Senior Compliance Manager, Cover Whale
$128.2-190k
Plus annual discretionary bonus opportunity
More information about location
Commercial truck insurance provider
Be an early applicant
Commercial truck insurance provider
101-200 employees
Be an early applicant
$128.2-190k
Plus annual discretionary bonus opportunity
More information about location
101-200 employees
Company mission
To use technology to make the world safer.
Role
Who you are
- 8 to 10 years of compliance experience working for property & casualty (P+C) insurance business/insurance intermediary (ideally in both Admitted and Excess & Surplus lines basis)
- 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, and
- 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
- This role is primarily remote (work from home) and requires a dedicated workspace with reliable internet access
What the job involves
- 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
- 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
Our take
Every commercial trucker requires insurance before they can start working, and this can get expensive for businesses that manage large-scale trucking fleets. Despite this insurance spend, commercial trucking fleets still cost businesses enormous amounts of money in road accidents, presenting significant room for improvement in insurance coverage plans.
Cover Whale provides insurance coverage for commercial trucking fleets, leveraging technology to collect hundreds of data points to help identify risks and reduce costs. Whilst the company faces intense competition from other insurance companies, Cover Whale's technology-first approach gives it an edge in providing faster quotes at lower rates compared to its rivals.
So far, the company has driven more than $400 million in premiums through its insurance platform. Cover Whale currently provides coverage throughout nearly all of the continental United States, with firm plans to extend into the remaining territories.
Freddie
Company Specialist at Welcome to the Jungle
Insights
24% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Jul 2025
$40m
EARLY VC
May 2024
$13.8m
EARLY VC
Total funding: $69.3m
Company benefits
- Hybrid Work - Flexible arrangements that balance remote and in-office work
- Flexible PTO - Take the time you need to recharge and maintain work-life balance
- 401(k) Matching - We invest in your future with competitive retirement matching
- Health Coverage - Comprehensive medical, dental, and vision coverage
- FSA Benefits - Healthcare flexible spending accounts for additional savings
- Parental Leave - Generous leave with additional support services for new parents
Company HQ
Financial District, New York, NY
Leadership
Daniel Abrahamsen
(CEO & Co-Founder)Experience working as Project Manager for Allied World from 2015 to 2019. Partner of UnderwritingCloud since 2013.
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