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Territory Sales Manager – Mid-West

Outside SalesSalesFull TimeRemoteTeam 51-200H1B No SponsorCompany SiteLinkedIn

Location

Illinois + 4 moreAll locations: Illinois, Ohio, Michigan, Minnesota, Wisconsin

Posted

20 days ago

Salary

$60K / year

Bachelor Degree1 yr expExperience acceptedEnglish

Job Description

• Prospect and generate pipeline: Drive outbound activity, referrals, events, and partner-sourced leads; maintain a healthy 3–4x pipeline coverage. • Manage the full sales cycle: From first outreach to first payroll run, including discovery, demos, proposal development, and close. • Build referral partnerships: Develop relationships with CPAs, insurance brokers, financial advisors, and banks. • Forecast accurately: Maintain strong CRM hygiene, deal-stage accuracy, and weekly forecasting. • Collaborate cross-functionally: Partner with Customer Success to ensure smooth onboarding and strong early retention. • Provide market feedback: Share insights from the field to inform product, messaging, and go-to-market strategy.

Job Requirements

  • 1+ years of B2B field or territory sales experience, ideally in:
  • Payroll, HCM, Workers’ Comp, insurance, uniforms, food service, or SMB-focused industries
  • Proven new-logo hunter with consistent outbound prospecting experience
  • Comfort selling to small business owners, especially in construction, restaurant, and service industries
  • Experience managing short sales cycles in high-volume environments
  • Strong written and verbal communication skills
  • Self-starter mindset with the ability to plan and execute within a territory
  • Proficiency with Google Workspace and modern CRM tools
  • Bachelor’s degree preferred

Benefits

  • Medical, dental, vision, and life insurance
  • 401(k)
  • Unlimited time off
  • 100% remote
  • Communication stipend, client entertainment budget, mileage and expense reimbursement

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