84 Insurance Brokers You Haven’t Heard the Last Of

United by their award-winning brokering skills, these young professionals are showing the world what it takes to succeed in the insurance space.
By: | May 15, 2020

Every year, Risk & Insurance® recognizes the best of the best in insurance brokering.


These Power Brokers exemplify creative risk solutions, exceptional customer service and a profound knowledge of the industry across 29 sectors. This year, 190 brokers were named as 2020 Power Broker® winners and finalists.

Of these, 84 winners and finalists were under the age of 40, making them Risk & Insurance Rising Stars.

In an industry ripe with possibility, Rising Stars have carved out a place for themselves early in their careers. They are recognized for their passion for the industry and doing the right thing for their clients.

“I enjoy solving complex issues for my clients,” said Will Wilson, Jr., age 27, risk adviser and partner, McNeal, Sports & Wilson Risk Advisers.

In Wilson’s view, the general public tends to have a negative perception of what insurance actually does. So, for Wilson, an At-Large Power Broker, finding clients with problems to solve and then solving them in a way that shows the value of the industry motivates him: “It’s the gas to my engine,” he said.

Will Wilson Jr., risk advisor | partner, McNeal, Sports & Wilson

For other Rising Stars, the drive to perform well for their clients comes from an inherent desire to help others succeed. Emily Weiss Schaffer, age 34, said, “I want to be good at the job I do. I take pride in the work I do, and to have clients value what I do for them is invaluable.”

Schaffer, a Fine Arts Power Broker and senior account executive at DeWitt Stern, a division of Risk Strategies, doesn’t want insurance to ever be the obstacle in her clients’ way.

“I never want insurance to hold something up or prevent a piece from getting into an exhibition,” she said.

“In the art world, there are a lot of moving pieces, and insurance tends to be the last thing on the clients’ minds.”

The Road to Becoming a Power Broker

What really sets these Power Broker Rising Stars apart is their need to build relationships that last.

“Brokering requires a number of skills — a mixing of people skills with analytical thinking — particularly when dealing with high-profile clients in C-suites at large companies,” said Clare McCarrick, senior associate at Willis Towers Watson.

Read More: Introducing the 2020 Power Broker® Rising Stars

In 2019, McCarrick was instrumental in placing coverages related to one of the largest IPOs in U.S. history. At just 29 years old, this Finance Power Broker worked tirelessly to get the coverage her clients needed, utilizing analytics and communicating her findings with her clients.


She built trust with her clientele, letting the data she collected illuminate areas in need of improvement and demonstrating the potential advantages of alternative program structures.

“The fun part [of the job] is meeting the people, seeing the support systems in place and developing a unique relationship with those in the industry,” she said.

For Wilson, his clients see exactly what a good relationship can bring: the best results. He became a Power Broker by going the extra mile to secure improved coverage and save his clients thousands of dollars in premiums.

Digging down deep into four years’ worth of historical payroll and claims data, Wilson was able to immediately reduce overall premium spend by 16% and future term premium spend by 27% for one client.

“I saw what they wanted to achieve, and I wanted to show I could get that for them,” he said. “I try to go above and beyond, because I want my clients to view me as an investment, rather than an expense.”

Schaffer, too, builds relationships that last. Her proactive nature is what keeps her clients ahead of growing risks in the fine arts industry. Last year, she noticed several ADA claims were coming in against shop owners and other retail venues as the public demanded accessibility for those with disabilities.

“Galleries could be hit hard with a claim if they didn’t have ramps leading into the main entrance,” she explained. So, she sent an email to her clients and discussed the ways in which each could be better compliant with ADA regulations. EPLI coverage or updating their websites were just two items they discussed.

Entering into insurance, “I learned that I could carve out a space for myself in art and advocate for these clients,” Schaffer added. “The longer one works in the industry, the stronger relationships grow.”

Always Staying Proactive

Although they have great accomplishments already under their belts, these young professionals are just getting started. McCarrick, Schaffer and Wilson all attest to the benefit of keeping themselves up-do-date on the latest goings-on in their respective industries.

Emily Weiss Schaffer, senior account executive, DeWitt Stern

McCarrick said that she tries to read as many insurance publications as she can to keep up on the macro-economic trends impacting financial lines.

Schaffer, likewise, likes to read the news and share articles with her internal team as well as her clients on insights that might be relevant to the art world.

“Staying active in a client’s industry is a team effort,” she explained. “We ask each other questions, and we share our information.”

“I had a mentor tell me once, ‘Don’t tell your client you’re in the insurance industry, tell them you’re in their industry,’ ” Wilson said of his approach.

With that in mind, Wilson has made it a mission to join the associations that his clients are in, alongside getting active in those organizations.

