Senior Enterprise Sales Leader AI-Driven HCM Deals

Paychex; Chicago (IL); Hybrid; USD 85,000 - 200,000; Full time

Benefits offered by this job

Medical coverage

401(k) + employer match

Tuition reimbursement

Paid time off

Work-life balance programs

Job summary

Paychex is seeking an experienced Enterprise Sales professional to drive net-new business with organizations 100–5,000+ employees across defined territories in the United States. You will lead full-cycle sales from prospecting to close, building value across the One Paychex portfolio.

You’ll partner with Solutions Engineers and RevOps, manage a robust pipeline with disciplined forecasting, and advance high-impact deals through a structured, team-selling environment.

Qualifications

• H.S. Diploma - Required.
• Bachelor's Degree - Preferred.
• 5 years of experience in relevant professional sales.
• 3 years of experience in HCM industry.
• Driver's License - Required.

Responsibilities

• 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.
• Own your pipeline with rigorous forecasting, disciplined front-end prospecting, and deal control through the close.

Skills

Enterprise Sales

Sales Prospecting

Go-to-Market Strategy

Customer Relationship Management

Education

H.S. Diploma

Bachelor's Degree

Job description

Paychex is seeking an experienced Enterprise Sales professional to drive net-new business with organizations 100–5,000+ employees across defined territories in the United States. You will lead full-cycle sales from prospecting to close, building value across the One Paychex portfolio.

You’ll partner with Solutions Engineers and RevOps, manage a robust pipeline with disciplined forecasting, and advance high-impact deals through a structured, team-selling environment.