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Sr Sales Executive, Enterprise

Location
Chicago, IL
Work type
Full Time
Posted
2026-08-03

Job description

Responsibilities

What You’ll Do

Hunt and close net-new enterprise business with organizations 100 to 5,000+ employees across defined territories
Run disciplined full-cycle sales from executive-level prospecting through multi-stakeholder discovery, demo, and close
Build high-value solution bundles or standalone solutions across the full One Paychex Portfolio, including PEO, HR Solutions, Managed Payroll, Benefits, Retirement, Merchant Services, and more, while earning accelerators on every module you attach.
Partner with Solutions Engineers, RevOps, and a world-class channel ecosystem, including 700+ active broker relationships and financial services firms in a GTM team-selling environment, so you are never building alone.
Own your pipeline with rigorous forecasting, disciplined front-end prospecting, and deal control through the close.
What It Takes to Win

5+ years of quota-carrying experience or complex B2B sales with a verifiable track record of hunting, building a pipeline, and closing
Proven ability to engage economic buyers at the C-level and navigate multi-stakeholder engagement
Experience selling into organizations of 100+ employees
High accountability, resilience, and ownership of results because this team sets high expectations and meets them
Why This Role

Unlimited earning potential tied to performance and results with a focus on career development
World-Class Club Experiences for Top Performers
Access to larger, more strategic deals with real business impact
More ways to win! We offer a broad portfolio of products and services beyond tech to increase deal size
An AI-Powered Platform That Closes Deals Faster
A Commission Plan Engineered for Top Performers

This Role Is for You If…

You have been closing at a high level, and you are ready for a bigger stage. You want a platform you can believe in, a comp plan that actually rewards your performance, and leaders who will develop you rather than just measure you. You want to be part of something still being built, where the work you put in this year shapes what this enterprise organization looks like in three.

Qualifications

H.S. Diploma – Required
Bachelor’s Degree – Preferred
7 years of experience in relevant professional sales.
5 years of experience in HCM industry.
Experience carrying a sales quota.
CORE HCM provider experience.
Experience working with mid-size businesses or larger.
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 $85,000 – $200,000. 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.

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