Hourly, Inc. is a fast-growing fintech and insurtech pioneer that simplifies payroll and workers’ compensation for small and mid-sized businesses (SMBs) across the United States. While traditional payroll and insurance systems rely on manual data entry and outdated processes, Hourly leverages a proprietary, real-time technology ecosystem to bridge the gap between labor costs and insurance premiums.
By integrating time tracking, payroll, and workers’ comp into a single, intuitive platform, Hourly enables business owners to run payroll in under 30 seconds and eliminates the stress of year-end workers’ comp audits. Hourly is transforming how the 80+ million hourly workers in America are paid and protected.
Position BackgroundSince its launch, Hourly has seen rapid adoption, particularly in high-complexity sectors such as construction, hospitality, and service industries. As we move into 2026, Hourly is expanding its footprint to meet the increasing demand for transparent, mobile-first financial tools that support both employers and employees.
The Territory Sales Manager will be a critical driver of this expansion. This is a "hunter" role designed for high-performing sales professionals who thrive in a high-activity, short-cycle environment. You will be responsible for generating new business by selling Hourly’s integrated solution directly to SMB owners and building a robust referral network of CPAs, insurance brokers, and financial advisors. This role offers a unique opportunity to build a personal book of business with uncapped commission potential and long-term residual income
Corporate StructureThis position reports directly to the Regional Sales Director.
This is a 100% remote role that requires proactive territory management. While you own your pipeline, you are supported by a dedicated Sales Enablement team, Customer Success managers, and modern CRM tools to ensure seamless onboarding and high client retention.
Key ResponsibilitiesPipeline & Territory Management
- Lead Generation: Drive consistent outbound activity to generate a 3–4x pipeline coverage through cold outreach, referrals, and local events.
- Full Sales Cycle Ownership: Manage the entire process from initial discovery and platform demos to proposal development and closing the first payroll run.
- Sales Targets: Consistently close 8+ new accounts per month to meet and exceed territorial production objectives.
Partner Relationship Development
- Referral Networks: Identify and cultivate strategic partnerships with CPAs, insurance brokers, and banks to create a steady stream of warm leads.
- Market Engagement: Actively participate in local industry trade associations and events to build the Hourly brand within your territory.
Strategic Operations
- Data Integrity: Maintain meticulous CRM hygiene and provide accurate weekly forecasting to leadership.
- Customer Success Collaboration: Work closely with the onboarding team to ensure a "white-glove" transition for new clients, focusing on 85%+ retention for integrated accounts.
- Competitive Analysis: Gather field intelligence on local competitors and market trends to inform Hourly’s go-to-market strategy.
Requirements
- Experience: 1+ years of B2B field or territory sales experience, specifically within payroll, HCM, workers’ comp, or the insurance industry.
- Education: Bachelor’s degree in Business, Marketing, or a related field (preferred).
- Skills: * Proven "hunter" mentality with a track record of exceeding new-logo quotas.
- Strong closing skills and the ability to navigate short, high-volume sales cycles.
- Excellent verbal and written communication, with a knack for presenting complex fintech solutions simply.
- Proficient with Google Workspace and modern CRM tools (Salesforce etc.).
- Attributes: Self-starter with superior organizational skills; comfortable selling to SMB owners in blue-collar and service-based industries.
Benefits
- Base Salary: $60,000
- First-Year OTE: $120,000 (Base + Commission + Residuals)
- Uncapped Upside: No commission ceilings; higher performance unlocks higher tiers.
- Health & Wellness: Medical, dental, vision, and life insurance.
- Future Planning: 401(k) retirement plan.
- Flexibility: Unlimited Time Off (PTO) and 100% remote work environment.
- Support: Communication stipend, client entertainment budget, and mileage/expense reimbursement.
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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