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

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in B2B sales, particularly in managing the full sales cycle from prospecting to closing. Proficient in building referral partnerships and maintaining accurate forecasting through effective CRM management.

Highest-signal resume keywords

B2B Field Sales ExperienceOutbound ProspectingCRM ProficiencySales Cycle ManagementReferral Partnership Development

ATS Keywords

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Applicant Tracking System Keywords

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

Hard Skills

Sales Cycle ManagementPipeline GenerationForecastingProposal DevelopmentMarket Feedback Analysis

Soft Skills

Strong Communication SkillsSelf-Starter MindsetCollaboration

Tools & Technologies

Google WorkspaceCRM Tools

Industry Keywords

PayrollHCMWorkers’ CompInsuranceSMB-Focused Industries

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