Senior Enterprise Sales Leader — AI-Driven HCM Platform

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

Benefits offered by this job

Medical coverage

401(k) + employer match

Tuition reimbursement

Adoption assistance

Paid time off

Job summary

Paychex is seeking an experienced Enterprise Sales professional to drive net-new business with organizations ranging from 100 to 5,000+ employees. You will lead full-cycle sales from executive-level prospecting to discovery, demos, and closing, building solution bundles across the Paychex portfolio.

You will engage economic buyers at the C-level, manage a disciplined forecast, and partner with a broad ecosystem including 700+ broker relationships to maximize impact and revenue growth.

Qualifications

• 5+ years of quota-carrying sales experience or complex B2B sales with a verifiable track record of hunting, building a pipeline, and closing.
• Experience engaging economic buyers at the C-level and navigating multi-stakeholder engagement.
• Experience selling into organizations of 100+ employees.
• High accountability, resilience, and ownership of results.

Responsibilities

• Hunt and close net-new enterprise business within defined territories (100 to 5,000+ employees).
• Run full-cycle sales from prospecting through discovery, demo, and close.
• Build value bundles across the One Paychex Portfolio (PEO, HR, Payroll, Benefits, Retirement, etc.).
• Partner with Solutions Engineers and a vast broker network to enable deal closure.

Skills

Quota-carrying sales

Enterprise sales

C-level engagement

Pipeline development

Forecasting

Education

HS Diploma - Required

Bachelor's Degree - Preferred

Tools

CRM software

Job description

Paychex is seeking an experienced Enterprise Sales professional to drive net-new business with organizations ranging from 100 to 5,000+ employees. You will lead full-cycle sales from executive-level prospecting to discovery, demos, and closing, building solution bundles across the Paychex portfolio.

You will engage economic buyers at the C-level, manage a disciplined forecast, and partner with a broad ecosystem including 700+ broker relationships to maximize impact and revenue growth.