Mid-Market Sales Consultant

Paychex · Chicago

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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.

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.

• 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.

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.

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