In celebration of its 40th anniversary, Vermont Captive is featuring a series throughout the year highlighting companies and people that service the captive insurance industry.

Fresh out of college in the 80’s, Diane Leach began her career in the captive industry with American Risk Management (ARM). Later, in 1987, just 6 years after Vermont passed captive enabling legislation, Diane joined the Vermont Captive Insurance Association (VCIA) as its first Executive Director and is now its Director of Education and Program Planning. Diane ran the organization back then out of her home office and garage in Stowe, Vermont, a time many look back on with fond memories.

Diane has been instrumental in the success of the VCIA as the largest captive insurance trade association in the world. During her decades-long career with VCIA, she has worked tirelessly to develop, promote and orchestrate educational and networking programs for VCIA’s members. One of the many things she’s learned during her career is that the captive industry is about transforming challenges into opportunities.

The very nature of the captive industry is to transform challenges that the commercial insurance market faces into opportunities for businesses to protect themselves from risks associated with their operations. “I find those sorts of challenges inspire innovation, and I enjoy helping to enable that,” Diane says. “VCIA plays an important role in educating its members on those issues and finding ways to address them, whether through educational events like our webinars, conferences and roadshows, or through VCIA’s advocacy at the federal and state levels.”

“And VCIA is not just about education and advocacy,” Diane adds. “It’s about connection and collaboration. Bringing captive owners, managers, service providers and regulators together creates an important synergy which is critical for solving complex risk management issues.”

“The VCIA Annual Conference has a vibrance which provides a great arena for just this sort of collaboration,” Diane says. Held in Vermont every year, and now in its 37th year running, this 4-day event hosts over 1,000 professionals annually and is a prime opportunity for members to learn from and engage with their peers. “It’s a major group effort to pull it off each year, and our success is in large part due to an amazing volunteer conference task force, comprised of 30 – 40 VCIA Members, as well as a very hard-working small staff,” Diane remarks.

Each year, just a few weeks after the annual conference, Diane and her team cull through evaluations to identify current educational needs and trending captive topics, always with the goal of making the next year’s event even better.

The pandemic, however, presented its own set of challenges. With in-person events being suspended, VCIA had to figure out how to present all the educational content that had already been developed, in a new way. “In 2020, we were one of the first in the industry to change to a virtual conference format, and felt, as industry leaders, that we should set the tone and focus on a quality event,” Diane explains. “We worked hard, in an accelerated timeline, to identify the way to execute an event which was educational but also dynamic and fun. We researched and found good technology, and tailored the conference content (educational sessions, networking, exhibits, keynote speakers) to work within that space. While VCIA was hoping to return to an in-person format for the 2021 conference, they concluded early on that the time just wasn’t right for everyone’s safety. “So, incorporating what we learned from the prior year, we created an even better virtual conference for 2021,” Diane shares.

Of course, VCIA would not be the largest captive trade association without the support of the Vermont regulators. “VCIA truly values the relationship we have with the Vermont regulators. Their insight and forward-thinking approach helps us determine what our members should be thinking about, not only now but down the road,” Diane states.

You might think that constantly looking to educate the industry about challenges they face and opportunities arising from them, coupled with the desire to improve VCIA’s offerings every year, might be daunting. But, as Diane says, “the people in this industry are incredible, and they make the work really enjoyable. Captive owners, the regulators, managers, service providers – they are an intelligent and interesting cast of characters that take their work seriously but make things fun at the same time.”

Diane looks forward to continuing to elevate VCIA’s offerings and knows the industry will be ready for the challenges and opportunities ahead.