Middle Market Spotlight: Meet Ashley Skopek, VP, Retail Regional Lead

In this issue of our Underwriter Spotlight Series, we’re excited to feature Ashley Skopek, At-Bay’s Chicago-based Vice President, Retail Regional Lead. 

According to Ashley, the biggest factors that drove her to join At-Bay were the InsurSec approach, which helps improve policyholders’ security postures as part of their insurance policy, and the work/life balance that allows her to focus on her growing family. Ashley brings 15+ years of insurance industry experience at AIG and Chubb, where she focused primarily on underwriting cyber and professional lines.

Learn more about Ashley’s background, her recommendations to brokers in the middle market space, and the career advice that has shaped her underwriting approach in this spotlight. 

1. How did you find your way into the insurance industry?

Like most people in the insurance industry, I took a pretty unique path to get here. I majored in Criminal Justice at Illinois State University and aspired to land a federal job in criminal investigations. I interned at the General Services Administration and absolutely loved it, but when I graduated, the government had just gone on a hiring freeze. The special agent in charge at the time suggested I get an MBA or a couple years of relevant experience so I could apply later at a higher level. 

I enrolled in the Loyola Quinlan School of Business for my MBA, and a friend working in personal lines insurance at AIG recommended me for a position in operations. From there, I was promoted into underwriting, and to my surprise, I really enjoyed it. I stuck it out, and three years later, I transferred to the Professional Liability & Cyber team — and the rest is history.

I believe things worked out for the best, because once you’re familiar with my personality and 5’3″ stature, it’s pretty clear that not following my initial career path was probably a blessing in disguise. 

2. Why did you decide to join At-Bay?

All carriers are trying to write business in a world with dozens of markets that have all deemed cyber as a growth product. Before At-Bay, I had spent my entire career at very large and well-established carriers that had built a name and reputation for themselves not just on cyber, but on a wide variety of other products.

While I’m grateful for my time spent at these organizations — which taught me everything I know about cyber — joining At-Bay has allowed me to leverage what I’ve learned while also working for a more agile organization. At At-Bay, I can transact faster while still remaining true to underwriting diligence and committed partnership with our broker and client partners. Plus, as a specialty cyber player, At-Bay has deep domain expertise, cyber-specific risk modeling, and the agility to rapidly adapt to the evolving threat landscape.

I’m first and foremost a mom (of two with another one on the way). I love my job and like to think I’m good at it. But my passion is truly my family. I love it that I work for an organization and people that makes it acceptable to have and be good at both! 

3. What’s something you want brokers to know about At-Bay? 

For starters, At-Bay is a full-stack insurance provider writing on our own E&S carrier’s reputable paper with an in-house Claims team. We leverage both technology and traditional underwriting methods to allow for speed to quote while maintaining underwriting excellence and sustainability.

Importantly, we strive to help make clients better. No matter where we sit in the insurance tower, we offer a broad and competitive suite of security products included with every Cyber and Tech E&O policy. The policy’s Embedded Security fee gives At-Bay insureds access to tabletop exercises and unlimited consulting hours with our expert security Cyber Advisory team, whereas other providers may charge per tabletop exercise or include only the first one to two hours of consulting.  

4. What security controls do you recommend to provide more favorable terms and coverage?

Ransomware and business interruption claims aren’t going anywhere, but systemic risk and data privacy claims also seem to be notable as well; and the claims / litigation environment there is constantly evolving. An evaluation of policies / procedures / controls surrounding these types of exposures are crucial as well.

That said, it’s important to underwrite each risk individually. Multi-factor authentication, Managed Detection and Response, and strong patching cadence are solid starting places — but other controls should be risk — and client-dependent, taking into consideration factors like revenue size, industry class, footprint, and budget. The needs of each client will differ, and At-Bay’s underwriting team can help brokers advise clients on a case-by-case basis while adapting our underwriting criteria in tandem.

5. What’s the best career advice you’ve ever received?

Early on in my career, a senior leader who had previous tenure on the broker side told me to always remember that when you find yourself needing to communicate a challenging message to a broker, always remember that when you communicate the message to them, it’s business… but when that broker has to communicate the message forward to their client, that conversation is personal. So, no matter how hard the message was for you to communicate, it’s likely 10X harder for the broker. 

This insight has stuck with me throughout my career and has shaped my underwriting style. I like to think I communicate challenges with purpose and reason. Only if I myself can understand and explain the reasoning behind a given message can I expect a broker and, by extension, a client to understand. This has made me as transparent as I am today, and it’s the reason “why” has become my most-used word. 

About At-Bay

At-Bay is the InsurSec provider for the digital age. By combining world-class technology with industry-leading insurance, At-Bay was designed from the ground up to empower businesses of every size to meet cyber risk head on. At-Bay Insurance Services, LLC provides insurance protection and security prevention solutions to close to 40,000 businesses in the US, safeguarding up to $800B in collective business revenue, and offers coverage by admitted and non-admitted insurers for Cyber, Technology Errors & Omissions (Tech E&O), and Miscellaneous Professional Liability (MPL). The At-Bay Group also includes an active full-stack insurance company and a cybersecurity company. At-Bay Security offers proprietary cybersecurity solutions including At-Bay Stance Managed Detection & Response (MDR).