Kristen Lawler

She has worked on a broad range of projects, including ASC 740 tax provision attest services, federal tax return preparation for financial services companies and formation, qualification and tax advisory services for captive insurance companies. She has extensive experience in accounting for income taxes, statutory tax accounting, federal tax compliance and complex tax technical research.

Lawler was named to Captive Review’s 2024 “Ones to Watch”, and its 2025 “Power 50” list as well as co-authoring the domestic captive chapter in the ABA Deskbook. She has also spoken at many insurance industry conferences, including Texas Captive Insurance Association, Cayman Captive Forum, Captive Insurance Companies Association, Western Region Captive Insurance Conference, Vermont Captive Insurance Association, South Carolina Captive Insurance Association in September 2025 and the Captive Insurance Conference, District of Columbia, in October 2025.

She earned a BA in psychology, with a minor in political science, from Fordham University, received her JD from Pace University School of Law and went on to earn a master of laws (LL.M.) in taxation from Boston University School of Law. She is admitted to practise law in New York and New Jersey and is a member of both state bar associations.

I started in public accounting, focusing on insurance taxation, life, property and casualty and health. With a legal background, I’ve always been drawn to areas where regulation, structure and interpretation intersect with business strategy. That naturally led me to the captive space, where the technical complexity and strategic flexibility align perfectly with both my legal training and tax specialisation.

Captives sit at the crossroads of tax law, insurance regulation and risk management, and I found that intersection intellectually stimulating and professionally rewarding. My involvement deepened as I began advising clients on captive formation, structuring and ongoing tax compliance. What started as a highly technical niche evolved into a long-term professional focus, one that allows me to combine legal analysis, tax strategy and practical problem-solving to help clients achieve efficient, compliant and sustainable outcomes.

I’ve been fortunate to have mentors who invested deeply in my development and shaped how I approach both leadership and client service. Early in my career, I had the privilege of working with individuals like Jim Mannello. With a similar tax and legal background, his technical and practical approach to captive taxation made a lasting impression on me. Jim helped me see how a legal mindset could be applied to the tax and regulatory aspects of captives to create real client value.

I also credit Ed Koral and Jeff Webb, who modelled client service and technical depth. They challenged me to think critically, take ownership and never lose sight of the client’s business purpose behind the numbers. At Crowe, I’ve continued to benefit from mentorship, particularly from Dan Kusaila, whose guidance continues to reinforce the tenets I have come to model in my career.

Awareness. Captive insurance is still viewed as a specialised corner of the insurance and tax world, and many professionals simply don’t know it exists or understand the career paths it offers. It’s not something most people learn about in college or even in the early years of public accounting or risk management. The other limitation is perceived complexity; captives can seem intimidating from the outside. Once people see it’s a blend of finance, tax, law and strategy, they realise how intellectually engaging and rewarding it can be.

I believe that true mentorship goes beyond mere advice. It’s about access and advocacy. Programmes should pair women not only with mentors who can guide them, but with sponsors who actively champion their advancement. That means ensuring women are visible in key projects, conferences and leadership discussions where decisions are made. It also means teaching senior leaders how to recognise and cultivate potential rather than waiting for it to surface.

Inclusion requires intent. Companies must look critically at their pipelines to see who is being developed, promoted and heard. It’s not enough to recruit women into entry-level roles; we need to ensure there’s representation and sponsorship at the decision-making level. Flexibility is also key. The captive space demands deep expertise and retaining that talent means creating career models that support both professional and personal priorities. Finally, visibility matters: putting women in client-facing and thought-leadership roles sends a clear message that their voices belong in this industry.

As mentioned above, visibility is an ongoing challenge. Though improving, women are still under-represented on panels, in boardrooms and in senior leadership roles across the captive ecosystem. That can make it harder for emerging professionals to envision their own paths. Accolades like this one strengthen that visibility and help to drive the improvement for which we are striving.

Intentional representation and structured mentorship will go a long way to achieving these goals.

Professionally, my ambition is to continue growing as a trusted adviser and leader in the insurance and captive space helping clients navigate complexity while building and developing the next generation of professionals in our field. Personally, I’m motivated by the idea of leaving the profession better than I found it – more inclusive, more collaborative and more aware of the value of diverse perspectives. The goal isn’t just to be influential, it’s to use that influence to open doors for others.