Different Captive Conferences, Same Conversations

I attended four captive insurance conferences during 2025: the Vermont Captive Insurance Association Conference, the South Carolina Captive Insurance Conference, the National Risk Retention Association Annual Conference, and the Tennessee Captive Insurance Conference. I did so wearing two hats: one shaped by my prior experience as a state insurance regulator and financial examiner, and another informed by my current role overseeing regulatory compliance and captive management for risk retention groups and captive insurers. That combination tends to shape what I notice, what I listen for, and what stands out.

I do not attend conferences casually. Until this year, my only captive conference experience came through several events hosted by the now-defunct Alabama Captive Insurance Association. Seeing multiple domiciles and organizations up close in such a short period of time gave me a much broader lens into how the captive industry is showing up right now and where expectations are clearly headed.

What stood out was not any single presentation, but the consistency of the themes across all four forums. Regardless of domicile, regulator, or business model, the same underlying issues surfaced repeatedly: governance maturity, documentation discipline, and the growing expectation that boards understand not just what decisions are made, but how and why they are made. Different captive conferences, same conversations.
Governance as an Operational Discipline

Governance was everywhere. Not as a buzzword and not as a box-checking exercise, but as something practical and operational. Regulators, captive managers, actuaries, auditors, and board members all kept coming back to the same issues: clarity of board roles, quality of documentation, and whether boards are actually engaged or simply present.

From a regulatory standpoint, none of this is new. Many examination findings are not driven by capital deficiencies, but by weak governance practices and thin documentation. From the industry side, those same weaknesses tend to show up as delays, expanded scrutiny, or strained regulatory relationships.

What felt different this year was how little disagreement there was. Governance is not something that can be deferred, delegated entirely to advisors, or addressed after the fact. It is increasingly treated as foundational. Capital may get you in the door, but governance determines how long you stay there.

In addition to observing these themes, I have found value in contributing to the broader conversation. This year, I will be participating in the Vermont Captive Insurance Association Conference as part of the “Boardroom Bootcamp” sessions, which are designed to provide practical, real-world insight into board governance, oversight, and decision-making in a captive context. Opportunities like this reflect the industry’s increasing focus on equipping boards with the tools and perspective needed to meet evolving expectations.

Governance and the Long View

Conferences are often a preview of where scrutiny is heading. Governance issues rarely appear overnight. They develop slowly through patterns of inattention, unclear oversight, and undocumented decision-making. By the time they surface formally, they are usually well established.

The sustained focus on governance across conferences tells me the industry is maturing. Boards that understand their role, challenge management when appropriate, and clearly document their deliberations are better positioned not only for examinations, but for long-term stability and credibility.

Conferences Only Work if You Do

Conferences are sometimes dismissed as networking exercises or continuing education requirements. In my experience, you get out of them exactly what you put in.

Some of the most valuable moments did not happen in formal sessions. They happened in side conversations with regulators, discussions with peers who are dealing with the same issues in different jurisdictions, and candid exchanges with service providers who see patterns across multiple companies.

I have watched people attend the same conference and walk away with very different takeaways. The difference is rarely the agenda. It is engagement.

I tend to experience conferences with a notebook in hand. I take pages of notes, jot down quotes that resonate, and snap photos of slides that strike me as meaningful in the moment. I leave with notebooks full of observations and reminders, many of which I revisit long after the conference ends.

At some point, though, it occurred to me that what stands out to me may not stand out to someone else. Just as importantly, no matter how thorough my notes are, I could never do the content justice for someone who was not there. The nuance, the tone of the conversation, the questions asked, and the informal dialogue that follows a session are often as important as the material itself.

That realization reinforced something I strongly believe. If you are involved in the captive industry, it is important to show up. Attend the conferences. Take in the content. Ask the questions. Engage with regulators and peers. And support the associations in the domiciles where you operate or that stand up on behalf of your company. These forums are not just about information sharing. They are where expectations are shaped, relationships are built, and the direction of the industry quietly takes form.

While I was not eager to stand outside in the heat, sweating through outdoor receptions in South Carolina and Vermont, I did. Those moments turned out to be some of the most valuable. I met people I had not met before and, just as importantly, caught up in person with colleagues I normally only communicate with by email. Conversations that start in inboxes often deepen when they happen face to face, even under less-than-ideal conditions.

Engagement Takes Effort

As someone who falls closer to the introverted end of the spectrum, I do not arrive at conferences expecting engagement to happen organically. I prepare for it. Before each conference, I set simple, intentional goals, such as introducing myself to at least three new people each day and looking for opportunities to be helpful rather than transactional.

That usefulness may take the form of answering a regulatory question, offering perspective from prior experience, or simply helping two people make a connection they did not realize they needed. That approach changes the experience. Conferences become less about self-promotion and more about shared problem-solving. The conversations are better, and the insights are sharper.

Some professionals attend far more conferences. Attending four in such a short span reminded me why I do not. Meaningful engagement takes energy. Conferences require preparation, presence, and follow-through. Without that, even the best programming becomes background noise. For me, fewer conferences with deeper engagement produce far better results.

