Territory Sales Manager Mid-West (New)
Hourly, Peoria, IL, United States
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
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
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.
#J-18808-Ljbffr
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
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
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.
#J-18808-Ljbffr