Welcome to Hourly! We make payroll and workers comp super-duper simple.
Territory Sales Manager Mid-West (New)
Location
Illinois
Posted
21 days ago
Salary
Not specified
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
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.
Job 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.
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