Remote Territory Sales Leader: Payroll & WC Residuals

Hourly; Peoria (IL); On-site; USD 54,000 - 66,000; Full time

Benefits offered by this job

Medical insurance

401(k)

Unlimited time off

100% remote

Communication stipend

Mileage reimbursement

Job summary

Hourly, a fintech company focused on payroll and workers' compensation for SMBs, is seeking a Territory Sales Manager to generate new business nationwide in the United States. You will own your pipeline, drive outbound prospecting, and close opportunities for Hourly's payroll and WC solutions.

This hunter-focused role offers a base salary plus commission and residuals, with an estimated first-year OTE of around $120,000 and fully remote work.

Qualifications

• 1+ years of B2B field or territory sales experience.
• Proven new-logo hunter with 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.
• Bachelor's degree preferred.

Responsibilities

• 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 with CPAs, insurance brokers, financial advisors, and banks.
• Forecast accurately: Maintain strong CRM hygiene, deal-stage accuracy, and weekly forecasting.
• Collaborate cross-functionally 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.

Skills

Outbound prospecting

Territory sales

Communication skills

Self-starter

Small business selling

Google Workspace

Education

Bachelor's degree preferred

Tools

CRM tools

Job description

Hourly, a fintech company focused on payroll and workers' compensation for SMBs, is seeking a Territory Sales Manager to generate new business nationwide in the United States. You will own your pipeline, drive outbound prospecting, and close opportunities for Hourly's payroll and WC solutions.

This hunter-focused role offers a base salary plus commission and residuals, with an estimated first-year OTE of around $120,000 and fully remote work.