Different Domiciles, Similar Pressures

Despite differences in statutes and processes, expectations across jurisdictions are converging. Governance standards, board accountability, and transparency are becoming less negotiable everywhere.

At the same time, very real domicile-level issues were discussed openly. Staffing turnover within insurance departments came up repeatedly. In some states, institutional knowledge has been lost, and newer regulators are being asked to manage increasingly complex captive and RRG oversight with limited experience and resources. In some cases, regulators go radio silent and fail to respond to even the simplest inquiries.
There was also candid discussion about non-domiciliary states asserting regulatory authority that is preempted by federal law. For risk retention groups in particular, this creates confusion, inconsistency, additional expense, and unnecessary friction.

Layered on top of this is the constant pressure states feel around accreditation. There was discussion that the NAIC may have set its sights on regulation of non-RRG captives. In some cases, concern over accreditation appears to be influencing captive oversight in ways that were never intended. For RRGs, the impact is amplified. These were not isolated comments. They were themes repeated across conferences by regulators, captive managers, and industry participants.

Technology, Economics, and Compounding Pressure

Artificial intelligence and the broader economic environment were also recurring topics. The discussions around AI were practical, not speculative. Regulators and captive managers alike are beginning to use AI tools to increase efficiency, flag issues, and streamline analysis.

What became clear is that AI does not eliminate judgment. It shifts it. Without strong governance, AI can amplify problems just as easily as it can solve them. That reality matters, particularly for RRGs, where decisions and documentation are already subject to layered scrutiny.

Overlaying all of this is an economic environment that continues to feel uncertain. Inflation, tariffs, interest rates, tighter capital markets, and volatility across insurance lines were discussed. Economic pressure tends to expose weaknesses more quickly and heighten regulatory sensitivity.

Taken together, staffing instability, accreditation pressure, AI adoption, and economic uncertainty help explain why so many conversations this year felt urgent and candid. They also reinforce why governance and engaged boards are no longer optional.

Differing Strengths, Shared Values

While common themes emerged across conferences, each also demonstrated distinct strengths.

One conference, in particular, stood out for the depth and timeliness of its educational content. The National Risk Retention Association Annual Conference addressed issues that were not only current, but directly aligned with the operational and governance challenges facing risk retention groups today. The sessions were substantive, practical, and engaging, prompting active dialogue rather than passive attendance. From both an educational and professional standpoint, it was one of the most effective and impactful conferences I have attended.
The Vermont Captive Insurance Conference, by contrast, offered a different but equally valuable strength. While its educational programming followed a more traditional structure, Vermont distinguished itself by convening a comprehensive cross-section of captive service providers in one place. That concentration created an environment conducive to collaboration, thoughtful discussion, and cross-disciplinary problem-solving. It also reflected a sense of community that is hard to replicate. One association employee provided each attendee with maple syrup from her family farm, a small but memorable gesture that underscored the personal investment behind the conference.

As a first-time attendee at all of these conferences, I will admit that I occasionally felt a bit like a fish out of water. One thing Vermont did particularly well was intentionally welcoming first-time attendees. VCIA offered each new attendee the option to select a conference ambassador. I scanned the list and immediately noticed an individual associated with one of our clients. While I had never met her in person, I recognized the connection and selected her without hesitation. She reached out to me before the conference, answered my questions, and then checked in throughout the event. She spent time with me at one of the social events and introduced me around, which made a meaningful difference in my experience.

I also found the VCIA staff to be genuinely open to feedback. During the conference, I shared my dissatisfaction with the existing conference app and showed staff the app used by the Society of Financial Examiners, which I view as an excellent example of effective conference technology. While attending the NRRA conference later, one of the VCIA staff members made a point to find me and let me know that VCIA had selected the same vendor used by SOFE to build a new app for future VCIA conferences. It was encouraging to see feedback taken seriously and translated into action, and it reinforced the value of associations that are willing to listen, adapt, and improve. This was just one example, but there were several.

South Carolina offered yet another, very different strength. The conference was small, intimate, and held in a beautiful setting, which created an environment where conversations came easily and relationships could deepen quickly. The size made it easier to engage meaningfully with regulators, service providers, and peers without the formality or pace that larger conferences sometimes require. There is real value in that kind of setting, particularly in an industry where trust and accessibility matter.

Tennessee brought yet another dimension. In Nashville, the conference created space for connection in a uniquely authentic way, including a singer-songwriter night opened by members of the association themselves. If you missed it, you truly missed out. Moments like that foster connection, shared experience, and trust, intangibles that matter just as much as technical programming in an industry built on relationships.

Regulators Show Up

Another thing that stood out was regulator accessibility. Regulators are not limiting their engagement to conferences hosted by their own domiciles. Many travel to conferences hosted by other jurisdictions, and those conversations are often among the most informative.

These discussions provide insight you cannot get from statutes or filings alone. Following these conferences, Risk Services continued discussions with certain domiciles and ultimately decided to file applications in those jurisdictions. Those decisions were shaped by ongoing dialogue with regulators and further informed by in-person conference discussions and subsequent follow-up. Bottom line, conferences matter because they reveal what paper and phone calls never will.

