Great Leadership in Excess and Surplus Is Essential, According to These Under-40 Professionals

This group of E&S professionals shared their thoughts on how to be most successful and impactful as organizational leaders.
By: | September 26, 2020

Just as water will find its own level, the WSIA panel billed as a forum on leadership was a much more wide-ranging discussion.


The panel was held on Sept. 16 during the virtual 2020 WSIA Annual Marketplace. Hosted by WSIA’s U40, a group made up of E&S professionals under the age of 40, this panel of industry executives shared their thoughts on how to be most successful and impactful as organizational leaders.

The theme that emerged organically was that the broader insurance sector has shown remarkable strength despite near-biblical pandemic, wildfire, flood and recession.

The panel was in agreement that a diversity of background and experience has been essential in their individual careers and also at their companies for surviving — even thriving — in difficult days.

Headwinds and Tailwinds

Amid all the bad news, Davis Moore, chief executive officer of Worldwide Facilities, LLC, and vice president of WSIA, suggested that “this has been a year of both headwinds and tailwinds. The industry is facing something between $25 billion and $200 billion in losses from the pandemic. That is falling particularly on surplus lines. We know that many of our insureds have been forced to close their doors.”

There has also been a heavy impact on carriers and wholesale operations in workers’ compensation, he added.

“The current situation reminds me of the aftermath of Hurricane Rita in 2005,” said Gerald Dupre, Jr., president of specialty property insurance at Hallmark Financial Services. “Hurricane Laura came ashore over Lake Charles [Louisiana], which was unfortunate for that community. The landfall was between two more populous areas to the east [New Orleans] and west [Houston], so we won’t see the widespread devastation in those sectors.”

There was also a sigh of relief off shore. “There were $55 billion worth of oil rigs bracing for losses from Laura,” Dupre added. “In the event, it was not too bad.”

He also noted that it is still hurricane season and still wildfire season in the west. “The seasons seem to be running longer than normal,” Dupre noted.

The most important tailwind that Moore cited is that “we are seeing rate adequacy in many lines for the first time in a while. There is also an inflow of admitted markets and significant opportunities for growth.”

Wendy Houser, regional president at Markel concurred: “There are certainly struggles in the small transactional businesses. We are seeing cancellations and requests for return of premium. But we are also able to see rates that we have not seen in years. Some brokers are seeing double-digit growth.”

It’s a Business of People

Josh Ammons, senior vice president at AmWINS Brokerage, and WSIA U40 past president credited the people in the trenches. “Our clients on the retail side are doing a great job of retaining business.”

“I am starting down a renewal that is going be something like a 20% increase on a seven-figure premium,” Ammons said. “As I was preparing for that, I was also asked by the same client for some idea about how the 2021 renewal might look.


“Earlier in my career I would have been very uneasy about how to tell the client that. At this point, the next renewal is likely to be another 15% to 20%,” he continued. “I would have been afraid that they would just call someone else.”

Instead of the client picking up the telephone, Ammons did. “I’m comfortable calling colleagues, and even competitors — people who I know from my time in the industry and I have met at events — and talking with them before giving the answer to the client.”

Where Leadership Can Grow During Turbulent Times

The panel concurred that individuals and companies have done remarkably well in adapting technology to carry on despite a global public-health disaster. That said, Ammons expressed concern about the loss of interpersonal interaction.

“I know who I know, but I don’t know who I don’t know,” he noted ruefully. “I miss the industry conferences where we have a chance to meet and interact. We’re all proud that we have not skipped beat in our businesses, but I wonder about the newer people who are being sheltered in terms of their interactions around the industry.”

Elissa Kelly, associate vice president at Nationwide E&S/Specialty said that “issues such as those are not always easy to see. It is important to show leadership, not just in working remotely and getting things done, but also in setting the tone at the office when we go back.”

Houser added that insight flows both ways. “Reverse mentorships have been important in keeping me on top of trends.”

Why Good Leaders Are Focused on Recruitment and Developing Talent

Hiring and development are about patience, said Ammons. “It takes time for new people to acquire the technical knowledge necessary to get deals done. A broker’s career is like a hockey stick: It goes along straight and level for years, then just takes off. I encourage people to stay patient, but hungry.”

Houser said the same principle applies to underwriting. “An underwriter may not see the clients for 8 to 10 years. We want our underwriters to be aggressive when it makes sense to be, but not too aggressive in meeting [sales] targets to put the book [of business] or the company at risk.”

Moore extended that logic. “We ask our associates to be specialized, but to grow opportunities you need to broaden your experience. That will increase your value to yourself and to your employer.”

Kelly added, “I started as a claims adjustor in general liability. I urge anyone hiring to focus on diversity, including the balance of hiring for potential versus hiring for expertise.”

Ammons is now at a large property office in Charlotte, North Carolina, after several years in New York. Houser began her career at a small managing general agent before moving into brokerage.

“I was a biology/pre-med major who did not like sick people,” said Dupre with a laugh, “so I went into insurance.”

Like medicine, though, “insurance is a practice,” he said, “it is based on experience. When we start in underwriting we learn to take and check the boxes. Ten years later, we know which boxes are important.”


The panel reflected that they were all fortunate to be in this business. “My first job as a young broker was with the St. Paul under Carl Drake,” Dupre recalled. “He told me, ‘you are choosing a career in a very sustainable industry. During the Depression no one in insurance lost their job.’

“What we do is 90% common sense and 10% technical capability,” said Dupre.

To emphasize how that common sense is always present, he related a story from early in his career: “I was on a date to one of the trendier spots, and as we walked in, I noticed that there were no sprinklers and only one exit. I said to my date that we had to go. I declined that risk. Now my date declined further dates, because I was too paranoid, but that was part of the risk.” &

Gregory DL Morris is an independent business journalist based in North Carolina with 25 years’ experience in industry, energy, finance and transportation. He 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]