Hourly
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Territory Sales Manager – Mid-West
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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