District Sales Manager (SMB)

District Sales Manager

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.
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.
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