Raising the bar at CICA
At this year’s Captive Insurance Companies Association conference (CICA), few speakers will be as busy as Rob Walling, principal and consulting actuary at Pinnacle Actuarial Resources. Walling is taking on the unusual distinction of presenting two separate sessions.
One of those sessions forms part of CICA’s newly created regulators-only track, an initiative designed to provide a dedicated forum for captive insurance regulators. Walling will join Kim Guerrero of Milliman in the presentation, “Actuarial Feasibility Studies for Domicile Regulators: Essential Insights and Best Practices for Captive Insurance Oversight” on Tuesday, March 10 at 9:00-9:50 a.m. to explore what regulators should expect when reviewing captive feasibility studies and actuarial reports.
The focus will not simply be on best practice. Around half of the session will address positive indicators in actuarial work products – the hallmarks of robust methodology, transparent assumptions and well-supported conclusions. The remainder will concentrate on warning signs. These are not necessarily glaring errors, but subtler red and yellow flags: elements that may appear innocuous at first glance yet signal deeper issues in data quality, modelling or governance.
For Walling, the opportunity is particularly meaningful because the panel was selected by regulators themselves. Being identified as an actuary they want to hear from, he says, is a considerable honour. It also reflects the day-to-day reality of his firm’s work. Pinnacle frequently engages directly with regulators, helping to explain actuarial approaches and clarify technical findings. Having many regulators gathered in one place creates a rare chance for candid, constructive dialogue about expectations on both sides of the table.
If the regulators’ session is grounded in technical rigour, Walling’s second presentation, “Advocacy Matters: Captive Support of Parent Mission” on Monday, March 9 at 3:30-4:20 p.m. takes a broader and more philosophical turn. Joined by Heather McClure of Helio Risk, Kevin Doherty of Dickinson Wright and David Beyer of Alaska Airlines, he will examine how captives can support advocacy and advance the social mission of their parent organisations.
The premise is straightforward yet powerful: captives are about more than risk financing. While they provide control over insurance programmes and greater strategic flexibility, they can also be structured to reinforce an organisation’s core values and social objectives.
Walling offers a striking example. He is currently involved in a programme for investigative journalists around the world. A captive has been established in Vermont to provide defence coverage for journalists who may face legal action as a result of their reporting. In a climate where investigative work can attract significant pressure and risk, the captive becomes a practical tool for safeguarding press freedom.
Other illustrations span very different sectors. Religious institutions, universities and hospitals may also find that their insurance structures can reflect their underlying commitments, whether to community health, education or faith-based service.
Sometimes, the catalyst is intensely personal. Walling recounts a situation in which a senior employee’s spouse survived a life-threatening medical emergency requiring dozens of blood transfusions. The experience galvanised the entire company around blood donation, inspired by the life-saving work of the American Red Cross. In cases like this, a business’s advocacy priorities may not be obvious from its balance sheet, yet they become woven into its corporate DNA.
Captives can play a role in that evolution. Walling has worked on structures supporting in vitro fertilisation access, insurance for surrogate mothers and innovative approaches to PTSD treatment, including psychedelic micro-dosing. He is currently involved in efforts to make gene therapies for conditions such as sickle cell disease more financially viable. With some treatments priced in the millions, insurance design becomes central to ensuring patients can benefit from scientific breakthroughs.
For an actuary, these assignments go beyond the stereotypical “maths and graphs”. They demand technical precision, certainly, but they also offer the satisfaction of contributing to programmes with tangible social impact. Walling describes this as an energising departure from purely numerical exercises: a reminder that actuarial science can underpin meaningful change.
Beyond his own sessions, Walling is emphatic about the importance of CICA itself. For captive professionals, he regards it as essential. In his view, there are only a handful of conferences each year that are truly unmissable, and CICA sits firmly in that elite category. It is the first major gathering of the year at which managers, regulators, owners and service providers converge in significant numbers.
This concentration of “heads of state”, as Walling puts it, gives the conference a distinctive character. High-calibre educational sessions are matched by equally valuable informal exchanges. For a firm such as Pinnacle, the event is an opportunity not only to contribute thought leadership but also to reconnect with clients and long-standing partners.
Set against the backdrop of Palm Springs, the conference may offer attractive surroundings, but its real draw lies in the quality of engagement. Whether discussing technical red flags in actuarial reports or the transformative potential of advocacy-driven captives, Walling’s dual roles this year capture the breadth of a sector that continues to evolve.
From regulatory scrutiny to social purpose, the captive industry is expanding its horizons. And at CICA, those conversations will be front and centre.
Advocacy Matters: Captive Support of Parent Mission | Monday, March 9 at 3:30-4:20 p.m.
Actuarial Feasibility Studies for Domicile Regulators: Essential Insights and Best Practices for Captive Insurance Oversight | Tuesday, March 10 at 9:00-9:50 a.m.
Rob Walling will also be co-hosting a Pinnacle APEX Webinar discussing the topic of advocacy in captives on March 19, 2026 at 2 p.m. (Eastern). You can register here.
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