# Founding Wholesale Broker - Trucking at Hedge Specialty

Founding Wholesale Broker - Trucking at Hedge Specialty in San Francisco - In Office. On-site, full-time, paying $125k–$250k. Posted August 27, 2026.

- Company: Hedge Specialty
- Location: San Francisco - In Office
- Workplace: On-site
- Job type: Full-time
- Pay: $125k–$250k
- Posted: 2026-08-27
- Apply: https://jobs.ashbyhq.com/hedge/c4df26b3-d27c-41bf-9bbe-fa60004e8da0/application
- Source: https://jobmagic.ai/jobs/founding-wholesale-broker-trucking-hedge-specialty-bt8h7y

## Description

### **THE OPPORTUNITY**

Hedge is hiring a founding wholesale broker to build and own our trucking practice. You will combine retail-agency relationships, market judgment, placement craft, and relentless follow-through to produce durable revenue in trucking, motor carrier, and transportation risks.
 

### **COMPENSATION AND UPSIDETarget OTE is $500K. Base salary is $125K-$250K, creating a target cash range of $475K-$600K across the base range. Target variable compensation is $350K at $5M in annual new bound premium, with uncapped accelerators above target. Equity is 0.50% at hire, with up to an additional 0.25% performance grant.**
 

### **WHAT YOU WILL OWN**

- Build a focused retail-agency pipeline in trucking

- Qualify risks, shape submissions, and select the right markets for each opportunity

- Negotiate terms, explain tradeoffs, and drive placements from intake through bind

- Develop strong working relationships with underwriters and program markets

- Maintain disciplined pipeline, renewal, and revenue forecasting

- Turn placement knowledge into repeatable playbooks and product feedback

 

### **WHAT SUCCESS LOOKS LIKE**

- **First 30 days:** master Hedge's market access, appetite, workflow, and current opportunity set

- **By day 60:** own a credible agency and submission pipeline with clear placement strategies

- **By day 90:** bind initial business and demonstrate repeatable conversion

- **In 12 months:** build a high-quality trucking book and bind $5M in annual new premium

 

### **WHO THRIVES HERE**

You have at least three years of brokerage, underwriting, or closely related experience in trucking. You have a strong network, sharp market judgment, and the operating discipline to manage details without losing commercial momentum.
 

### **WHY HEDGE**

Hedge is building the operating system for commercial insurance distribution. You will work directly with the founders, own a consequential part of the company, and help define how the function works as we scale. We offer health benefits and meaningful equity.
 

### **WORK MODEL**

This role is based in San Francisco and works in person with the team six days a week.
 

### **INTERVIEW PROCESS**

- Application review

- A focused introductory conversation

- A production, book, and market-relationship deep dive

- A live placement working session using a realistic trucking risk

- Final conversation with the founders

Hedge is an equal opportunity employer. We evaluate candidates based on ability, judgment, and potential, and we do not discriminate based on protected characteristics.