Future AI Founder

AI Founder, Generalist – Harper (YC W25)

Base Pay Range : $100,000 – $140,000 per year.

Equity : 0.01% – 0.20% | Location : San Francisco (in‑office)

Problem

36 million businesses in America require insurance. Current regulations and contracts make it mandatory, yet most are underinsured or uninsured. The industry is slow, opaque, and confusing; over 90% of commercial insurance distribution remains human‑led.

The Thesis

When a distribution system becomes computational, efficiency drives expansion, not contraction. By making coverage fast and frictionless, we can bring the 77% of underinsured businesses into the market, creating a healthier economy and expanding the vendor ecosystem.

The Role

This position is a founder‑training apprenticeship, not an analyst role or internship. You will spend 6‑18 months embedded across sales, customer service, underwriting, and carrier relations to understand, document, and automate the entire insurance workflow.

Learning by Doing

• Take sales calls and learn how businesses buy insurance.
• Process applications to discover what carriers actually need.
• Handle customer service to identify friction points.
• Work with underwriters to grasp risk evaluation.

Building Systems

• Document every process, decision, and edge case.
• Create templates that convert tribal knowledge into structured data.
• Design scalable workflows.
• Collaborate with engineering to build automation on top of learned insights.

Three Tracks

Business Development Track – First point of contact with customers; shape their experience and inform AI handling of initial conversations.

Sales Track – Own the revenue engine; develop playbooks for prospecting, quoting, negotiating, and closing; help design AI systems that replicate the process at scale.

Customer Service Track – Master operational complexity (policy changes, certificates, claims, carrier coordination); build the knowledge base and workflows that enable AI to handle thousands of customers.

You Might Be a Fit If …

• You’re early in your career but already exceptional—recent graduate or 0‑2 years of experience with standout achievements.
• You have founder DNA—have started something or consistently build things without waiting for permission.
• You’re willing to go deep before going wide, mastering details to abstract them later.
• You recognize patterns others miss, spotting inefficiencies and thinking about fixes.
• You want to compress your career—work hard to gain five years’ worth of experience in months.

Where This Leads

• AI Operations Leadership – Run teams that manage AI systems.
• Product Management – Shape what we build based on your insights.
• Strategic Operations – Own business functions end‑to‑end.
• Founder Track – Start your own venture with deep operational experience.

Compensation

Salary: $100,000 – $140,000; Equity: 0.01% – 0.20%; Location: San Francisco, in‑office.

The Process

• 15‑minute founder call – Align on mission and pace.
• Case study / problem‑solving exercise – Show how you think.
• On‑site day – Meet the team and see the operation.

To Apply

We’re building a vertically integrated AI platform that unites go‑to‑market, sales operations, customer service, and retention. If you want to compress years of learning into months, work alongside founders, and help build something never before seen, send your resume and a few sentences on why Harper.

Application Timeline

We offer within 1–2 weeks for the right person.