“We keep current of the lobbyists who are trying to improve statutes for the industries our clients work in. We try to stay in front of legislation that could impact them,” he said.

Combating a Rising Talent Gap

Staying ahead of emerging risks doesn’t stop with clients, however. With 84 Rising Stars this year, it’s hard to believe that the insurance industry is facing the risk of a talent shortage in the coming years.


Yet, this is the unfortunate truth.

The RIMS’ Risk Management Talent 2025 report released in September 2019 found that only 16% of respondents think there will be enough graduates to fill open positions in the risk and insurance space by 2025. Couple this with the vast majority of baby boomers retiring in the next five to ten years — it’s a recipe for a huge workforce shortage.

Or, perhaps, a recipe for success.

“Between the current group of leadership in brokerages, agencies and even the carrier space, there is a huge gap in age. And that’s ripe with so much opportunity for young people to come in,” Wilson explained. “There’s a need for young folks in, arguably, every silo of the industry.”

Wilson’s connection to insurance is in his blood, having been born into a family that operates its own smaller insurance firm. Although he has since moved on from that firm, the advantage of seeing the industry from the inside at such a young age enabled him to recognize the opportunity awaiting a young professional looking to make a place for themselves.

And getting students interested in insurance starts with awareness.

Clare McCarrick, senior associate, Willis Towers Watson

“I love my job and am excited to come in every day,” said Wilson. Young insurance professionals, he said, need to get involved early. “A lot of those who are successful worked under the guidance of someone else.”

This is why Wilson makes a concerted effort to mentor a risk management and insurance student each semester at the University of Georgia. He makes himself available for speaking as well as mentoring and talking to individual students pursuing a risk management and insurance degree.

“We have to be the ambassadors for our industry, because a lot of young folks don’t understand what we do. Insurance isn’t going away, so it’s crucial for us to help others understand what we do.”

McCarrick echoed Wilson. “Creating mentor groups and seeing organizations help people thrive is an encouraging sight,” she said.


Schaffer has also spoken during lectures at colleges, particularly with art history and studio students, as well as those in the business track.

Part of why Schaffer loves what she does is that it keeps her in tune with the art world. Formerly an art history/studio major herself, insurance has enabled her to advance her career while keeping her involved in the industry she loves.

“I get to meet fascinating people in the field. I’ve met major living artists and talked about how to protect their life’s work. I’ve seen their art studios and galleries and the projects they’re working on, and I get to help make them come to life.”

That is the best part of insurance for her; being able to take her passion and make it a reality. She believes that is what young professionals need to know: “It’s important for us already in the industry to educate students on their potential career path. Especially students who aren’t an obvious ‘choice’ for the industry, like art majors.” &

Rising Stars are winners and finalists in Risk & Insurance®’s Power Broker® award competition, all of whom were under the age of 40 as of the Power Broker® publication date of Feb. 24. Since the launch of this designation in 2014, more than 450 brokers have been so recognized.

Risk & Insurance® celebrates these Rising Stars, as sponsored by The Hartford, for their achievements and for their emerging role as leaders of the commercial insurance industry. The recognition honors their creativity, exceptional customer service and industry knowledge in finding solutions for their clients.

To view the full list of 2020 Power Broker Rising Stars, visit here.

Autumn Heisler is the content strategist at Risk & Insurance®. She can be reached at [email protected]

More from Risk & Insurance

More from Risk & Insurance

Risk Scenario

The Betrayal of Elizabeth

In this Risk Scenario, Risk & Insurance explores what might happen in the event a telemedicine or similar home health visit violates a patient's privacy. What consequences await when a young girl's tele visit goes viral?
By: | October 12, 2020
Risk Scenarios are created by Risk & Insurance editors along with leading industry partners. The hypothetical, yet realistic stories, showcase emerging risks that can result in significant losses if not properly addressed.

Disclaimer: The events depicted in this scenario are fictitious. Any similarity to any corporation or person, living or dead, is merely coincidental.


Elizabeth Cunningham seemingly had it all. The daughter of two well-established professionals — her father was a personal injury attorney, her mother, also an attorney, had her own estate planning practice — she grew up in a house in Maryland horse country with lots of love and the financial security that can iron out at least some of life’s problems.

Tall, good-looking and talented, Elizabeth was moving through her junior year at the University of Pennsylvania in seemingly good order; check that, very good order, by all appearances.

Her pre-med grades were outstanding. Despite the heavy load of her course work, she’d even managed to place in the Penn Relays in the mile, in the spring of her sophomore season, in May of 2019.

But the winter of 2019/2020 brought challenges, challenges that festered below the surface, known only to her and a couple of close friends.

