Cover Whale

Role Description 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 adjust 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. Qualifications - 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 - Base Salary commensurate 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.

• 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.

Role Description 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 be responsible for answering inbound inquiries (by phone and/or email) quickly and efficiently, ensuring first-call resolution whenever possible, and maintaining high-quality service standards. - 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. Qualifications - 1+ years of insurance experience, preferably in underwriting or policy servicing. - Strong customer service and phone communication skills, with experience handling complex insurance inquiries. - Proficiency in business applications like Zendesk, HubSpot, Slack, and Excel. - Strong problem-solving skills and ability to work in a fast-paced, team-oriented environment. - Spanish fluency is a bonus but not required. Requirements - The anticipated base salary for this position will be between $52,232.80 and $66,000 per year for remote candidates at the beginning of employment. - For hybrid positions in New York, the salary will be between $62,000 and $70,000. - The base salary will be determined on an individualized basis, taking into account factors such as geographical location within the United States and relevant experience. - The base salary constitutes only one component of the overall compensation package, which also includes a discretionary bonus and various benefits sponsored by Cover Whale. Benefits - Health Care Plan (Medical, Dental & Vision) - Retirement Plan (401k, IRA) - 4% match - Life Insurance (Basic, Voluntary & AD&D) - Paid Time Off (Vacation, Sick & Public Holidays) - Paid Family Leave (Maternity, Paternity) - Tuition Assistance - Professional Training & Development

• 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

About the Role This is not a rebranded Director of Engineering. It is a new position purpose-built for a new way of building software. Cover Whale is operating an agentic engineering model where pods of product managers, engineers, and AI agents deliver production software together. The Director of AI Platform Engineering owns the platform those pods operate on — the agent orchestration layer, trust boundaries, human-in-the-loop controls, and evaluation pipelines that make it safe and effective to delegate work to AI at production scale. You will be a player-coach: hands-on building the platform while also leading and developing the engineering team. Your mandate is to ensure that humans and AI agents collaborate safely, reliably, and at velocity. What You'll Own - Agentic Platform Architecture Human-in-the-loop boundaries — setting trust thresholds where AI-generated output is auto-approved versus escalated for review - Prompt and spec evaluation pipelines — the systems that validate whether AI-generated code, tests, and configurations meet production standards before reaching a human reviewer - The end-to-end specification-through-deployment pipeline: how specs become agent instructions and how agent output becomes production code - Evaluation and integration of emerging AI tooling, models, and agent frameworks Engineering System Integrity - Quality gates calibrated for AI-augmented velocity — ensuring AI-generated output meets production standards Engineering standards: branch protection, test coverage, CI/CD rules, and deployment integrity - Architectural escalation path for engineers facing technical blockers - Collaboration with the Technical Program Leader on engineering flow patterns and systemic bottlenecks People Leadership for an Agentic Team - Coaching engineers through the identity shift from "I write code" to "I orchestrate AI agents and own outcomes" Career development, performance accountability, and 1:1s — with expectations calibrated to the expanded role of delegate, review, and own - Building team culture where engineers treat AI agents as force multipliers, not threats What You Won't Own - Product direction, spec writing, or feature prioritization (that's the product management team's role) - Pod-level delivery — the pod is PM + Engineer + AI Agents; you govern the platform they operate on - Company-wide AI enablement and adoption (that's the AI Enablement Lead

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 partner cohorts and provide key insights on their portfolio's makeup during quarterly reviews. Responsibilities: - Collaborate with underwriting, marketing, and development teams to develop, manage, and drive distribution and partner premium generation. - Oversee a portfolio of emerging and lower-volume partners, with accountability for fostering relationships, identifying growth potential, and ensuring consistent performance. - Provide pipeline support by researching target markets, potential partners, and competitive intelligence. - Represent Cover Whale in meetings with distribution partners. - Identify and execute opportunities to further engage with current partners. - Establish, track, and report on KPIs while routinely meeting or exceeding goals. - Assist in the constant improvement of business development, partner management, and onboarding processes. - Drive a better brand image amongst our current trading partners and prospects with continuous outreach. - Support event and field presence efforts within the assigned region, including preparing partner materials and assisting with logistics for retail-focused engagements. - Monitor partner performance trends and flag opportunities or risks to the Business Development Manager or Leader. - Maintain CRM accuracy by updating partner interactions, notes, and performance data promptly. - Other duties as assigned.

