Territory Sales Manager - Southeast Region

Hourly, Inc.
Tampa, FL

Location: Field-based / Remote (U.S.)
Employment Type: W-2, Base Salary + Commission
Compensation : $60,000 Base + Commision + Residuals
First-Year On-Target Earnings (OTE): $100,000–$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.
  • Close new business: Consistently close 4 or more new accounts per month with SMB owners.
  • 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
  • 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
Posted 2026-02-12

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