THE COMPANY

Our client is a large, publicly traded provider of human capital management and business services, helping employers manage payroll, HR, benefits, retirement services, compliance, insurance, workforce management, and other employer-related solutions. The company serves a diverse SMB and mid-market customer base and operates in a highly active, field-sales-driven environment centered on new business development, customer growth, referral partnerships, and disciplined sales execution.

The organization continues to make significant investments in sales leadership as part of ongoing growth initiatives and recent strategic acquisitions. This is an opportunity to join a stable, nationally recognized platform with a strong brand, established market presence, opportunities for internal advancement, and a continued commitment to developing frontline sales leaders.

THE JOB

Our client is seeking a District Sales Manager to lead an SMB-focused outside sales team in the Chicago market. This frontline field-sales leadership role is responsible for driving new business results, coaching and developing outside sales representatives, creating accountability, and ensuring consistent execution within a high-activity sales environment.

The role is heavily focused on new logo acquisition and field execution. The ideal candidate has experience leading sales professionals in a prospecting-intensive environment and can reinforce pipeline discipline, activity expectations, referral partner development, and daily execution standards.

The District Sales Manager will spend substantial time in the field alongside sales representatives through ride-alongs, live coaching, prospecting support, pipeline reviews, and ongoing development efforts. Candidates should be comfortable working within a metrics-driven sales culture where visibility, coaching, accountability, and performance management are essential to success.

The position also requires familiarity with referral and channel-based business development ecosystems, including CPA relationships, banking partnerships, broker networks, and other local referral channels commonly associated with SMB HCM and payroll sales environments.

Based in the Chicago market, this role requires a leader who can quickly establish credibility with outside sales teams, support rep development, and drive sustained new business growth across the district.

THE QUALIFICATIONS

Must-Have Qualifications

• Experience leading outside B2B sales teams in a new-business-focused environment
• Proven success coaching, training, developing, and improving sales representative performance
• Experience managing prospecting activity, pipeline accountability, and field execution standards
• Ability to thrive within a high-accountability, metrics-driven sales culture
• Experience leading field-based or outside sales organizations
• Strong communication, coaching, and leadership capabilities
• Ability to reside in and support the Chicago market
• Willingness to spend significant time in the field conducting ride-alongs and live coaching

Strongly Preferred Qualifications

• Experience in payroll, HCM, HR technology, PEO, benefits, business services, or related industries
• Background with organizations such as ADP, Paylocity, Paycom, Paycor, UKG, TriNet, Insperity, Dayforce, Rippling, Gusto, or similar companies
• Exposure to CPA, banking, broker, referral, or partner-channel sales ecosystems
• Experience leading SMB-focused sales teams
• Participation in formal leadership development or management training programs

THE BENEFITS

• Base salary: approximately $100K–$125K
• Target bonus: approximately $50K
• RSUs/equity: approximately $15K

Additional benefits include:

• Medical
• Dental
• Vision
• FSA options
• 401(k)
• Discretionary unlimited time off
• Cell phone stipend eligibility
• Sales recognition and incentive programs