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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...

Who is Cover Whale? Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. We provide easy insurance options for our drivers at industry-leading insurance loss ratios for the insurance companies that support Cover Whale. The Commercial Auto and Trucking segment of the insurance industry badly needs our help, and so do the hard-working drivers who have been struggling with ever-increasing insurance costs year after year. Join us in the mission! The Role Cover Whale is looking for a motivated, client-focused Agency Success Associate to support the growth of our agency partner network. Reporting to the Director of GTM, you'll be an integral part of the Growth team — helping manage the onboarding and activation of new agency partners from initial evaluation through their first steps with Cover Whale....

Who is Cover Whale? Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. We provide easy insurance options for our drivers at industry-leading insurance loss ratios for the insurance companies that support Cover Whale. The Commercial Auto and Trucking segment of the insurance industry badly needs our help and so do the hard-working drivers who have been struggling with ever-increasing insurance costs year after year. Join us in the mission! The Role As an Underwriting Associate 1, you will be the first point of contact for policyholders and agents, providing essential phone support and assisting with general underwriting and service-related inquiries. This role is ideal for a detail-oriented professional looking to gain experience in underwriting, policy servicing, and customer support. You will...

Who is Cover Whale? Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. Cover Whale offers easy, industry-leading insurance for commercial auto and trucking, aiding struggling drivers facing rising costs. Join us in the mission! The Role We are rapidly expanding and looking to build a dynamic team of Business Development professionals, and are looking for a Business Development Associate located in the Central Region (Chicago preferred) Reporting to the Retail Distribution Lead, the Business Development Associate will support strategies aimed at increasing premium production in their region. This role involves managing smaller, established partners and newly onboarded partners, ensuring their successful integration and growth. The Associate will also develop strategies for these...

Who is Cover Whale? Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. Cover Whale offers easy, industry-leading insurance for commercial auto and trucking, aiding struggling drivers facing rising costs. Join us in the mission! The Role We are rapidly expanding and looking to build a dynamic team of Business Development professionals, and are looking for a Business Development Associate located in the West Region (Washington, Idaho, Nevada, Arizona, Wyoming, Utah, or Colorado), working remotely on Pacific Time hours. Reporting to the Retail Distribution Lead, the Business Development Associate will support strategies aimed at increasing premium production in their region. This role involves managing smaller, established partners and newly onboarded partners, ensuring their successful...

Who is Cover Whale? Cover Whale improves road safety by combining the insurance products we sell with our data-driven driver coaching and safety program. Our safety program is proven to save lives while delivering better insurance for our drivers. We provide easy insurance options for our drivers at industry-leading insurance loss ratios for the insurance companies that support Cover Whale. The Commercial Auto and Trucking segment of the insurance industry badly needs our help, and so do the hard-working drivers who have been struggling with ever-increasing insurance costs year after year. Join us in the mission! The Role:  The Business Development Manager (BDM) – will report to the Retail Distribution Lead and will be responsible for managing a defined portfolio of retail distribution partners across a specific region. The BDM will execute strategies to increase premium production, deepen engagement with existing Tier 1 and Tier 2 partners, and identify new...