians of the brand and furthering the...Full timeWork at office
$41.6k
...Job Description Benefits: ~401(k) ~ Competitive salary ~ Dental insurance ~ Health insurance Job Posting: Outside Sales Representative Company: Chicago Glass and Mirror Location: Chicago, IL Position Type: Full-Time Salary: $41,600 per year (plus...Full timeFor contractors$1,700 - $4,500 per week
...Outside Sales Representative - $1700 - $4500/Week Full-Time | In-Home Sales | Warm Leads Provided | Commission-Only | $90,000–$250,000+ Annual Earning Potential Are you a driven sales professional with a passion for connecting with people and delivering exceptional...Full time- ...with experience — uncapped earning potential Reports To: Sales Leadership, Windrock Enterprises About Windrock... ...Windrock Enterprises is hiring an experienced, motivated Outside Sales Representative to own and grow the Chicagoland and broader Illinois market...Base plus commissionFull timeFor contractorsFor subcontractorWork at officeLocal area
$65k - $75k
...you rather than slow you down. If you want real ownership, a direct line to how the company grows, and a path to build a career in sales, keep reading. About Us - Our Mission & Vision At Autopilot, our mission is to free people up to do what they do best by automating...Full timeWork at officeFlexible hoursShift work$100k - $250k
...Trips Spiff Programs Training Program. JOB DESCRIPTION Most sales jobs hand you a ceiling and a script. We hand you a territory... ...industry average. Family owned and run by the Tegeders since 1977 not outside investors. Steady enough to build a career on growing fast...Full time$120k - $250k
...AmeriPro Roofing , an industry-leading name in exterior home remodeling for over two decades, is immediately hiring Outside Sales Representatives. In this role, you will be the face of our brand, using direct, door-to-door canvassing to connect with local homeowners...Full timeFor contractorsWork at officeLocal areaImmediate startDay shiftAfternoon shift- ...window and door business and are looking for an experienced outside sales professional who enjoys building something from the ground up... ...capabilities across the continental United States. You’ll represent a broad portfolio of vinyl, wood, and composite windows and...For contractors
- ...Roofing #WeAreNotTheSame Infinity is currently seeking highly-motivated, professional, detail-oriented individuals to join our roofing sales team as an independent seller. Coming on board as an independent seller with us, you will be trained and given all the tools...For contractors
- ...Job Description Job Description We are looking for an efficient Outside Sales Representative to join a growing healthcare team in Oak Brook, Illinois. This Long-term Contract position is ideal for someone who thrives in face-to-face interactions, enjoys being active...Long term contractLocal areaFlexible hours
- ...About This Role The Ace for Business Outside Sales Representative supports Ace Hardware Corporation's B2B growth strategy by engaging business customers, developing sales opportunities, and helping connect those customers with products, services, and solutions available...Local areaFlexible hoursNight shift
$60k - $80k
...Job Description Job Description Title: Outside Sales Consultant Location: Chicago, IL Are you a driven, energetic, and helpful sales professional looking to make great money? Work with one of Forbes’ America's Best Midsize Employers* and be rewarded for your...Weekly payContract workFor contractorsNight shiftWeekend workAfternoon shift- ...Field Sales Associate Field Sales Associate closes sales through face-to-face interaction with customers based within assigned sales territories. Responsibilities: Make a significant positive impact on sales and improving the consumer buying experience Maintain...Work experience placement
$5,000 per month
...Job Description Job Description Title: Outside Sales Representative - $5,000 NEW CONSULTANT COMMISION BONUS Territory Location: Chicago, IL area Are you a driven, energetic, and helpful sales professional looking to make great money? Work with one of Forbes...Weekly payContract workFor contractorsWeekend workAfternoon shift- ...Outside Sales Representative Beacon Funding is seeking an Outside Sales Representative to build and expand vendor, dealer, and partner relationships across a national territory. This is a true field-based role focused on face-to-face relationship building and long-...Base plus commissionFlexible hoursNight shift
$150k - $300k
...Generator Sales Specialist We're looking for a proven closer ready to take ownership of a high-opportunity territory. This is a 100% commission role for self-motivated sales professionals who want uncapped earning potential and thrive in a performance-driven environment...Flexible hours$40k - $67.76k
...Outside Sales Representative - Ground Protection Sunbelt Rentals--the fastest growing rental business in North America--is seeking an Outside Sales Representative - Ground Protection. The Outside Sales Representative's primary mission is to develop and maximize Ground...Full timeTemporary workLocal areaFlexible hours$120k - $150k
...Outside Sales Representative Kitchen Guard is expanding into the Chicagoland area, and we're looking for a driven professional to play a key role in our growth. If you're ready to apply your technical expertise and sales skills to help businesses stay safe with industry...Work at officeLocal area
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Outside Sales Representative. Be the first to apply!
- food service sales representative Chicago, IL
- group sales representative Chicago, IL
- software sales executive Chicago, IL
- roofing sales representative Chicago, IL
- sales specialist Chicago, IL
- senior sales representative Chicago, IL
- commercial specialist Chicago, IL
- outside sales representative Chicago, IL
- new home sales consultant Chicago, IL
- virtual sales representative Chicago, IL







