Head of Sales

Harper•San Francisco, CA

3d•Hybrid

About The Position

The company is scaling to $10M in monthly premium sold by Q1 2026 and needs someone to build the sales machine to achieve this. The role involves architecting the entire sales function, building a lean team of elite producers supported by embedded engineering to write hundreds of millions in premium. The goal is to achieve the size and scale of industry giants like Marsh, Gallagher, and Brown, with a focus on 10x efficiency compared to traditional brokerages. The position is about building what comes next, not just managing what exists.

Requirements

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

Nice To Haves

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
Can recruit anyone and turn them into a top performer
Builds systems that scale, not just processes that work today
Obsessed with performance and comfortable giving direct feedback
Gets excited about using AI to eliminate busywork (not relationships)
Thrives in chaos and builds order without killing speed
Wants to get rich alongside the people they develop

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