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About Breakwater Markets LLC
Breakwater Markets LLC is a specialty wholesale insurance brokerage platform focused on commercial transportation risk. As a standalone subsidiary within the Cover Whale ecosystem, Breakwater is designed to place business that falls outside traditional delegated authority programs, leveraging a broad network of carrier relationships across admitted and E&S markets.
Position Summary
Breakwater Markets is seeking a results-driven Vice President of Wholesale Brokerage to
play a foundational role in building and scaling its transportation-focused wholesale platform.
This is a senior leadership role with direct impact on production, portfolio quality, and carrier partnerships. The VP will be responsible for developing and executing a wholesale brokerage strategy that drives profitable growth, deepens carrier relationships, and expands our market presence nationwide.
This role reports to senior leadership and will work cross-functionally with underwriting, operations, and actuarial teams to ensure our wholesale business operates with discipline, efficiency, and a long-term growth orientation.
Key Responsibilities
Carrier Relations

• Develop, manage, and grow strategic relationships with carriers active in the commercial trucking space.
• Secure and manage brokerage appointments and placement relationships with key carrier partners across admitted and E&S markets.
• Serve as the primary point of contact for carrier partners; proactively communicate on portfolio performance, market conditions, and growth initiatives.
• Monitor carrier appetite shifts and adjusting distribution strategy accordingly.

Production & Distribution

• Own wholesale production targets and lead efforts to grow gross written premium through broker channels.
• Build and maintain a network of producers in the commercial trucking segment.
• Develop and execute go-to-market strategies for new product launches and geographic expansion.
• Identify and pursue new distribution opportunities, market segments, and strategic partnerships.
• Track production pipeline, submission activity, and bind ratios; report regularly to leadership on performance vs. targets.Provide market intelligence and competitive insights to inform product development and pricing decisions.
• Represent Breakwater Markets at industry events, conferences, and association meetings relevant to commercial trucking and wholesale distribution.

Requirements
Required

• 8+ years of experience in commercial trucking insurance, with a strong background in wholesale brokerage, MGA, or carrier distribution.
• Demonstrated track record of building and managing carrier relationships and growing production in a wholesale or MGA environment.
• Deep knowledge of commercial auto and trucking insurance products, market dynamics, and regulatory landscape.
• Existing relationships with carriers active in the commercial trucking space strongly preferred.
• Strong analytical skills with the ability to interpret loss data, production metrics, and market trends.
• Exceptional communication and relationship management skills; able to influence at the executive level internally and externally.
• Active P&C insurance license (or ability to obtain promptly upon hire).

Preferred

• Experience at an MGA, program administrator, or specialty insurer focused on commercial transportation.
• Bachelor's degree in business, finance, risk management, or a related field; advanced degree or professional designations (CPCU, CIC, ARM) a plus.

Benefits
Breakwater Markets LLC offers a competitive total rewards package designed to attract and retain top talent in the specialty insurance market.

• Base Salarycommensurate with experience and qualifications.
• Annual Performance Bonus: Tied to individual and company performance targets.
• Health, dental, and vision insurance.
• 401(k) with company contribution.
• Flexible, remote-first work environment.
• Professional development support including licensing, designations, and industry conference participation.