Emerging Talent Highlights Practical Captive Strategies at CICA 2025 Student Essay Panel

The 2025 Captive Insurance Companies Association (CICA) Conference once again spotlighted rising talent in the captive insurance field through its annual student essay contest panel. Designed to encourage applied learning and creative problem-solving, the competition drew participation from students across the country who were tasked with developing fictional case studies illustrating how captive insurance could be used to address complex risk management challenges.

This year's panel featured the top three finalist teams: students from the University of Wisconsin—Madison, St. Mary's University, and Connecticut College. Sponsored by Hylant Global Captive Solutions, the contest paired each student team with an industry mentor to refine their proposals and prepare for the panel presentation.

Second-place finalists Matthew Sharretts and Samuel Brockelman of Connecticut College participated via pre-recorded video while studying abroad in Spain and Germany. Although their discussion is not included here, their presentation was shared with the conference audience and recognized for its thoughtful approach and technical merit.

The University of Wisconsin—Madison team of Rachel Claire Gibson and Ella Pernsteiner earned first place for their analysis of risk financing strategies for a fictional hospitality group, Seagrass Lodges.

Third place was awarded to Isabella Martinez and Skilee Soto of St. Mary's University, who developed a captive solution for a large stadium and event venue.

Addressing Operational Resilience for a High-Volume Event Venue

Ms. Martinez and Ms. Soto of St. Mary's University presented a proposal centered on Acadia Field, a fictional 100,000-seat stadium that hosts over 600 events annually. The team identified four key exposures: general liability from large crowds, weather-related cancellations, VIP security risks, and food and liquor safety concerns.

"Traditional insurance often has rising premiums and coverage limitations, which can leave gaps in protection," Ms. Martinez noted. Ms. Soto added that venues like Acadia Field would benefit from the flexibility and control offered by captive insurance, especially in tailoring coverage levels to different event types and funding proactive measures such as staff training.

The proposal emphasized the advantages of parametric insurance for weather-related risks and pointed out that security threats involving high-profile individuals—an often excluded category in traditional policies—could be more effectively addressed through customized captive coverage. Ms. Martinez cited the 2017 Manchester Arena bombing as a cautionary example where stronger pre-event security planning might have mitigated loss severity.

The team acknowledged the initial capital requirements and regulatory considerations associated with forming a captive, emphasizing the importance of feasibility analysis, governance, and long-term strategic planning. "Captive insurance is not a set-it-and-forget-it method," Ms. Martinez explained. "Ongoing risk monitoring and expertise are essential."

Throughout the contest process, Ms. Martinez and Ms. Soto were mentored by Carter Cappon of Hylant. "He was telling us real-world scenarios that he's faced in his profession," Ms. Soto shared during the panel. Mr. Cappon noted that the collaboration provided an opportunity to explore the fictional scenario in more depth. "We were essentially setting up a micro-captive with them—it was a good process," he said.

Both students are interning at Munich Re this summer—Ms. Martinez in underwriting and Ms. Soto in claims—and noted that the experience of participating in the contest has sparked a potential interest in pursuing a career in captive insurance.

Tailored Captive Approach for a Coastal Hospitality Chain

University of Wisconsin—Madison sophomores Ms. Gibson and Ms. Pernsteiner earned top honors for their analysis of Seagrass Lodges, a fictional chain of 15 oceanfront hotels on the wildfire-prone West Coast. The team considered both single-parent and group captive models and ultimately proposed a customized captive structure that included reinsurance integration, parametric coverage for catastrophe risks, and actuarial modeling to assess reinsurance thresholds.

"Your aim is to provide safety and security for your client," Ms. Gibson said in her opening remarks. Their recommendation included a cost-benefit analysis and feasibility study to determine whether the captive would deliver long-term financial value. The plan also incorporated reinsurance to manage large-scale exposures and proposed the use of Monte Carlo simulation to evaluate attachment points for excess-of-loss coverage.

The team highlighted operational strategies—such as improved flooring for slip prevention and employee safety training—to reduce claims frequency and improve outcomes under a high-deductible model. These measures would be supported by retained earnings within the captive.

When evaluating captive domicile options, Ms. Gibson acknowledged the strengths of multiple US jurisdictions. "With all love and peace in mind to all the other domiciles," she said, "we do think Vermont was the best domicile selection for this property." The team cited Vermont's regulatory flexibility, established infrastructure, and supportive environment for captive formations as key reasons for their recommendation.

Throughout the contest process, the students were supported by Caroline Erdman from Hylant, who served as a mentor and helped guide the development of their presentation. "Working with them was awesome," Ms. Erdman said during the session, noting their professionalism and attention to detail. "Bouncing ideas and going through the essay step by step was a lot of fun."

Reflecting on the experience, both students emphasized the value of applying classroom knowledge in a practical setting. "It gave me a real-world lens on what we've been talking about in class," Ms. Pernsteiner said. Ms. Gibson noted that continuous research and problem-solving were essential. "We were constantly looking for holistic solutions as new risks or challenges came up."

A Pathway into the Profession

The student panel closed with a Q&A moderated by Anne Marie Towle, CEO of Global Risk and Captive Solutions at Hylant. Ms. Towle emphasized the significance of early exposure to the industry and noted that the essay contest continues to serve as a valuable bridge between academia and practice.

Students learned about the contest through professional networks, Gamma Iota Sigma, university faculty, and events such as the Chicagoland RIMS forum. Several credited the mentoring process as instrumental in their success, with mentors like Mr. Cappon and Ms. Erdman providing insight into real-world applications of captive structures.

Ms. Towle concluded by encouraging all attendees to support student engagement in the industry. "This is more than a contest—it's about cultivating the next generation of captive insurance professionals."