Job Description

Locations: Chicago, Illinois

Categories: Sales

Position Type: Full Time

Company: ['Paychex']

Req ID: 46670

Imagine Your Future with Us! Since 1971, Paychex has been at the forefront of simplifying HR, payroll, and benefits for American businesses. Our digital HR technology and advisory solutions cater to the changing needs of employers and their employees. With our award-winning training and endless opportunities for growth and development, you can build a lifelong career with us. We pride ourselves on fostering an inclusive and innovative culture. Our leaders are here to support your career journey; they and our dedicated employees embody the values that drive us to support each other, our clients, and our communities. Join us to pursue your passion and unleash your potential.

Overview

Where Growth Gets Strategic - and Your Career Does Too

Mid-Market Sales is where experience meets impact. You’ll partner with growing businesses (20–99 employees), navigating the complexity of expansion—helping them strengthen their people operations and scale with confidence.

This is a consultative, relationship-driven environment where you’re not just closing deals—you’re solving real business challenges. Every conversation builds insight, every deal sharpens your expertise, and every win positions you as a trusted advisor to business owners.

Responsibilities

What You’ll Do

• Drive new business by prospecting and winning new logos within your assigned territory
• Sell a robust suite of solutions, including Paychex Flex® and advanced HR services.
• Execute consistent outbound activity (calls, outreach, networking, partnerships, and follow-ups) to build a pipeline
• Lead consultative sales conversations with business owners and key decision-makers
• Manage a high velocity sales process with small and mid-size businesses (1-2 call closes)
• Own the full sales process—from discovery and solutioning to closing

What It Takes to Win

• 2-5 years professional sales experience; 3 years B2B Sales Environment
• 2+ years HCM experience strongly preferred
• Ability to navigate consultative, solution-based sales conversations
• Strong prospecting mindset with comfort driving outbound, in-person field activity
• Resilience, accountability, and a results-driven approach
• Coachability with a desire to continuously improve and grow

Why This Role

• Unlimited earning potential with performance-based incentives
• More complex, higher-value deals that accelerate your sales expertise
• Opportunity to become a trusted advisor to growing businesses
• Clear path to advance your career in a fast-paced, growth-focused environment with clear pathways to the next step in your career

If you’re ready to elevate your sales career while helping businesses scale, this is where you grow next.

Qualifications

• H.S. Diploma - Required
• Bachelor's Degree - Preferred
• 2 years of experience in B2B Sales/Marketing.
• 2 years of experience in Human Capital Management (HCM) industry.
• Cold Calling experience.
• Customer Relationship Management (CRM) Software experience.
• Valid Driver's License - Required

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.