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
Top Skills
What We Do
Headquartered in Palo Alto, California, Hourly.io is an insurtech startup offering workers’ comp insurance and full-service payroll for small and medium businesses with hourly workers. Powered by real-time data, Hourly’s platform ensures running payroll is as quick as pressing a button and that you get accurate workers’ comp premiums down to the penny.
Why Work With Us
We’re a special bunch. We’re all fully remote, which makes us highly collaborative, understanding and resourceful. We share a mission to make the world a better place with a service that makes it easier for business owners to pay, insure and manage their Hourly workers.
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