Who Shows Up Tells You a Lot

Seeing multiple domiciles side by side reinforced something I have believed for a long time. Who shows up matters.

When directors, commissioners, or even governors are present, it signals commitment. It suggests resources, prioritization, and accountability. When leadership is consistently absent, it raises questions, whether intended or not.

If you want to understand whether a domicile is likely to support its captive industry over the long term, look beyond marketing materials. Look at who shows up.

Not every meaningful moment, however, came from policy discussions or governance debates. Know who else showed up? Taco, the service dog. A couple of conferences went the extra mile and even had her name tag waiting on arrival.

We all knew we were not supposed to pet her. Many of us failed, including me. As we moved through the halls and meeting spaces, more than a few otherwise disciplined professionals briefly forgot themselves and offered a quick, well-meaning pat.

Her calm presence brought warmth to otherwise serious environments and served as a reminder that composure and quiet confidence matter.

A Notable Divide for Risk Retention Groups

One additional theme became clear. With the exception of the National Risk Retention Association Annual Conference, most of the conferences I attended were geared primarily toward non-RRG captive structures. That is not intended as criticism, but as an observation.
Between conference sessions, that divide was underscored by candid conversations I had with regulators from a couple of domiciles who noted that they were less enthusiastic about licensing additional risk retention groups at this time, citing workload demands and accreditation pressures. That kind of candor is actually helpful. It provides clarity and allows companies and managers to make informed decisions based on reality rather than assumption. Clarity, even when unfavorable, is preferable to uncertainty.

National Risk Retention Association and the Value of Real Dialogue

The NRRA Annual Conference stood apart. Breakout sessions provided informal access to regulators and created space for real conversation. Attendees were encouraged to engage, not just listen.

Conversations with other captive managers revealed common challenges across jurisdictions, including registration delays, inconsistent filing expectations, and lack of responsiveness in certain states. In some cases, jurisdictions are signaling, formally or informally, that they are effectively closed for business for the foreseeable future. Hearing those same concerns echoed by others reinforced that these issues are systemic, not isolated.

Awards are often presented at industry conferences, but at NRRA they felt particularly meaningful. At the 2025 conference, Heather Ross of Risk Services was awarded the Karen Cutts Visionary Achievement Award, a well-deserved recognition of leadership, service, and long-standing commitment to the risk retention group community. Moments like that reinforced the sense that NRRA is not just convening conversations, but recognizing the individuals who help move the industry forward.

NRRA’s “Helps to Help” in Practice

The theme of “NRRA helps to help” was not just a tagline. It showed up in every session. The tone was collaborative, practical, and focused on shared problem-solving. Even the final session felt more like a group conversation than a presentation.

Every session was engaging. If you did not attend, you genuinely missed out. And if it is not already obvious, this was my favorite conference this year.

The work NRRA does on behalf of risk retention groups deserves deeper discussion. That may be another article. Stay tuned.

A Broader Call to Engagement

As an aside, and very much aligned with many of the themes discussed here, a new captive association, the Alabama Alternative Risk Alliance, has recently been formed. Its purpose is to provide a forum for education, collaboration, and constructive engagement around alternative risk and captive insurance issues.

If you want to be part of the solution and have a voice in how captive industries evolve, participation matters. Supporting the captive associations in the domiciles where you operate is one of the most effective ways to do that. These organizations serve as important bridges between industry participants and regulators, particularly in times of change.

RRGs Leave No Room for Weak Governance

Risk retention groups (RRGs) operate under constant scrutiny across multiple jurisdictions. Governance failures show up quickly and often publicly.

Risk Services has formed more risk retention groups than any other captive manager and manages one of the largest portfolios of RRGs by count in the market. That scale provides a concentrated view of how governance decisions are evaluated in real time.

Nothing tests governance quite like an RRG. Boards operating in this space need to be engaged, informed, and prepared. The margin for error is small, and the consequences of weak oversight are immediate.

Final Thoughts

Conferences do not change organizations. People do.

When approached intentionally, conferences provide more than education. They provide early insight into where regulatory expectations, governance standards, and financial oversight are evolving, and where scrutiny is likely to increase. Those insights, when acted upon, can strengthen organizations long before issues surface.

Across conferences, jurisdictions, and roles, one conclusion is clear. The captives and RRGs best positioned for long-term stability are those that treat governance as an operational discipline, not a compliance afterthought.

Jennifer Haskell serves as director of regulatory compliance for Risk Services LLC, supporting captive insurers and risk retention groups in navigating complex multi-state regulatory environments. A former state insurance regulator and financial examiner, she brings a regulator’s perspective to governance, compliance and risk management. She regularly works with boards, regulators, auditors, and actuaries to strengthen oversight, documentation, and regulatory credibility. She is a Certified Financial Examiner and Certified Insurance Examiner. She remains actively engaged in regulatory education and notes that the Society of Financial Examiners has approved education provided by all state captive insurance associations for continuing regulatory education.