Sales Representative Mid-West (New)

• 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 Sales Representative, 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