Territory Sales Manager Mid-West

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

• 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

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

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.

• 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

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.