Monty Joins the Team: VCIA's AI Assistant for Captive Insurance Insight

As part of its broader strategy to deepen member engagement and deliver value year-round, the Vermont Captive Insurance Association (VCIA) has launched Monty, an artificial intelligence (AI)–powered assistant designed to streamline access to captive insurance knowledge and VCIA resources. 

According to Francis McGill, senior director of marketing at VCIA, Monty emerged from a 2024 strategic planning process that identified three pillars of focus: world-class captive education, national legislative advocacy, and elevated member engagement. "Monty fits squarely into that third pillar," Mr. McGill said, noting that the rollout represents a meaningful step toward enhancing the digital member experience. 

A Tool for Captive Professionals, Built by Captive Professionals 

Monty is not a general-purpose chatbot. Tailored specifically to the captive insurance sector, Monty is trained on VCIA's internal content, member-submitted materials, and trusted sources such as industry reports, regulatory guidelines, and educational publications. This curated training enables it to deliver verified, industry-specific insights in a secure environment—without interactions being used to train external AI models. 

Whether users are asking how to form a captive in Vermont, drafting an executive summary to present to a chief financial officer (CFO), or reviewing regulatory guidance, Monty serves as both a support platform and a source of curated expertise. "We've trained Monty with a depth of information that general AI models don't have access to," Mr. McGill said. "It's a curated AI experience." 

Monty can be used to stay updated on industry trends, access compliance information, explore formation strategies, and get details on VCIA events. Example queries might include the following. 

• "What are the latest trends in captive insurance?" 
• "How do I license a captive in Vermont?" 
• "Write an executive summary to convince my CFO to consider captive formation." 
• "Why should I attend the VCIA annual conference?"

In day-to-day use, Monty is also designed to serve as a troubleshooting resource—giving members an easy way to check on captive questions as they work, helping reduce friction in information access. 

Monty's integration of Captive.com content was also intentional, given its reputation as a primary entry point for newcomers to the industry. "You're incredibly equipped at supplying beginner information, which is a huge part of our audience," Mr. McGill said. "Captive.com has been foundational in helping new entrants make sense of what can be an overwhelming industry." 

Building Community Through Innovation 

Monty's capabilities align with VCIA's broader digital engagement goals. The association is currently developing an online member forum to support peer-to-peer information exchange and best practices. Together with Monty, these initiatives are designed to provide members with flexible access to knowledge and tools throughout the year. 

"Monty represents a major step forward in how VCIA members access information," said Kevin Mead, VCIA president. "With this AI-powered tool, members can get quick, accurate answers, freeing up more time to focus on strategic decisions and industry engagement. It will only become more relevant and useful the more information we feed it." 

"Monty reflects our commitment to modernization," Mr. McGill added. "It's part of a broader mission-driven effort to show that we're not only keeping up with the times—we're moving ahead of the curve. 

"We want Monty to be a tool for the next generation of professionals," he continued. "Students, young risk managers—they're digital natives. They're ready to engage with AI in a way that's intuitive for them." 

Monty also reflects VCIA's broader aim to modernize member services in a sustainable, scalable way. With the association's small but dedicated team, the assistant offers real-time support for common questions while also directing users to curated resources on education, advocacy, and events. 

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While Monty represents a leap in digital service, it is grounded in the work of VCIA's 10-person in-house team. This group brings a mix of industry experience, educational expertise, operational rigor, and creative strategy to support members and evolve the association's offerings. 

"We're not just pushing out a tool," Mr. McGill said. "Monty reflects the knowledge and spirit of a real team that's working every day to serve the captive industry—and that matters." 

Kevin Mead, VCIA president, guides the association's strategic direction with deep experience in global association leadership and finance. Francis McGill, senior director of marketing, leads communications and played a central role in shaping Monty's development. Angie Armour, director of memberships, exhibits, and sponsorships, brings more than 2 decades of advancement and relationship-building experience. Diane Leach, conference education manager, has served VCIA since 1987 and provides institutional knowledge and continuity across decades of programming. 

Jocelyn Lamb, senior director of finance, joined VCIA after more than a decade with the Vermont Department of Financial Regulation, where she served as an insurance examiner. Nikki Fitzcharles, manager of events, draws on extensive nonprofit and operations experience to execute VCIA's signature programming. Drew Frazier, technology manager, leads digital initiatives, including Monty and a forthcoming member portal. Kim McCray-Woodruff, director of learning and professional development, brings strong expertise in adult learning, instructional design, and professional education. 

Supporting the team's daily operations are administrative assistants Joselyn Gilman and Gabriel Daignault, who help ensure member service remains efficient and responsive. 

"Over the past few years, we've had some big transitions, and we've been really fortunate to bring in talented people who are in it for the long haul," Mr. McGill added. "There's real chemistry here, and it shows in the way we collaborate and innovate." 

To explore Monty, visit www.vcia.com and click the chat icon.