Insuring High-Profile Clients: A Practitioner's Q&A on Target Risks

The following is adapted from the first episode of the Monoline Exchange webinar series, featuring Will Steck, SVP and Partner in the Private Client Group at CCIG, in conversation with host Janessa Vanderheyden, Senior Training & Partner Education Specialist at Monoline. View the full recording of the webinar here:

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High-profile individuals — athletes, entertainers, executives, politicians — represent one of the most nuanced and consequential segments in personal lines insurance. Their elevated exposures go beyond assets and lifestyle, touching on reputational dynamics, digital presence, and the court of public opinion. In this conversation, Will Steck, who has spent more than five years specializing in coverage for pro athletes and other high-profile clients, draws on a unique background shaped by competitive hockey and experience in high-end hospitality. That perspective informs how he evaluates, presents, and ultimately places complex risks with precision and discipline.

Q: Why are high-profile individuals considered elevated risks in the first place? Is it the lifestyle, the visibility, or something else?

Will Steck: It's both, but more fundamentally, it's a reflection of how society relates to public figures. When we evaluate target risks, we look at the tangibles: occupation, public presence, asset base, family dynamics, reputation. But what we're really insuring against isn't just exposure on paper but the reactions and behaviors of other people.

What we're really insuring against isn't just exposure on paper but the reactions and behaviors of other people.

We put public figures on pedestals. When they reflect our values and aspirations, we hold them to unrealistic standards. And the moment they fall short, the backlash can feel personal. That's when people start looking for reparation. Layer on top of that the widespread perception that these individuals have significant wealth, and the calculus shifts from emotional to opportunistic. Personal injury attorneys are very much part of that equation. There's a belief that there’s not only money to be recovered, but pursuing it often feels justified.

Janessa Vanderheyden: And I think what's changed dramatically is the social media dimension. It used to be that evaluating a high-profile client meant looking at their assets and their properties. Now you're parsing Instagram, TikTok, Facebook…their entire digital footprint. That's an added layer of visibility that didn't exist in the same way even ten years ago. It's not just what they own or where they live anymore but also who they're interacting with, how they engage with fans, what they're amplifying publicly. It continues to evolve, and it has to be part of how we assess these risks holistically.

Will Steck: Absolutely, reputational risk is one of the biggest issues people with a public profile face today, and social media only accelerates it. One wrong association, one controversial statement, and it can affect whether someone gets the next role, the next contract, the next opportunity. That's where the real financial risk often emerges.

Q: What are the most distinct exposures you encounter with this client segment?

Will Steck: A few stand out. First, asset and legal structure. High-profile individuals often have a lot of people in their orbit — talent agents, business advisors, wealth managers — but that doesn't mean they're well-structured. Unlike generational wealth families who typically hold assets in trust with layered liability deferral through entity ownership, many high-profile clients own assets directly. That's significant exposure.

Cyber is another major one, and it's only growing. Deepfakes, generative AI, and account hacking are real threats and the downstream legal and reputational consequences can be severe. How much cyber risk a client carries varies by how active they are digitally. NHL players tend to be pretty quiet on social media, which gives us more room to push back on libel and slander exclusions on umbrella forms. But a TikToker or politician whose brand lives online is a very different story.

Finally, there's the financial risk that doesn't get enough attention. Not every professional athlete is making generational money. League minimums aren't massive, careers are short, and post-career planning is often minimal. A catastrophic loss — property or casualty — can be genuinely financially destructive for someone whose earning window is already closing. Getting limits right matters enormously.

Q: What does strong pre-underwriting actually look like for this segment, and why does it matter so much?

Janessa Vanderheyden: This is something I feel strongly about, having come from the underwriting side. When an agent does the work to truly know their client — not just what's on the application, but the full picture — it completely changes the dynamic with the carrier. You're not just submitting a risk; you're making a case. You're saying, here's who this person is, here's what we might find, and here's why I already know about it. That transparency builds credibility and opens a much more productive line of communication with underwriters.

The principle we come back to is: better risk, better partner. The more complete and honest your submission, the more your carrier partners respect you and the more willing they are to work through the harder placements with you over time.

