Head of Sales jobs in United States
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Harper (YC W25) · 5 months ago

Head of Sales

Harper is a rapidly growing company in the commercial insurance sector, seeking a Head of Sales to architect their sales function and scale their operations significantly. The role involves recruiting top talent, building scalable playbooks, managing performance, and leveraging technology to create a high-efficiency sales machine.

Artificial Intelligence (AI)FinTechInsurance

Responsibilities

Recruiting & hiring top talent from insurance, tech sales, and finance
Building scalable playbooks that work across different producer backgrounds
Performance management - reviewing calls, coaching, driving consistent execution
Compensation design that attracts and retains A-players
Deal intervention - stepping in to save deals and close when needed
Carrier relationships - managing E&S wholesale brokers and direct appointments
Technology partnership - working directly with embedded engineering to build AI tools that make us unstoppable

Qualification

Commercial insurance salesBuilding P&C producer teamsScaling sales operationsCarrier relationshipsPerformance managementRecruiting talentCompensation designDeal interventionTechnology partnershipAI tools development

Required

5+ years crushing it in commercial insurance sales yourself
3+ years building and managing P&C producer teams
Deep expertise in both admitted and E&S markets
Proven track record scaling sales operations from early stage
Can close deals - you're the person we call when a big deal is going sideways
Ability to travel for work to see clients and oversee teams at various office locations

Preferred

Scaled a producer team at a brokerage, MGA, or carrier
Built an independent agency from the ground up
Led sales at a high-growth insurance company
Managed both wholesale and retail distribution channels

Benefits

Premium healthcare (90% covered)
Meals covered while at work
Development budget
Flexible PTO

Company

Harper (YC W25)

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Harper is a commercial E&S insurance brokerage.

Funding

Current Stage
Early Stage
Total Funding
$0.5M
Key Investors
Y Combinator
2025-03-12Pre Seed· $0.5M
Company data provided by crunchbase