Hedge Opens 16 Founding Roles to Build an AI-Native Specialty Insurer
San Francisco startup Hedge has opened 16 founding positions across engineering, underwriting, sales, and specialized wholesale brokerage lines. Founded in 2026 and backed by Y Combinator as part of its P26 batch, the company is assembling an in-person core team to build what it describes as an AI-native specialty insurance company.
While Hedge lists an initial team size of two people, its hiring plan covers vertical commercial lines spanning trucking, medical malpractice, cyber, entertainment, and commercial auto.
Automated Systems and Insurance Roots
Hedge is led by co-founders Luke Button and Luke Rosa, both of whom bring backgrounds from operational tech startups and insurance.
Button serves as CEO. He previously founded Fernstone, an AI-powered retail insurance brokerage that raised $500,000 in seed capital and participated in Y Combinator’s F25 batch. Before that, Button led a growth team at Traba, worked as Head of Growth at Antimetal, and co-founded Contrast, which was acquired. He holds a bachelor’s degree in philosophy from St. John's University.
Rosa previously worked as Head of Scaled Systems at Traba, a Series A company backed by Founders Fund and Khosla Ventures. In that role, he "replaced humans with AI agents to manage $20 MM+ in revenue." Rosa studied economics at the University of Chicago.
Building Across Specialty Lines
Specialty insurance typically covers high-complexity, non-standard risks that traditional automated policy forms bypass. Hedge’s hiring points to a strategy that pairs machine systems with specialized domain coverage.
The company is recruiting specialized brokers for specific risk categories, including the Founding Wholesale Broker - Entertainment and the Founding Wholesale Broker - Medical Malpractice. The brokerage postings also cover commercial auto, property, casualty and excess, trucking, and professional lines.
On the technical and underwriting side, Hedge is hiring a Founding Engineer to lead product development and a Founding Underwriter to structure policy risk. Fourteen of the sixteen open roles are based on-site in San Francisco, while two senior executive roles are open to remote candidates across the United States.
Open Roles at Hedge
All salaries below reflect the exact ranges provided by the company.
| Role | Location | Work Mode | Salary |
|---|---|---|---|
| Founding Engineer | San Francisco - In Office | Onsite | $150,000 – $250,000 USD / year |
| Founding Underwriter | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Entertainment | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Medical Malpractice | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Commercial Auto | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Property | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Casualty and Excess | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Professional Lines, Management Liability, and Cyber | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Wholesale Broker - Trucking | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |
| Founding Head of Partnerships | Remote (US) | Remote | $120,000 – $250,000 USD / year |
| Founding Head of Markets | Remote (US) | Remote | $125,000 – $200,000 USD / year |
| Founding Account Executive | San Francisco - In Office | Onsite | $110,000 – $150,000 USD / year |
| Founding Growth Operations | San Francisco - In Office | Onsite | $110,000 – $150,000 USD / year |
| Business Development Representative | San Francisco - In Office | Onsite | $60,000 – $100,000 USD / year |
| Founding Sales Development Representative (SDR) | San Francisco - In Office | Onsite | $60,000 – $100,000 USD / year |
| General Application | San Francisco - In Office | Onsite | $125,000 – $250,000 USD / year |