NEW YORK, June 3, 2024 — Cover Whale Insurance Solutions, Inc., a leading insurtech specializing in connected insurance for commercial auto, today announced the appointment of Rachael Dugan as its first General Counsel & Corporate Secretary. Rachael will lead all legal, compliance, corporate governance and regulatory affairs matters for the company and report directly to CEO Dan Abrahamsen. Rachael will also be a member of Cover Whale's executive team and serve as a key advisor on all legal and strategic initiatives to promote the Company's continued growth and expansion.
Extensive Insurance and Legal Leadership Experience
Rachael brings a wealth of experience to Cover Whale, having served in various leadership roles within the insurance and private capital sectors, most recently as:
- General Counsel & Corporate Secretary of Indigo Technologies Holdings LLC, an insurtech platform in the medical professional liability space
- Chief Legal Officer of SiriusPoint Ltd. (NYSE: SPNT), a global diversified (re)insurance business
- General Counsel & Chief Compliance Officer of Reverence Capital Partners LLC, a private capital fund specializing in the financial services sector
- Chief Strategy & M&A Counsel at Marsh McLennan (NYSE: MMC), a leading insurance and professional services company
Her diverse background spans insurtech innovation, global insurance operations, private capital, and large-scale M&A transactions—making her uniquely qualified to guide Cover Whale through its next phase of growth.
Driving Innovation and Compliance
"I'm thrilled to be joining Cover Whale, a pioneering insurtech transforming the commercial trucking space through technology and innovation. With my experience leading the legal and compliance functions for large global businesses and building and scaling insurance businesses, I'm eager to help drive Cover Whale's upward trajectory, reinforcing its commitment to innovation and driver safety." — Rachael Dugan, General Counsel & Corporate Secretary, Cover Whale
A Perfect Fit for Cover Whale's Growth Stage
"Rachael's leadership experience, diverse legal and regulatory expertise and her strategic and transactional background make her a perfect fit for Cover Whale at this stage of our growth. Her contributions will be vital as we expand our connected insurance offerings and explore other potential growth initiatives." — Dan Abrahamsen, CEO, Cover Whale
Strategic Priorities in the New Role
As Cover Whale's first General Counsel, Rachael will focus on several key areas:
Legal & Regulatory Leadership
- Oversee all legal matters and regulatory compliance
- Navigate multi-state insurance licensing and expansion
- Ensure adherence to evolving insurtech regulations
- Build and lead the legal and compliance functions
Corporate Governance
- Establish robust governance frameworks
- Support Board of Directors and executive team
- Manage corporate secretary responsibilities
- Develop policies and procedures for scale
Strategic Growth Initiatives
- Advise on business strategy and expansion plans
- Support M&A activities and partnerships
- Structure new product offerings and market entries
- Navigate complex insurance regulatory landscapes
Risk Management
- Identify and mitigate legal and regulatory risks
- Oversee insurance program compliance
- Manage contract negotiations and vendor relationships
- Protect intellectual property and data privacy
Why This Appointment Matters
Rachael's appointment as Cover Whale's first General Counsel signals several important developments:
Maturation of the Business Adding a senior legal executive demonstrates Cover Whale's evolution from startup to established insurtech platform requiring sophisticated legal and compliance infrastructure.
Preparing for Scale With experience at SiriusPoint (a public company) and Marsh McLennan (a Fortune 500 firm), Rachael brings the expertise needed to support Cover Whale's rapid expansion across states, products, and partnerships.
Regulatory Excellence As Cover Whale navigates 46 states with varying insurance regulations, having a General Counsel with deep insurance regulatory experience is critical to continued expansion.
Strategic M&A Capability Rachael's M&A background positions Cover Whale to pursue strategic acquisitions and partnerships that accelerate growth and market position.
Building a World-Class Executive Team
Rachael joins Cover Whale's executive leadership team at a pivotal time:
- Recent $27.5M investment from Morgan Stanley Expansion Capital
- Expansion to 46 states across all product lines
- Growing network of 4,000+ active agents
- 15,000+ in-force policyholders and counting
- Consistent industry-leading loss ratios
Her addition strengthens Cover Whale's ability to execute on ambitious growth plans while maintaining operational excellence and regulatory compliance.
What This Means for Stakeholders
For Agents & Partners
- Enhanced regulatory compliance across all operating states
- Stronger governance supporting long-term partnership stability
- Professional legal framework for contracts and agreements
- Confidence in Cover Whale's institutional maturity
For Policyholders
- Regulatory protection ensuring proper coverage and claims handling
- Corporate accountability through strong governance
- Data privacy and consumer protection expertise
- Stability backed by professional legal leadership
For Investors & Capacity Partners
- Risk management through experienced legal oversight
- Corporate governance meeting institutional standards
- Strategic advisory on growth and M&A opportunities
- Regulatory navigation enabling market expansion
About Cover Whale
Cover Whale, an insurtech founded by experienced insurance and technology veterans, focuses on technology, underwriting, and data to provide innovative insurance programs for the commercial auto industry.
Operating as a managing general agent (MGA), the company currently has more than 15,000 in-force policyholders, ending 2023 with $225M in GPW while maintaining industry-leading loss ratios. Cover Whale's unique Driver Safety Program combines insurance coverage with telematics and real-time driver coaching to reduce claims, keep drivers safe and save lives on America's roads.
Cover Whale delivers its product through more than 4,000 active agents with the industry's fastest, most agent-friendly online quote and bind experience. With a fundamental belief that safe driving should be rewarded, Cover Whale's safest drivers save by receiving the best insurance rates in the industry.
The company was named 2023 Insurtech of the Year by Program Manager, one of America's Best Startup Employers on Forbes' 2023 list, and more recently, the #3 insurtech to watch in 2024 by PropertyCasualty360.
For more information, visit www.coverwhale.com. Stay updated with Cover Whale on LinkedIn, Facebook, Instagram, and our blog.
Media Contact
For more information about this appointment, please contact:
Cover Whale Communications Email: [email protected] Phone: [Contact information]