Founding Wholesale Broker - Trucking

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 UPSIDE

Target 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

1. Application review

2. A focused introductory conversation

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

4. A live placement working session using a realistic trucking risk

5. 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.