First came betrayal at the hands of her boyfriend, Tom, right around Thanksgiving. She saw a message pop up on his phone from Rebecca, a young woman she thought was their friend. As it turned out, Rebecca and Tom had been intimate together, and both seemed game to do it again.

Reeling, her holiday mood shattered and her relationship with Tom fractured, Elizabeth was beset by deep feelings of anxiety. As the winter gray became more dense and forbidding, the anxiety grew.

Fed up, she broke up with Tom just after Christmas. What looked like a promising start to 2020 now didn’t feel as joyous.

Right around the end of the year, she plucked a copy of her father’s New York Times from the table in his study. A budding physician, her eyes were drawn to a piece about an outbreak of a highly contagious virus in Wuhan, China.

“Sounds dreadful,” she said to herself.

Within three months, anxiety gnawed at Elizabeth daily as she sat cloistered in her family’s house in Bel Air, Maryland.

It didn’t help matters that her brother, Billy, a high school senior and a constant thorn in her side, was cloistered with her.

She felt like she was suffocating.

One night in early May, feeling shutdown and unable to bring herself to tell her parents about her true condition, Elizabeth reached out to her family physician for help.

Dr. Johnson had been Elizabeth’s doctor for a number of years and, being from a small town, Elizabeth had grown up and gone to school with Dr. Johnson’s son Evan. In fact, back in high school, Evan had asked Elizabeth out once. Not interested, Elizabeth had declined Evan’s advances and did not give this a second thought.

Dr. Johnson’s practice had recently been acquired by a Virginia-based hospital system, Medwell, so when Elizabeth called the office, she was first patched through to Medwell’s receptionist/scheduling service. Within 30 minutes, an online Telehealth consult had been arranged for her to speak directly with Dr. Johnson.

Due to the pandemic, Dr. Johnson called from the office in her home. The doctor was kind. She was practiced.

“So can you tell me what’s going on?” she said.

Elizabeth took a deep breath. She tried to fight what was happening. But she could not. Tears started streaming down her face.

“It’s just… It’s just…” she managed to stammer.

The doctor waited patiently. “It’s okay,” she said. “Just take your time.”

Elizabeth took a deep breath. “It’s like I can’t manage my own mind anymore. It’s nonstop. It won’t turn off…”

More tears streamed down her face.

Patiently, with compassion, the doctor walked Elizabeth through what she might be experiencing. The doctor recommended a follow-up with Medwell’s psychology department.

“Okay,” Elizabeth said, some semblance of relief passing through her.

Unbeknownst to Dr. Johnson, her office door had not been completely closed. During the telehealth call, Evan stopped by his mother’s office to ask her a question. Before knocking he overheard Elizabeth talking and decided to listen in.


As Elizabeth was finding the courage to open up to Dr. Johnson about her psychological condition, Evan was recording her with his smartphone through a crack in the doorway.

Spurred by who knows what — his attraction to her, his irritation at being rejected, the idleness of the COVID quarantine — it really didn’t matter. Evan posted his recording of Elizabeth to his Instagram feed.

#CantManageMyMind, #CrazyGirl, #HelpMeDoctorImBeautiful is just some of what followed.

Elizabeth and Evan were both well-liked and very well connected on social media. The posts, shares and reactions that followed Evan’s digital betrayal numbered in the hundreds. Each one of them a knife into the already troubled soul of Elizabeth Cunningham.

By noon of the following day, her well-connected father unleashed the dogs of war.

Rand Davis, the risk manager for the Medwell Health System, a 15-hospital health care company based in Alexandria, Virginia was just finishing lunch when he got a call from the company’s general counsel, Emily Vittorio.

“Yes?” Rand said. He and Emily were accustomed to being quick and blunt with each other. They didn’t have time for much else.

“I just picked up a notice of intent to sue from a personal injury attorney in Bel Air, Maryland. It seems his daughter was in a teleconference with one of our docs. She was experiencing anxiety, the daughter that is. The doctor’s son recorded the call and posted it to social media.”

“Great. Thanks, kid,” Rand said.

“His attorneys want to initiate a discovery dialogue on Monday,” Emily said.

It was Thursday. Rand’s dreams of slipping onto his fishing boat over the weekend evaporated, just like that. He closed his eyes and tilted his face up to the heavens.

Wasn’t it enough that he and the other members of the C-suite fought tooth and nail to keep thousands of people safe and treat them during the COVID-crisis?

He’d watched the explosion in the use of telemedicine with a mixture of awe and alarm. On the one hand, they were saving lives. On the other hand, they were opening themselves to exposures under the Health Insurance Portability and Accountability Act. He just knew it.

He and his colleagues tried to do the right thing. But what they were doing, overwhelmed as they were, was simply not enough.


