Territory Sales Manager – Mid-West

Hourly

Territory Sales Manager focusing on generating new business for payroll and Workers’ Comp solutions. Selling to small and mid-sized businesses with a focus on long-term relationships.

Posted 7/6/2026full-timeRemote • Illinois, Minnesota, Missouri, Ohio, Wisconsin • 🇺🇸 United StatesJunior💰 $60,000 per yearWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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

Comp & perks

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

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Sales Cycle ManagementPipeline GenerationForecastingProposal DevelopmentMarket Feedback Analysis

Soft Skills

Strong Communication SkillsSelf-Starter MindsetCollaboration