District Sales Manager; SMB

District Sales Manager

Our client is hiring a District Sales Manager to lead an SMB-focused outside sales team in the Chicago market. This is a frontline field-sales leadership role responsible for driving new business performance, coaching outside sales representatives, building accountability, and helping teams consistently execute in a high-activity sales environment.

This role is highly focused on new logo acquisition and field execution. The ideal candidate understands how to lead sales professionals in a prospecting-heavy environment while reinforcing pipeline discipline, activity expectations, referral partner development, and day-to-day execution standards.

The District Sales Manager will spend meaningful time in the field with sales representatives through ride‑alongs, live coaching, prospecting support, pipeline reviews, and ongoing rep development. Candidates should be comfortable operating within a metrics‑driven sales culture where leadership visibility, coaching intensity, and accountability are critical to success.

This role also requires strong exposure to referral and channel‑driven business development ecosystems, including CPA relationships, bank partnerships, broker networks, and other local business referral channels commonly associated with SMB HCM/payroll sales environments.

The position is market‑based within the Chicago area and requires a leader who can build credibility quickly 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
• Demonstrated success coaching, training, developing, and improving sales rep performance
• Experience managing prospecting activity, pipeline accountability, and field execution standards
• Ability to operate within a high‑accountability, metrics‑driven sales culture
• Experience leading field‑based or outside sales organizations
• Strong communication, coaching, and leadership skills
• Ability to live in and support the Chicago market
• Willingness to spend significant time in the field with reps through ride‑alongs and live coaching

Strongly Preferred Qualifications

• Payroll, HCM, HR technology, PEO, benefits, business services, or related industry experience
• Experience with in organizations such as ADP, Paylocity, Paycom, Paycor, UKG, Tri Net, Insperity, Dayforce, Rippling, Gusto, or similar environments
• Exposure to CPA, bank, broker, referral, or partner‑channel sales ecosystems
• Experience leading SMB‑focused sales teams
• Prior participation in formal leadership development or management training programs

• 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 opportunities