Cover Whale

Vice President

• 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.
• 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.

Vice President, Wholesale Brokerage

Customer Support

• Assist customers with policy details, billing inquiries, endorsements, and general coverage questions.
• Support policy renewals by providing clear explanations and guidance.
• Maintain a high level of accuracy in all underwriting and policy-related communications.
• Demonstrate a foundational understanding of underwriting, billing, DriveSmart, and cancellations/reinstatements.
• Develop proficiency in Cover Whale’s knowledge base, binding, billing, cancellation, and reinstatement processes.
• Ensure quality responses that deepen customer relationships and minimize the need for follow-up inquiries.
• Work closely with the DriveSmart, Underwriting and Billing teams to ensure smooth handling of customers’ needs.

Underwriting Associate I – Customer Service Representative

AI Engineer

• Own the platform for agentic engineering pods including orchestration, trust boundaries, and evaluation pipelines
• Ensure collaboration between humans and AI agents is safe and effective
• Coach engineers through a shift in their roles to embrace AI collaboration
• Maintain engineering system integrity and quality gates for AI outputs
• Collaborate with Technical Program Leader to resolve engineering flow bottlenecks

Vice President, Wholesale Brokerage

Underwriting Associate I – Customer Service Representative

Director of AI Engineering