Defining Moments Behind My Underwriting Leadership
First and most impactful have been the mentors I’ve had throughout my career. From the very beginning to my current role, I’ve had the privilege of working alongside exceptional leaders who have shaped both my professional development and my approach to leadership. A few call outs here are Costas Hadjipateras, Christina Wong, Patrick Wong, and Justin Levine.
In addition to my mentors, two key experiences stand out:
First was my early experience in underwriting large complex casualty accounts. I worked in the US and in Hong Kong on large multinational casualty programs that had a lot of moving parts. Underwriting complex exposures in different legal systems, and litigation environments was definitely an accelerator for my early development as an underwriter. Then getting exposure to national accounts with broader relationships than my individual product helped me gain a big picture view and take into consideration more than just the individual metrics on any one deal.
The second has been building and leading teams here at Shepherd. Having the opportunity to be a part of building the book of business and growing a team here has had a major impact on my personal development. When I first joined, we had 2 policies in force and only 3 underwriters including myself. Initially my focus was on unlocking distribution, and producing high quality business. As the company grew I was given an opportunity to open our New York office and build out a team. That was a major growth point for me. I’d always been a strong individual production underwriter, but training others to do the same is a totally different skillset.
What I learned quickly is that leadership is much more about people than production. As an individual contributor, you control the outcome. As a leader, your job is to create clarity, build confidence, and remove obstacles so others can perform at a high level. That means investing time in coaching, walking through live deals, explaining not just what decision we made but why we made it, and helping underwriters develop their own risk judgment.
The biggest growth for me has been shifting from “How do I win this account?” to “How do I help ten other people win consistently?” Watching younger underwriters build confidence, develop broker relationships, and take ownership of their books has been one of the most rewarding parts of my career.
Balancing Data and Judgment in Risk Assessment
Data is essential in underwriting, but it’s not definitive.
The common thread across all of this is discipline.
At Shepherd, we think of data as providing signals. It gives us direction, highlights trends, and pressures assumptions. Loss development, trend factors, exposure analytics all form the scientific foundation of the decision. If the data doesn’t support a risk structurally, we don’t try to “out-judge” it.
But underwriting has always been more than math.
Two projects can model similarly and perform very differently based on qualitative factors like contractor culture, jurisdictional environment, and risk management controls in place. That’s where judgment comes in. Data can tell you what has happened and what is likely. It cannot fully capture how a risk will behave under stress.
One area where we’ve leaned into this balance is through our Shepherd Savings program. We actively analyze construction technology data, from onsite reality capture to project management platforms to better understand how contractors are managing risk in real time. When we see meaningful investment in safety-enhancing technology, we reflect that in our underwriting approach.
The philosophy is simple: let technology handle the science side of underwriting so our team can focus on the art. We equip our underwriters with strong analytics and objective signals so the foundational work is done consistently. That allows them to focus on the art by asking better questions, understanding structural nuance, and exercising informed judgment.
The balance isn’t about choosing one over the other. It’s about sequencing them properly. Science first. Judgment second. Discipline always.
Navigating Today’s Underwriting Challenges
There are three major challenges underwriting teams are navigating in today’s market.
First, severity volatility - particularly in casualty. Social inflation, nuclear verdicts, and expanding legal theories have fundamentally changed the loss landscape. Historical data alone is no longer a reliable predictor of future outcomes. Underwriters have to price for forward-looking risk, not backward-looking averages.
Second, capital fluidity. Markets can tighten quickly, but they can also soften just as fast. Competitive pressure builds rapidly, and the temptation to stretch on structure or pricing is real. The challenge for underwriting teams is maintaining discipline when others are chasing volume. Long-term performance is almost always determined by the decisions made in softer markets.
Third, complexity. Risks themselves are becoming more sophisticated with larger and lengthier projects, multi-layered stakeholder involvement, and expansion into emerging markets. At the same time, underwriting teams are expected to operate on tighter timelines. The balance between speed and depth has never been more important.
The common thread across all of this is discipline. Teams that succeed in this environment are the ones that combine strong analytics, clear appetite, and cultural alignment around risk tolerance. Markets will cycle. Volatility will persist. What matters most is whether your underwriting framework holds under pressure.
