PEO Director of Sales

Our client is seeking an experienced Director of Sales to lead growth efforts within its Professional Employer Organization (PEO) business throughout the Midwestern United States.

This is a hands-on sales leadership opportunity for someone who understands the PEO landscape and knows how to build, coach, and develop successful sales professionals. The Director of Sales will be responsible for driving regional growth, strengthening pipeline development, supporting sellers throughout the sales process, and creating a culture of accountability and consistent execution.

The position will focus on the Midwest, with a strong preference for candidates located in Ohio, Indiana, Nebraska, or Missouri.

The ideal candidate combines strong sales leadership with a deep understanding of consultative B2B selling and is comfortable getting directly involved in prospect strategy, complex opportunities, and the continued development of the sales team.

What You'll Do

• Lead regional sales strategy and execution for the PEO business
• Establish sales goals, growth priorities, activity expectations, and individual performance objectives
• Coach and develop Business Development Executives and other sales professionals throughout the full sales cycle
• Hold the sales team accountable for prospecting activity, pipeline development, CRM discipline, opportunity progression, and revenue goals
• Conduct regular pipeline reviews, opportunity strategy sessions, and individual coaching
• Help sales professionals strengthen prospecting, discovery, presentation, negotiation, and closing skills
• Participate in prospect meetings and complex or high-value sales opportunities when appropriate
• Identify opportunities to improve sales performance and remove barriers to growth
• Recruit, onboard, mentor, and develop new sales talent
• Support new sellers in building territories, referral relationships, centers of influence, and sustainable pipelines
• Analyze sales activity, pipeline health, conversion, win/loss trends, and overall performance
• Develop and maintain relationships with strategic partners, referral sources, and centers of influence
• Collaborate across PEO services, including HR, payroll, employee benefits, risk management, and related workforce solutions
• Partner with marketing, operations, sales enablement, and senior leadership to execute regional growth initiatives
• Reinforce a high-performance culture centered around accountability, collaboration, and consistent growth

What We're Looking For

• 5+ years of sales leadership experience; 7+ years preferred
• Strong PEO industry and sales experience
• Located in or well-positioned to lead business development throughout the Midwestern United States
• Strong preference for candidates based in Ohio, Indiana, Nebraska, or Missouri
• Proven experience coaching and developing successful B2B sales professionals
• Demonstrated success driving new business growth and managing sales performance
• Strong understanding of pipeline management, forecasting, CRM utilization, and sales metrics
• Experience supporting complex, consultative B2B sales cycles
• Ability to coach sellers while also becoming directly involved in strategic opportunities when needed
• Strong leadership, communication, presentation, and relationship-building skills
• Experience recruiting and onboarding sales professionals
• Ability to develop relationships with business owners, executives, referral partners, and other key decision-makers
• Strong understanding of the small and mid-sized business marketplace

Why Consider This Opportunity?

• Take a leadership role in the continued growth of an established PEO business
• Lead and develop a team of consultative B2B sales professionals
• Represent a comprehensive PEO solution supporting clients across HR, payroll, employee benefits, risk management, and workforce needs
• Leverage an established network of internal partners and referral opportunities
• Play an active role in sales strategy, talent development, and regional expansion
• Join a collaborative organization with significant resources supporting continued growth

If you're an experienced PEO sales leader who enjoys developing people, building high-performing sales teams, and driving measurable growth, we'd love to connect.