Territory Sales Manager Mid-West (New)

Location: Field-based / Remote (U.S.) Employment Type: W-2, Base Salary + Commission Compensation: $60,000 Base + Commission + Residuals First-Year On-Target Earnings (OTE): $120,000 at plan Why This Is a Strong Opportunity 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 About Hourly Hourly is a fast‑growing fintech company that simplifies payroll and workers' compensation for small and mid‑sized businesses in the U.S. Our platform delivers: Payroll runs in under 30 seconds Same‑day direct deposit Seamless payroll + Workers' Comp integration Unlimited payroll runs at no extra cost Elimination of surprise Workers' Comp audits 85%+ retention when payroll and WC are sold together The Opportunity As a Territory Sales Manager , you will focus on generating new business by selling Hourly's payroll and Workers' Comp solution to small and mid‑sized businesses. This is a true hunter role . You will own your territory, generate your own pipeline, close new accounts, and build long‑term residual income through consistent performance. What You'll Do 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 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 Ready to Own Your Success? If you're a driven B2B sales professional who thrives on prospecting, closing new business, and building long‑term income through residuals — we'd love to talk. Hourly is an equal opportunity employer committed to building a diverse and inclusive team. #J-18808-Ljbffr