Cover Whale

Vice President of Wholesale Brokerage

Cover Whale  •  United States (Remote)  •  2 days ago
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Job Description

Vice President, Wholesale Brokerage
Breakwater Markets LLC
Full-Time | [Location flexible / Hybrid or Remote]

About Breakwater Markets
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.

The Role
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.

Key Responsibilities

Carrier & Market Management

  • 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 the carrier panel
  • Serve as the primary escalation point for carrier-related issues

Production & Revenue Growth

  • 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

Leadership & Platform Buildout

  • 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

Market Expertise

  • 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

What Success Looks Like

  • Expanded and diversified carrier panel with strong, durable relationships
  • Consistent growth in production and revenue
  • Scalable brokerage processes and infrastructure
  • Strong reputation in the trucking insurance market

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
  • Experience building or scaling a brokerage platform or book of business preferred
  • Highly entrepreneurial with a bias toward action and results

Benefits

Compensation

  • Competitive base salary + performance-based bonus
  • Benefits package including health, retirement, and paid time off
Cover Whale

About Cover Whale

Cover Whale, an insurtech founded by experienced insurance and technology veterans, focuses on technology, underwriting, and data to provide innovative insurance programs for the commercial auto industry. Cover Whale's unique Driver Safety Program combines coverage with telematics, dash cams and real-time driver coaching to reduce claims, keep drivers safe and save lives on America's roads. Cover Whale delivers its product through more than 5,000 agents with the industry's fastest, most agent-friendly online quoting experience. Maintaining excellent agent relationships has driven more than $400 million in premium through the Cover Whale platform. With a fundamental belief that safe driving should be rewarded, Cover Whale-insured truck drivers may receive up to 15% off when renewing their auto liability policy.

Industry
Finance & Insurance
Company Size
51-200 employees
Headquarters
New York, New York
Year Founded
2019
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