Territory Sales Manager – Mid-West

This is a fully remote position, open to applicants in Illinois, +4 more states.

📋 Description

• Identify and cultivate leads: Initiate outbound efforts, referrals, events, and partner-sourced opportunities; maintain a robust 3–4x pipeline coverage.

• Oversee the complete sales process: From initial outreach to the first payroll run, encompassing discovery, demonstrations, proposal creation, and closing.

• Establish referral partnerships: Forge connections with CPAs, insurance brokers, financial advisors, and banking institutions.

• Accurately predict outcomes: Ensure strong CRM practices, deal-stage precision, and weekly forecasting.

• Collaborate across departments: Work alongside Customer Success to facilitate seamless onboarding and enhance early retention rates.

• Deliver market insights: Provide field feedback to guide product development, messaging, and go-to-market strategies.

⛳️ Requirements

• Minimum of 1 year of B2B field or territory sales experience, preferably in:

• Payroll, HCM, Workers’ Comp, insurance, uniforms, food service, or SMB-centric sectors.

• Demonstrated ability to secure new clients with a consistent track record in outbound prospecting.

• Comfort in selling to small business owners, particularly within construction, restaurant, and service sectors.

• Experience managing short sales cycles in high-volume settings.

• Excellent written and verbal communication abilities.

• Self-motivated with the capability to strategize and execute within a designated territory.

• Proficient in Google Workspace and contemporary CRM software.

• Bachelor’s degree is preferred.

🏝️ Benefits

• Medical, dental, vision, and life insurance.

• 401(k) retirement plan.

• Unlimited time off policy.

• Fully remote work environment.

• Stipend for communication expenses, a budget for client entertainment, and reimbursement for mileage and other expenses.