Brilliance in Focus: Aon 2026 Captives Power Broker Sam Tashima

"Captives have the benefit of being a long-term financial tool for their organizations and are very purpose-driven."
By: | August 19, 2026
Topics: 2026 Power Broker | Brilliance in Focus | Captives | Jan./Feb. 2026 Issue

 

As part of covering the best brokers in the commercial insurance space, Risk & Insurance®, with the sponsorship of Philadelphia Insurance Companies, is expanding its coverage of Power Broker® winners and finalists with its Brilliance in Focus series.

Look for these expanded profiles on the Risk & Insurance website and in your social media feeds throughout the year.

Here we talk to Sam Tashima, head of cyber risk consulting and analytics at Aon and a 2026 Captives Power Broker.
Risk & Insurance: What is the most creative captive structure you’ve designed to solve a client’s ‘uninsurable’ problem, and why was it a career milestone for you?
Sam Tashima: I’m particularly proud of assisting my clients solve a distinct issue related to the insurability of the risk. Whenever I’m dealing with captives and insurance program design, I come back to the adage: “What is the issue we’re looking to solve?” These captive structure examples were issues in which the commercial market was either unable or unwilling to underwrite the risk to a level where we had actuarially quantified the risk.
In those situations, the captive was able to operate as the underwriter of choice for the parent and solve a significant business issue that the parent was facing. I’ve seen this come across with Loss Portfolio Transfers, Medical Stop Loss costs, Cyber hard market (2020-2022), and emerging risks such as Intellectual Property and Artificial Intelligence.
R&I: How did you build your expertise in this complex niche, and what advice do you give younger brokers intimidated by the financial engineering involved?
ST: Across my different actuarial and captive clients, my experience and expertise within captive insurance came through repeated exposure and asking clarifying questions. With any new domain, we’re always starting as relative novices. I’ve always prided myself on asking the basic or clarifying question versus being afraid to ask what may be seen as a naïve or simple question. My goal was always to learn and to accelerate that learning as much as possible. I’ve also been fortunate to have many mentors and patient colleagues who have helped me understand some of the esoteric nuances of coverage terms or captive regulations.

R&I: Unlike traditional policies that bind and roll annually, captives require multi-year governance, board meetings, and ongoing claims oversight. How do you structure your work schedule so that the long-term, continuous management of client captives doesn’t swallow your personal life?

ST: Captives have the benefit of being a long-term financial tool for their organizations and are very purpose-driven. Certain organizations may utilize their captives for a handful of insurance policies whereas others may place north of 15 different policies over the course of a given year. The flexibility surrounding the many insurance uses of a captive can create an always-on cycle, but I view that more as a net benefit to the organization. The existence of such a versatile insurance tool allows the risk manager to think about their insurance purchasing strategy throughout the course of a year versus just once or twice a year. For the captives where I’m the opining actuary, we place a heavy emphasis on processes surrounding project flow so that we’re on top of timing requirements for various deliverables from premium projections to reserve analyses.

R&I: What is the off-the-clock activity or daily routine that allows you to step away from balance sheets and maintain long-term mental sharpness?

ST: Two daily routines that keep me grounded are my morning exercise routine before the workday and my daily 30+ minute ruck/hike. I’ve found that keeping my body actively engaged helps keep my mind sharp throughout the day. In particular, I love my outdoor hikes as I’m able to achieve both physical and cognitive benefits by unplugging and providing a mental reset from the day. &

Elisa Ludwig is a contract writer based outside Philadelphia. She has written extensively about cybersecurity issues for the Junto blog on the eRiskHub. She can be reached at [email protected].