Territory Sales Manager Mid-West (New)

Hourly, Inc.

$60K — $120K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 1+ years of B2B field or territory sales experience in relevant industries (payroll, HCM, Workers' Comp, etc.)
  • Proven new-logo hunter with a track record in outbound prospecting
  • Experience selling to small business owners, especially in the construction, restaurant, and service sectors
  • Ability to manage short sales cycles in high-volume environments
  • Strong communication skills, both written and verbal
  • Self-starter with territory planning and execution skills
  • Proficiency in Google Workspace and modern CRM tools, Bachelor's degree preferred

Responsibilities

  • Prospect and generate pipeline through various channels
  • Manage the full sales cycle from outreach to closing
  • Build referral partnerships with CPAs, brokers, and financial advisors
  • Accurately forecast sales with strong CRM upkeep
  • Collaborate with Customer Success for effective onboarding
  • Provide market feedback to improve product and strategy

Benefits

  • Medical, dental, vision, and life insurance
  • 401(k) retirement plan
  • Unlimited time off policy
  • Fully remote work opportunity
  • Communication stipend and client entertainment budget
Full Job Description
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

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.

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