Underwriter Spotlight: Meet Brian Maloney, Senior Underwriter

In this edition of our Underwriter Spotlight Series, we’re thrilled to introduce Brian Maloney, Senior Underwriter at At-Bay.* With over a decade of experience in cybersecurity, Brian brings a unique blend of technical expertise and underwriting insight to his role.

Prior to joining At-Bay, Brian worked for a large carrier, honing his skills in underwriting complex technology and cyber policies. His broad industry knowledge and understanding of cyber threats allow him to offer invaluable support to brokers navigating today’s evolving risk landscape. Brian’s commitment to proactive risk management and tailored solutions ensures brokers receive the guidance and confidence they need to meet their clients’ cyber insurance needs.

1. How did you get your start in insurance?

My career began as a special needs teacher where I spent five years mastering the art of relationship-building—mainly by working with concerned parents. This taught me how to gauge temperament, assess needs, and plan for all kinds of situations. During my summers off, I helped a friend sell Cisco products on eBay, which piqued my interest in network hardware. This eventually led to a decade in cybersecurity sales, where I worked closely with engineering teams.

While pitching a cybersecurity product to AIG, I was invited to join their underwriting team to help bridge the gap between cybersecurity technology and insurance. That was my entry into the field, and I’ve since combined my technical expertise with relationship management skills to assess risks and build strong partnerships.

2. How does At-Bay’s technology enhance the underwriting process, particularly in the middle market segment, and how does it benefit brokers?

At-Bay’s technology is a game-changer, especially in the middle market. Unlike traditional carriers and providers, where underwriters often rely on cumbersome Microsoft Word documents and disjointed systems, we’ve built a streamlined platform that consolidates all the information we need into a single repository. This eliminates inefficiencies and errors that can come from juggling multiple data sources and helps us turn around quotes much more quickly.

What makes this even more impactful is that our technology doesn’t take the art out of underwriting—it enhances it. By automating repetitive tasks, we free up time to focus on thoughtful risk evaluation and finding creative ways to say “yes”.

During busy times like the upcoming 1/1 renewal season, our technology allows underwriters to focus on what matters most—open communication with brokers. Instead of getting bogged down by administrative tasks, our underwriters can prioritize getting on the phone, answering questions, and navigating complicated submissions to ensure that even the most challenging risks are handled efficiently.

Ultimately, our top priority is ensuring brokers feel supported, whether they need a quick turnaround or expert guidance on more nuanced risks. This balance of efficiency and expertise allows us to provide faster responses, smoother workflows, and, in the end, better outcomes for brokers and their clients.

3. What specific challenges do you encounter when assessing middle market risks, particularly those with unique cyber exposures, and how do you address them?

Middle market risks often come with limited information in submissions, making it challenging to fully assess exposures. To bridge this gap, we use our proprietary security scan during quote to gain a clearer picture of the applicant’s risk. This allows us to offer tailored coverage solutions, even when the initial submission is limited. We also provide applicants with a detailed security report that highlights their current cyber posture and actionable steps for improvement. This equips insureds with tools to enhance their defenses before a policy is even bound, delivering added value to both brokers and their clients.

For unique cyber exposures in the middle market, we prioritize understanding each business’s controls and aligning coverage with their specific revenue and risk profile. We see this as an opportunity to provide more than just a policy. We want to partner with policyholders to ensure they’re in the best position to manage their risk long-term.

4. Can you share an example of a complex risk you’ve successfully underwritten for middle market clients this year?

We recently underwrote a complex middle market risk for a company providing AI-powered solutions to businesses. As a larger risk with diverse operations, this deal required extensive collaboration. I involved our Chief Underwriting Officer, Michael Drummond, to thoroughly evaluate the exposure. We worked closely with the broker to address key concerns and craft a tailored solution.

Through consistent communication and a team effort, we got comfortable with the exposure and secured a policy that met the insured’s needs. This is a great example of how we partner with brokers to tackle complex risks and deliver results.

5. How does At-Bay maintain underwriting discipline while also being competitive in the current market?

We balance competitive pricing with disciplined underwriting by staying flexible and creative in our approach. For instance, we recently considered a healthcare risk that initially fell outside of our appetite. Rather than declining the submission outright, I recognized that upcoming changes to our guidelines would allow us to consider the risk. I maintained close communication with the broker, and we were able to offer terms after just a few days. Together, we aligned on a competitive price that met market expectations while ensuring the insured’s coverage needs were fully addressed.

This example highlights our adaptability and dedication to supporting brokers. By combining a deep understanding of the market, open communication, and a collaborative mindset, we’re able to deliver tailored solutions and real value to insureds.

6. As the needs of middle market clients grow more complex, what opportunities do you see for brokers to collaborate with At-Bay in addressing these evolving cyber risks?

The evolving landscape of cyber risks, particularly with advancements like AI, demands a proactive and collaborative approach. Risks such as ransomware are becoming more accessible, requiring brokers and insurers to stay ahead of these trends together. At At-Bay, we empower brokers with data-driven insights through our InsurSec reports and ongoing education, helping them guide insureds in understanding and mitigating emerging threats. Open communication with brokers is critical, and by regularly sharing insights about the risks they’re seeing—even those we might not write today—we can refine our appetite and underwriting processes, ultimately improving how we address tougher classes of business.

We also see tremendous value in joint account reviews, where brokers share upcoming submissions or even accounts we’ve previously declined. This transparency helps us identify opportunities to reassess risks as controls strengthen or circumstances evolve. For example, a client with a past claim often becomes a stronger risk after implementing lessons learned.

Collaboration like this not only enables us to adapt our appetite but also helps brokers understand our cadence, policy wording, and approach. Together, we can offer better solutions that address the complex needs of middle market clients and provide greater value in a rapidly changing risk environment.

7. What do you find most rewarding about underwriting, and how does that influence your approach to partnering with insureds to find solutions and improve their risk posture?

What I love most about underwriting is the constant challenge of balancing the needs of the insured and the realities of the risk. Every day is different, and you never know what kind of risk will come across your desk. It’s incredibly satisfying to find solutions and help insureds understand where they need to be in terms of their risk profile.

At the heart of it, underwriting is about partnership. We’re not just issuing policies; we’re working alongside insureds to make them stronger, more resilient. Even the most secure companies can be exposed to threats, so it’s important to recognize that we’re all in this together. Our goal is to support them before, during, and after an incident. We’re here to help them navigate the complexities of cyber risk, and this partnership is what keeps me passionate about underwriting.

The idea that we’re actively helping businesses build better security and recover stronger is something I find really rewarding. It’s a dynamic, ever-evolving space where we can truly make a difference for insureds, and that’s what drives me.

* At-Bay Insurance Services LLC is a wholly owned subsidiary of At-Bay, Inc.

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).