Vice President of Wholesale Brokerage

Cover Whale Insurance Solutions

1d•Hybrid

About The Position

Breakwater Markets is a specialized wholesale brokerage focused on delivering innovative insurance solutions in the commercial trucking and transportation sector. We partner with retail agents and carriers to create efficient market access, strong underwriting relationships, and scalable production capabilities. We are seeking a Vice President of Wholesale Brokerage to lead and scale our carrier relationships and production strategy within the commercial trucking space. This is a senior leadership role responsible for driving revenue growth, deepening market partnerships, and building a high-performing brokerage platform. This individual will operate at the intersection of distribution and underwriting—owning both top-line production and the strength of our carrier network.

Requirements

10+ years of experience in wholesale brokerage, underwriting, or carrier-side roles within commercial trucking or transportation insurance
Proven track record of production and/or carrier relationship management
Strong existing network of carrier and broker relationships in the trucking space
Demonstrated ability to negotiate and structure deals
Highly entrepreneurial with a bias toward action and results

Nice To Haves

Experience building or scaling a brokerage platform or book of business preferred

Responsibilities

Develop and own strategic relationships with insurance carriers, MGAs, and program administrators in the trucking and transportation space
Negotiate capacity, underwriting authority, and competitive terms
Expand Breakwater’s market access and diversify carrier panel
Serve as the primary escalation point for carrier-related issues
Drive wholesale brokerage production across retail agent partners
Build and execute a scalable growth strategy focused on commercial trucking risks
Identify new distribution opportunities and revenue channels
Monitor pipeline, conversion, and performance metrics
Hire, mentor, and lead a team of brokers and production staff (as applicable)
Establish best practices for submissions, placement, and client service
Partner cross-functionally with underwriting, operations, and leadership teams
Help define long-term strategy and operational infrastructure
Maintain deep knowledge of the commercial trucking insurance market, including pricing trends, capacity shifts, and regulatory dynamics
Advise internal stakeholders and clients on market conditions and strategy