Territory Sales Manager Mid-West (New)

About the role

Build a book of business: Earn upfront commissions and long-term residual income as your client base grows
Uncapped upside: No commission ceilings — higher performance unlocks higher commission tiers
Hunter-focused role: High-activity, high-volume sales motion with short sales cycles
Strong product-market fit: Payroll and Workers' Comp are mission-critical services for SMBs
Autonomy with support: You own your pipeline and territory, backed by sales enablement, Customer Success, and modern tools

Why This Is a Strong Opportunity

Hourly is a fast-growing fintech company that simplifies payroll and workers' compensation for small and mid-sized businesses in the U.S.

What You'll Do

• Possess a healthy 3-4x pipeline coverage and drive outbound activity, referrals, events, and partner-sourced leads
• Manage the full sales cycle from first outreach to first payroll run, including discovery, demos, proposal development, and close
• Develop relationships with CPAs, insurance brokers, financial advisors, and banks to build referral partnerships
• Maintain strong CRM hygiene, deal-stage accuracy, and weekly forecasting
• Partner with Customer Success to ensure smooth onboarding and strong early retention
• Share insights from the field to inform product, messaging, and go-to-market strategy

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