Territory Sales Manager Mid-West (New)

Hourly, Inc.; United States; Hybrid; USD 54,000 - 66,000; Full time

Benefits offered by this job

Remote work

Health benefits

401(k)

Unlimited time off

Stipend for expenses

Job summary

Hourly, Inc. is a fast-growing fintech company providing payroll and Workers’ Comp solutions to U.S. SMBs. This field-based/remote role offers a base of $60,000 plus commission and residuals, with first-year on-target earnings of about $120,000.

You will generate pipeline, manage full sales cycles, and build partnerships with CPAs, banks, and advisors, while collaborating with Customer Success to ensure smooth onboarding and strong early retention.

Qualifications

• 1+ years of B2B field or territory sales experience.
• Proven new-logo hunter with outbound prospecting.
• Experience selling to small business owners in construction, restaurant, and service industries.
• Experience with short sales cycles in high-volume environments.
• Proficiency with Google Workspace and CRM tools.

Responsibilities

• Prospect and generate pipeline with 3–4x coverage.
• Manage the full sales cycle from outreach to payroll run.
• Build referral partnerships with CPAs, brokers, advisors, and banks.
• Forecast accurately using CRM and deal-stage updates.
• Collaborate with Customer Success for onboarding and retention.
• Provide market feedback to inform product and GTM strategy.

Skills

B2B sales experience

Hunter mentality

CRM proficiency

Communication skills

Self-starter

Education

Bachelor’s degree preferred

Tools

Google Workspace

CRM tools

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

Overview

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, elimination of surprise audits, and strong retention when payroll and WC are sold together.

The Opportunity

Territory Sales Manager role focused 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 where you own your territory, generate 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.

Qualifications

• 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.