• Manage a defined portfolio of retail distribution partners across the South-Central United States. • Execute strategies to increase premium production and deepen engagement with partners. • Maintain approximately 50% of time in-field travel across the Midwest. • Balance in-person engagement with strategic account management. • Cultivate and expand agency partnerships to achieve revenue targets within your territory. • Represent Cover Whale in meetings with distribution partners, seminars, trade shows, and networking events. • Prospect new distribution partners and agents. • Identify opportunities to further engage with current partners. • Establish, track, and report on KPIs while meeting or exceeding goals. • Help improve business development, partner management, and onboarding processes. • Establish a positive distribution team culture. • Carry out market trend research and competitor analysis. • Produce Strategic development goals to increase revenue growth with trading partners. • Research, plan, and implement prospective accounts in target markets. • Continuously outreach to current and prospective partners to improve brand image.

• Collaborate with underwriting, marketing, and development teams to develop, manage, and drive distribution and partner premium generation. • Oversee a portfolio of emerging and lower-volume partners, with accountability for fostering relationships, identifying growth potential, and ensuring consistent performance. • Provide pipeline support by researching target markets, potential partners, and competitive intelligence. • Represent Cover Whale in meetings with distribution partners. • Identify and execute opportunities to further engage with current partners. • Establish, track, and report on KPIs while routinely meeting or exceeding goals. • Assist in the constant improvement of business development, partner management, and onboarding processes. • Drive a better brand image amongst our current trading partners and prospects with continuous outreach. • Support event and field presence efforts within the assigned region, including preparing partner materials and assisting with logistics for retail-focused engagements. • Monitor partner performance trends and flag opportunities or risks to the Business Development Manager or Leader. • Maintain CRM accuracy by updating partner interactions, notes, and performance data promptly. • Other duties as assigned.

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:  For this role, we are looking for candidates who are physically residing in the North East region. The Business Development Manager (BDM) – will report to the Senior Business Development Manager 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 high-potential relationships within the region. This role requires maintaining approximately 50% of time in-field travel by plane. The BDM will balance in-person engagement with strategic account management, ensuring that partner relationships are actively nurtured and aligned with Cover Whale’s growth objectives. Responsibilities will include, but not be limited to:  - Collaborate with underwriting, marketing, and development teams to develop, manage, and drive distribution and partner premium generation. - Generate new relationships and develop current relationships to meet or exceed revenue goals with agency partners located in your territory.   - Represent Cover Whale in meetings with distribution partners, seminars, trade shows, and networking events. - Prospect new distribution partners and agents. - Identify and execute opportunities to further engage with current partners. - Establish, track, and report on KPIs while routinely meeting or exceeding goals. - Assist in the constant improvement of business development, partner management, and onboarding processes. - Establish a positive distribution team culture. - Carry out market trend research and competitor analysis to discover customers' needs. - Produce Strategic development goals to increase revenue growth with our trading partners. - Research, plan, and implement prospective accounts in target markets.  - Drive a better brand image amongst our current trading partners and prospects with continuous outreach. - Other duties as assigned.

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:  The Business Development Manager (BDM) – Retail, Midwest will report to the Retail Distribution Lead and will be responsible for managing a defined portfolio of retail distribution partners across the South-Central United States. The BDM will execute strategies to increase premium production, deepen engagement with existing Tier 1 and Tier 2 partners, and identify new high-potential relationships within the region. This role requires maintaining approximately 50% of time in-field travel across the Midwest, including but not limited to partners in Arkansas, Kansas, Louisiana, Oklahoma, and Texas. The BDM will balance in-person engagement with strategic account management, ensuring that partner relationships are actively nurtured and aligned with Cover Whale’s growth objectives. Responsibilities will include but not be limited to:  - Work with underwriting, marketing, and development teams to manage and drive distribution and partner premium generation. - Cultivate and expand agency partnerships to achieve revenue targets within your territory. - Represent Cover Whale in meetings with distribution partners, seminars, trade shows, and networking events. - Prospect new distribution partners and agents. - Identify and execute opportunities to further engage with current partners. - Establish, track, and report on KPIs, while routinely meeting or exceeding goals. - Help improve business development, partner management, and onboarding processes. - Establish a positive distribution team culture. - Carry out market trend research and competitor analysis to discover customers' needs. - Produce Strategic development goals to increase revenue growth with our trading partners. - Research, plan, and implement prospective accounts in target markets.  - Continuously outreach to current and prospective partners to improve brand image. - Other duties as assigned.