Territory Sales Manager - Payroll (Other locations) at Hourly · Medley

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.

  • 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

• 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.