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 Hourly s product is proven, sticky, and designed for SMBs - making it a strong sell for high-performing sales professionals. 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. Originally posted on Himalayas