Rising Star Jason Bosley on the Importance of Communication and Team-Building

For Jason Bosley, director of risk & broking at Willis Towers Watson, long-term success in the dynamic and challenging financial services sector means assembling a team he can count on to deliver support.
By: | August 23, 2023
Portrait of Jason Bosley

Come see the Stars! As part of our ongoing coverage of the best brokers in the commercial insurance space, Risk & Insurance®, with the sponsorship of Philadelphia Insurance, is expanding its coverage of the Rising Stars, those brokers who represent the next wave of insurance brokering talent.

Look for these expanded profiles on the Risk & Insurance website and in your social media feeds throughout 2023.

Here’s our conversation with Jason Bosley, director of risk & broking at Willis Towers Watson and a 2023 Finance Power Broker winner.

Risk & Insurance: To start, tell us about your career journey into insurance and how you came to your current role.

Jason Bosley: I began my career in insurance in March of 2009 when I joined Travelers as a management liability underwriter in the bond and financial products unit. My background, focus and determination allowed Travelers to insert me as an underwriter within their financial institutions practice. At that time, the U.S. was experiencing a deep recession, and I learned very quickly how to consistently communicate and deliver challenging messages to our clients.

After growing in that role for a few years, I realized that I had an innate ability to be in front of and communicate directly with clients, structuring risk management solutions and building long-term partnerships. With a strong belief in myself, I left the underwriting side to become a producer in March 2013. Since 2013, I have thoroughly enjoyed the production role and the opportunities it has afforded me both professionally and personally. My experience at WTW has challenged me and continually forces me to grow as a producer; the sky is the limit.

R&I: What are the biggest challenges facing financial services brokers and their clients right now? 

JB: I believe there are ongoing challenges that we face in the financial services arena that we must continually adapt to. The marketplace continues to be dynamic.

Over the last few years, we have seen major swings within the insurance environment that have put pressure on financial institutions. These swings include significant rate and capacity pressure in property, excess liability, professional E&O and cyber. Add in inflationary pressures and continued supply chain issues, and our clients have had to be very strategic in how they approach their risk management programs.

While the cyber market has “improved” from a rate standpoint, there are still challenges that our clients face daily, as hackers are continually finding new ways to breach systems and impact the world we live in.

Lastly, the current macroeconomic environment is a challenge all of our clients are dealing with. We have seen the impact that rising interest rates can have in the FI space, and the continued scrutiny on proper capital adequacy and increased regulatory pressure creates a unique environment. This is the basis of why our clients must be proactive in their risk management approach.

R&I: What new and emerging risks are you seeing in the financial industry? How are your clients preparing? 

JB: Our clients continue to see emerging risks in the form of old ones with a new face, or those risks that continue to evolve — specifically, artificial intelligence, cybersecurity implications, ESG/climate risk and increased regulatory scrutiny.

To assist our clients in navigating these “new waters,” we talk about enhanced IT controls and proactive cyber hygiene, providing financial institutions with dedicated industry resources and personnel, and the development of intricate real-time analytics that assist in managing complex risks, including climate, cyber and ESG.

R&I: What is your brokering philosophy and how do you apply that in your day-to-day? 

JB: I have always taken pride in striving for service excellence. This includes listening to clients’ needs and being proactive and very responsive on a day-to-day basis. Our clients rely on us to provide them with guidance, resources and expertise, and lack of responsiveness is unacceptable. Their job is to run their business and have enough trust in us that we have their back, and that we will take care of any issues that arise and manage their risk management programs proactively each year.

R&I: How do you stay focused when working with large clients and the complexities of their accounts? 

JB: My focus is squarely based on the trust and reliance of the team put in place to service our large clients. My approach is to set all parties up for success; this is why the team approach is important to me. I concentrate on being the strategic leader of the team, making sure they understand the service needs and strategic objectives of the client so they can execute on those strategies.

The beauty of this approach is that it allows the team to embrace success and provide our clients with the dedicated expertise that is needed, whether it pertains to M&A activity, a challenging renewal given the marketplace or day-to-day operations. No one person can do it alone on large deals, so the team is the most critical part.

R&I: What advice do you have for new brokers starting in the industry? 

JB: One of the best pieces of advice that I received as a young producer was that you can’t do it alone. You may be able to “grind it out” for a couple of years and have some success, but long-term success requires a team approach. This was the best advice I could have received as a young producer trying to navigate building a book of business. I would employ that same advice today.

Don’t go at it alone! Lean on those around you and let their success be your success. Listen and learn, know what you don’t know, and trust others to provide you with the support necessary to be successful. In the long run, I think, you will be more respected by your clients and colleagues. &

Abi Potter Clough, MBA, CPCU, is a keynote speaker, author and business consultant focused on Insurtech, leadership and strategy. She has over 15 years of experience at a Fortune 500 company with expertise in P&C claims operational leadership, lean management consulting, digital communications and Insurtech. As the past chair of the International Insurance Interest Group of the CPCU Society, Abi remains involved in many international initiatives and projects. She has published two books about change management and relocation. Abi can be reached at [email protected].

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