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Sales Executive - Mid Market

Paychex

Chicago, ILJob$75–150K/yrSeen todaySeen in employer's feed today

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At a glance

Compensation
$75–150K/yr
Location
Chicago, IL
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Requirements

Credentials this posting asks for.

Driver's License, required

Job overview

Paychex is seeking a Sales Executive to grow its client base by selling workforce management products and services. The role develops new clients, identifies customer needs, presents solutions to decision makers, and builds referral relationships. The position focuses on increasing revenue and market share through prospecting, customer analysis, and follow-through on sales and service needs.

Skills & qualifications

RequiredNice to have

Skills

Outside Sales, nice to haveCold Calling, nice to haveCRM Software, nice to have

Qualifications

High School Diploma, requiredBachelor's Degree, nice to have5 Years Outside Sales Experience, nice to have4 Years HCM Industry Experience, nice to haveDriver's License, required

Benefits

Medical Insurance
Tuition Assistance
401(k) Match
Paid Time Off

Full job description

Paychex is reimagining how businesses manage their workforce by bringing payroll, HR, benefits, and advisory services together into a single connected HCM platform. As Paychex and Paycor come together, we're combining innovative technology, data-driven insights, AI, and human expertise to help organizations work smarter, support their people, and achieve better business outcomes. This is an exciting time to join our team as we continue to invest in innovation, simplify client experiences, and shape the future of work. At Paychex, you'll have the opportunity to grow your career, make a meaningful impact, and be part of something bigger as One Paychex.

Overview

Selling Company's products and services by developing new clients and increasing the client base to increase profits in the Core Sales, Human Resource Services Sales or Major Market Sales organizations.

Responsibilities

  • Leverage the Go-to-Market Sales Strategy to identify customers’ needs and present the Paychex solution to key stakeholders and decision makers in accordance with the client’s preference on in person or virtual interaction to increase revenue and market share.

  • Scheduling appointments and visiting potential and current referral sources to secure referrals to end users.

  • Prospecting for new clients and new referral sources utilizing the telephone, direct mail, seminars, current client visits, or other local marketing programs directed by Sales management.

  • Analyzing the customer needs and interests, determining which products are appropriate and referring to appropriate party when necessary.

  • Completing and submitting accurate new business paperwork, expense reports and weekly activity reports by agreed upon dates set by Sales management.

  • Expediting the resolution of customer problems or complaints.

  • Projecting a positive image in representing the Corporation to clients and the community.

  • May be required to travel outside of geographical territory for purposes of attending Conference, training sessions and/or area Zone meetings.

Qualifications

  • H.S. Diploma - Required

  • Bachelor's Degree - Preferred

  • 5 years of experience in Outside Sales.

  • 4 years of experience in the Human Capital Management Industry.

  • Cold Calling experience.

  • Customer Relationship Management (CRM) Software experience.

  • Driver's License - Required

Compensation

In the spirit of pay transparency, we are excited to share that the compensation range for this position is typically between $75,000 - $150,000. This range includes base pay plus commissions but does not consider other components that make up the total rewards package for the position. If you are hired at Paychex, your overall compensation will be determined based on factors such as geographic location, skills, education, and/or experience which may result in total compensation outside of this range.

Live the Paychex Values

  • Act with uncompromising integrity.

  • Provide outstanding service and build trusted relationships.

  • Drive innovation in our products and services and continually improve our processes.

  • Work in partnership and support each other.

  • Be personally accountable and deliver on commitments.

  • Treat each other with respect and dignity.

What's in it for you?

  • We value your well-being: We provide over 21 comprehensive rewards, including medical coverage, virtual wellness classes, tuition reimbursement, 401(k) + employer match, adoption assistance, financial assistance, and much more.

  • We value your time: From paid time off to company holidays, culture days, and comprehensive work-life balance programs, we will ensure you have the flexibility you need to be your best.

  • We value your development: Our award-winning training and development programs empower our employees with ongoing learning opportunities to give you the building blocks to grow your career.

  • We value your perspective: Our company culture reflects the diversity of our employees. We want you to be you and your voice to be heard.

  • We value our communities: We offer paid time off for volunteerism and promote many company-wide and local initiatives that benefit organizations you care about.

Note: The benefits described apply to full-time employees. Benefits for part-time, contract, and intern roles may vary.

Not sure if you meet every requirement?

At Paychex, we know that great talent comes in many forms. If you're passionate about the role but don't check every box, we still encourage you to apply. You might be the right fit - either for this position or another opportunity with us.

Paychex is an equal opportunity employer. We are committed to fostering a respectful and inclusive workplace where all individuals are treated fairly and evaluated based on their qualifications, experience, and merit. We comply with all applicable federal, state, and local laws prohibiting discrimination in employment.

How this job compares

Set against the 2,305 open Sales Executive jobs on Olive Jobs, counted November 12, 2026.

Pay
  • This posting$75–150K/yr
  • Illinois median$111–187K/yr70 salary ranges
  • US median$122–188K/yr1,739 salary ranges

This range's midpoint, $113K, is 24% below the Illinois median midpoint ($149K) — in the middle half of Sales Executive salary ranges in Illinois.

Openings
Olive Jobs lists 82 open Sales Executive jobs in Illinois and 2,305 across the US. 10% of them nationwide are listed as remote or flexible.
Hiring the most in Illinois
Experience
This posting asks for at least 5 years of experience; Sales Executive postings that state a minimum ask for 5 years at the median (1,733 postings).
Education
This posting asks for a high school diploma; 450 of the 2,305 open Sales Executive jobs (20%) ask for a high school diploma or higher.

Pay, requirements and demand for Sales jobs

Counted across the open, public US postings on Olive Jobs on November 12, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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