Within the space of two weeks, the torture suffered by Elizabeth Cunningham grew into a class action against Medwell.

In addition to the violation of her privacy, the investigation by Mr. Cunningham’s attorneys revealed the following:

Medwell’s telemedicine component, as needed and well-intended as it was, lacked a viable informed consent protocol.

The consultation with Elizabeth, and as it turned out, hundreds of additional patients in Maryland, Pennsylvania and West Virginia, violated telemedicine regulations in all three states.

Numerous practitioners in the system took part in teleconferences with patients in states in which they were not credentialed to provide that service.

Even if Evan hadn’t cracked open Dr. Johnson’s door and surreptitiously recorded her conversation with Elizabeth, the Medwell telehealth system was found to be insecure — yet another violation of HIPAA.

The amount sought in the class action was $100 million. In an era of social inflation, with jury awards that were once unthinkable becoming commonplace, Medwell was standing squarely in the crosshairs of a liability jury decision that was going to devour entire towers of its insurance program.

Adding another layer of certain pain to the equation was that the case would be heard in Baltimore, a jurisdiction where plaintiffs’ attorneys tended to dance out of courtrooms with millions in their pockets.

That fall, Rand sat with his broker on a call with a specialty insurer, talking about renewals of the group’s general liability, cyber and professional liability programs.

“Yeah, we were kind of hoping to keep the increases on all three at less than 25%,” the broker said breezily.

There was a long silence from the underwriters at the other end of the phone.

“To be honest, we’re borderline about being able to offer you any cover at all,” one of the lead underwriters said.

Rand just sat silently and waited for another shoe to drop.

“Well, what can you do?” the broker said, with hope draining from his voice.

The conversation that followed would propel Rand and his broker on the difficult, next to impossible path of trying to find coverage, with general liability underwriters in full retreat, professional liability underwriters looking for double digit increases and cyber underwriters asking very pointed questions about the health system’s risk management.

Elizabeth, a strong young woman with a good support network, would eventually recover from the damage done to her.

Medwell’s relationships with the insurance markets looked like it almost never would. &


Risk & Insurance® partnered with Allied World to produce this scenario. Below are Allied World’s recommendations on how to prevent the losses presented in the scenario. This perspective is not an editorial opinion of Risk & Insurance.®.

The use of telehealth has exponentially accelerated with the advent of COVID-19. Few health care providers were prepared for this shift. Health care organizations should confirm that Telehealth coverage is included in their Medical Professional, General Liability and Cyber policies, and to what extent. Concerns around Telehealth focus on HIPAA compliance and the internal policies in place to meet the federal and state standards and best practices for privacy and quality care. As states open businesses and the crisis abates, will pre-COVID-19 telehealth policies and regulations once again be enforced?

Risk Management Considerations:

The same ethical and standard of care issues around caring for patients face-to-face in an office apply in telehealth settings:

  • maintain a strong patient-physician relationship;
  • protect patient privacy; and
  • seek the best possible outcome.

Telehealth can create challenges around “informed consent.” It is critical to inform patients of the potential benefits and risks of telehealth (including privacy and security), ensure the use of HIPAA compliant platforms and make sure there is a good level of understanding of the scope of telehealth. Providers must be aware of the regulatory and licensure requirements in the state where the patient is located, as well as those of the state in which they are licensed.

A professional and private environment should be maintained for patient privacy and confidentiality. Best practices must be in place and followed. Medical professionals who engage in telehealth should be fully trained in operating the technology. Patients must also be instructed in its use and provided instructions on what to do if there are technical difficulties.

This case study is for illustrative purposes only and is not intended to be a summary of, and does not in any way vary, the actual coverage available to a policyholder under any insurance policy. Actual coverage for specific claims will be determined by the actual policy language and will be based on the specific facts and circumstances of the claim. Consult your insurance advisors or legal counsel for guidance on your organization’s policies and coverage matters and other issues specific to your organization.

This information is provided as a general overview for agents and brokers. Coverage will be underwritten by an insurance subsidiary of Allied World Assurance Company Holdings, Ltd, a Fairfax company (“Allied World”). Such subsidiaries currently carry an A.M. Best rating of “A” (Excellent), a Moody’s rating of “A3” (Good) and a Standard & Poor’s rating of “A-” (Strong), as applicable. Coverage is offered only through licensed agents and brokers. Actual coverage may vary and is subject to policy language as issued. Coverage may not be available in all jurisdictions. Risk management services are provided or arranged through AWAC Services Company, a member company of Allied World. © 2020 Allied World Assurance Company Holdings, Ltd. All rights reserved.

Dan Reynolds is editor-in-chief of Risk & Insurance. He can be reached at [email protected]