Who is Cover Whale?

Cover Whale is the nation's leading commercial trucking MGA. We improve road safety by combining the insurance products we sell with our telematics-based, data-driven driver coaching and safety program known as DriveSmart. Our program is proven to save lives while delivering better insurance for our drivers. For more information, please visit www.coverwhale.com.  Join us in the mission!

The Role

The Senior Compliance Manager is responsible for leading complex compliance activities, ensuring adherence to regulatory requirements, and providing expert guidance across the organization. This role oversees reporting, filings, and regulatory responses, including audits and consumer complaints, while developing and enhancing policies, procedures, and controls to support a strong compliance framework.

This is a senior, cross-functional role that partners with internal teams to interpret regulations, mitigate risk, and drive strategic compliance initiatives aligned with business objectives. The Senior Compliance Manager also monitors regulatory developments, supports process improvements, and helps build a scalable, efficient compliance function.

Responsibilities

• Resolve complex regulatory compliance matters, conducting comprehensive research, and making informed decisions
• Monitor legislative and regulatory changes applicable to Cover Whale’s business, communicate their impact to the organization, and design solutions to mitigate regulatory compliance risks
• Develop and enhance compliance policies, protocols/procedures for Cover Whale’s core business, as well as new business initiatives, to support strong regulatory compliance posture
• Conduct regular compliance risk assessments to evaluate adherence to Company compliance policies and develop strategies to mitigate identified risks
• Lead the creation, certification, and timely forwarding of Compliance reports to partners internally, ensuring data accuracy and efficient issue-logging
• Independently manage the preparation of accurate and timely responses to insurance consumer complaints received from the State Department of Insurance, BBB, and directly from consumers, ensuring accuracy and compliance with applicable regulations for both consumer complaints and coverage disputes/compliance escalations
• Manage corporate governance and Secretary of State obligations across all entities, including annual reports, good-standing maintenance, registered-agent administration, and entity formations and name changes
• Manage and oversee (i) insurance producer and entity licensing (resident and non-resident), appointments, and licensing-driven commission gatekeeping or Cover Whale, its carrier partners and agents and (ii) OFAC, AML and other mandatory screening requirements
• Oversee compliance with other mandatory reporting and filing requirements – including surplus line taxes, FMCSA, and other state and federal transportation-related filings
• Develop and facilitate compliance training programs for employees to enhance compliance awareness and competence.
• Prepare and provide comprehensive materials and information for internal and external regulatory audits, data calls, surveys, and investigations, and draft detailed responses
• Regularly monitor and analyze regulatory developments and best practices in the insurance and corporate governance sectors to address any changes; build and maintain the Regulatory Change Management process
• Collaborate with management to develop and implement strategic compliance initiatives that align with organizational goals. Verify and ensure that corrective actions are effectively implemented to confirm that mitigation plans are successful
• Actively incorporate AI and other emerging technologies into daily workflows to drive efficiency and innovation, while maintaining sound judgment, data integrity, and compliance standards

Requirements

Requirements

• 8 to 10 years of compliance experience working for a property & casualty (P+C) insurance business/insurance intermediary (ideally in both Admitted and Excess & Surplus lines)
• Bachelor’s degree from an accredited university (Legal degree preferred)
• Experience in commercial auto insurance segments preferred
• In-depth knowledge of the industry's standards and regulations.

Must-Have Skills/Abilities:

• Excellent written and verbal communication skills
• Deep knowledge of insurance regulatory requirements in the P+C insurance space (admitted + surplus lines)
• Ability to analyze complex regulations and problems, exercise strong judgment and develop solutions to balance compliance risks with business goals 
• Strong organizational skills and ability to take initiative on compliance projects
• Methodical and diligent with prioritizing and executing on compliance obligations
• Sound judgment and high ethical standards

Working Conditions

This role is primarily remote (work from home) and requires a dedicated workspace with reliable internet access. The position requires regular virtual collaboration with cross-functional teams and leadership. Occasional travel may be required for company meetings, offsite planning sessions, or business initiatives. Must be able to work Eastern Standard Time.

Benefits

At Cover Whale, we believe in transparent and equitable compensation practices. The expected base pay for this role has a range of $128,232 to $190,000 per year. Final base pay is determined based on several factors, including skills, experience, and geographic location (i.e., NY-based at the higher end of the range)

Base pay is only part of our total compensation package, which also includes:

• Annual discretionary bonus opportunity
• Comprehensive health, dental, and vision insurance
• 401(k) company match up to 4 %
• Generous paid time off and company holidays. 

Cover Whale works to maintain the best possible environment for our employees, where individuals can learn and grow with the company. We strive to provide a collaborative environment where each person feels encouraged to contribute to their processes, decisions, planning, and culture.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law