Better risk, better partner. The more complete and honest your submission, the more your carrier partners respect you and the more willing they are to work through the harder placements with you over time.

Will Steck: And it takes real relationship-building with the client to get there. People with a public profile can get defensive. They want to know why you're asking about their family structure, their loss history, their philanthropic involvement. But those questions are getting at something specific: layers of humility and groundedness. A client who has family, community ties, and genuine reputational stakes behaves differently, and underwriters notice. The pitch should present the whole person, not just the public figure, but the parent, the community member, the off-season version of that person.

When clients are hard to reach (and they often are) Google is your best friend. Public records, award nominations, college history, archived coverage: a lot of it is accessible if you dig past page one. If there are still gaps, flag them as subjectivities. Be transparent about what you know and why you believe this is a strong risk. Half-truths or vague submissions lead to declinations.

Janessa Vanderheyden: I think our industry moves fast, and it's easy to get into a rhythm of: review this, get it out for terms, review the next one. But sometimes you have to slow down and actually put in the work. The thoroughness pays off for the client, for your carrier relationship, and ultimately for you.

Our industry moves fast, and it's easy to get into a rhythm of: review this, get it out for terms, review the next one. But sometimes you have to slow down and actually put in the work.

Q: You mentioned coaching yourself as part of the process. What do you mean by that?

Will Steck: It's easy to get swept up in working with a recognizable name. The excitement of being in front of someone you've admired, or the appeal of a large premium. But you have to be careful. If someone has red flags, the right answer might be to walk away, or to be honest with them about where they need to get to before you can place coverage for them properly. That's not always what they want to hear, but it protects you, your carrier partners, and ultimately the client. You're coaching them toward a place where the coverage can actually do what it's supposed to do.

Janessa Vanderheyden: And it's genuinely easy to get caught up in that excitement. I think anyone in this business would admit that. Which is exactly why it's worth naming it. Recognizing it in yourself gives you the discipline to ask the hard questions anyway.

Q: In today's harder market, how do you approach excess and umbrella layering for clients who need significant limits?

Will Steck: Step-stoning. If a client has no umbrella history, jumping straight to $15 million probably isn't going to fly. You start where the underwriter is comfortable — maybe $5 million — and build the case at each renewal. Every year, you re-present: here's where their assets stand, here's what their lifestyle looks like, here's why the next increment is warranted.

It's also a conversation about premium tolerance versus risk tolerance. Not everyone needs $50 million in coverage just because they have $50 million in net worth. Lifestyle matters. A client who lives quietly, travels modestly, and stays out of controversy is genuinely a different risk than one who doesn't.

When admitted markets have limits, E&S can fill gaps, but you have to read the forms carefully. Exclusions matter, and some excess carriers have specific carve-outs for high-profile athletes or entertainers that could leave a client exposed if not flagged at submission.

Janessa Vanderheyden: And this is where being organized and over-prepared as an agent really shows. The agents who succeed in E&S placements have done the groundwork. When you walk into those markets prepared, you're not asking the underwriter to take a leap of faith. You're giving them a reason to say yes.

Q: How do you help clients think through coverage limit decisions?

Will Steck: I always bring it back to the sleep-at-night standard. But to get there with precision, you need to understand their actual financial exposure: not just their net worth, but what's truly at risk if they were personally sued. That means looping in their attorney, understanding the legal structure, knowing what assets are held individually versus under entity or in trust. The goal is to identify the real floor of personal exposure, then calibrate limits accordingly.

State-level litigation environments matter, too. Average verdict sizes vary dramatically across jurisdictions. In Colorado, for example, average personal litigation settlements are running around $4.95 million right now, which raises legitimate questions about how to prioritize coverage above that threshold.

And here's the upside of bringing in those other advisors: when you loop in a client's wealth manager or estate planning attorney, you're not just helping the client. You're also building relationships with professionals who have other clients who need exactly what you do. It comes full circle.

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The Monoline Exchange is an ongoing webinar series for insurance professionals. Will Steck can be reached through CCIG's Private Client Group.