Founding Wholesale Broker - Trucking

Hedgespecialty; San Francisco (CA); Hybrid; USD 125,000 - 250,000; Full time

Benefits offered by this job

Health benefits

Equity grant

Performance equity up to 0.25%

Job summary

Hedge is hiring a founding wholesale broker to build and own our trucking practice from the ground up. You will blend retail-agency relationships, market judgment, and placement craft to generate durable revenue across trucking and transportation risks, working closely with founders and underwriters.

The role offers substantial upside, including a base salary, generous OTE, and equity in a San Francisco-based team. You will be in a highly dynamic, high-growth environment with direct impact.

Qualifications

• At least 3 years of brokerage, underwriting, or closely related trucking experience.
• Strong network and sharp market judgment.
• Operating discipline to manage details without losing momentum.

Responsibilities

• Build a focused retail-agency pipeline in trucking.
• Qualify risks, shape submissions, and select markets for opportunities.
• Negotiate terms, explain tradeoffs, and drive placements from intake through bind.

Skills

Brokerage experience (trucking)

Underwriting experience

Market judgment

Relationship building

Job description

Build the function, not just the task list.

The playbook is still being written. You will make decisions that become the standard for the people hired after you.

01 / OWNERSHIP

Build the function, not just the task list.

The playbook is still being written. You will make decisions that become the standard for the people hired after you.

Own real outcomes

02 / CRAFT

Learn insurance from the inside.

Work directly with founders, brokers, underwriters, and markets on the difficult commercial risks where judgment matters.

Build durable expertise

03 / UPSIDE

Exceptional performance should feel exceptional.

High target earnings, uncapped accelerators on quota roles, and meaningful equity align what you create with what you earn.

Earn with impact

Founding Wholesale Broker - Trucking

Employment Type

Full time

Location Type

On-site

Department

Brokerage

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.

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.