Behind every successful small business lies a story of courage, the courage to invest in an idea, take calculated risks, and keep moving forward despite uncertainty. Yet, for growing businesses, navigating challenges such as cyber threats, liability risks, and financial exposure can feel overwhelming. What these businesses need today is more than just insurance; they need a trusted partner that truly understands their journey, protects their ambitions, and gives them the confidence to grow without fear. This understanding has firmly positioned Hiscox as one of America’s most reputed and trusted names in the insurance industry.

Hiscox is a global specialist insurer with roots dating back to 1901. Hiscox USA is an important part of the international Hiscox Group, which employs over 3,000 people across 13 countries and has customers worldwide.

In the US, Hiscox tailors its diverse portfolio to protect over 600,000 small businesses from risks that may threaten their livelihood. Whether safeguarding digital infrastructure against cyber breaches, providing general liability and professional liability coverage, or delivering specialized entertainment and media solutions, the firm provides protection.

Driven by values centered on people, courage, ownership and integrity, Hiscox does more than just issue policies; it fosters an inclusive, ethical ecosystem where brokers and business owners alike can succeed. Hiscox serves as a trusted partner, empowering modern entrepreneurs to focus entirely on what they do best: building the future of their business and the communities they grow across America.

CIO Bulletin recently had the distinct honor of interviewing Mary Boyd, CEO of Hiscox USA. She shared powerful insights into how Hiscox stands beside businesses as a trusted partner, safeguarding not just operations and assets, but the very ambition and determination that drive them forward.

Interview Highlights

Hiscox has been supporting courageous businesses since 1901. Can you take us back to the company’s inception and share the founding vision that continues to shape Hiscox today?

Hiscox is a global specialist insurer, headquartered in Bermuda and listed on the London Stock Exchange. Our values define our business, with a focus on people, courage, ownership, and integrity. We pride ourselves on being true to our word and our award-winning claims service is testament to that.

We first entered the US market in 2006, and in 2010 became the first US insurer to offer small business insurance online and over the phone in real-time. For two decades, we’ve helped America’s entrepreneurs turn their dreams into reality, protecting what they’ve built and giving them the confidence to thrive and grow. As the small business experts, Hiscox empowers business owners to pursue their dreams.

What range of products and services does Hiscox offer to small businesses, and what unique features set them apart in a competitive insurance landscape?

Hiscox understands that no two businesses are alike. That’s why we provide fast, affordable, and tailored insurance solutions for America’s entrepreneurs, protecting hundreds of professions, including technology-focused enterprises, IT consultants, architects and engineers, web-design agencies, and more. Our offerings — general liability, professional liability, business owner policies, and cyber security coverage, are designed to address the unique risks of each individual business.

How does Hiscox’s philosophy manifest itself in daily operations and customer interactions?

At Hiscox, we’re there for our customers on their best days and on their hardest ones. When a business dream is suddenly at risk, we live our “human” value by showing up quickly, listening first, and doing what it takes to help owners get back on their feet as fast as possible.

That commitment is especially important in moments of crisis – professional or environmental. For instance, wildfires can upend communities in hours, leaving owners juggling personal loss while trying to keep employees paid and customers served. During the catastrophic Los Angeles wildfires in January 2025, more than 16,000 structures were destroyed across 59 square miles. Our team moved immediately to support impacted customers across Southern California.

Rather than risking any wait time during a period of surging claims demand, we advanced one month of business income, giving owners immediate cash flow to keep payroll going, secure temporary space, replace essential inventory, and reopen in days and weeks instead of months. Customers told us that speed and trust made a tangible difference in the middle of uncertainty: for some, it meant staying open rather than closing their doors.

What strategies have driven Hiscox's growth as America's leading small business insurer?

Hiscox’s growth as one of America’s leading insurers for entrepreneurs is driven by keeping the customer truly at the heart of the business; customer needs and feedback shape our strategy and decisions, as well as propelling innovation.

Even choosing where to buy insurance comes down to personal customer preference. Some customers already know what they need and want to purchase quickly online without a conversation, while others prefer to talk it through in person with a local, trusted agent. At Hiscox, we meet customers where they are and how they prefer to transact, whether it’s online, over the phone, or in person through an agent or broker, making it simple, fast, and flexible to get the right protection, without creating unnecessary steps for the customer.

Hiscox has a real-time customer feedback engine to continuously improve the customer experience, using structured customer insight to drive product innovation and design, and guide business decisions.

Customer trust is critical in insurance. How does Hiscox balance speed, affordability, and personalization while maintaining reliability and ethical standards?

Trust and understanding are deeply intertwined; when people feel seen, heard, and understood, trust grows. At Hiscox, we build that trust by listening to customers in real time and using feedback to continuously improve the experience, while also helping entrepreneurs make sense of the risks they face and the coverage options available to them.

We also invest in education that removes the mystery from insurance. By addressing common knowledge gaps (for example, through our Business Insurance 101), we help owners understand key terms, what’s covered, what isn’t, and how to right-size protection as their business grows.

Finally, we maintain trust by pairing that transparency with strong underwriting discipline and rigorous ethical standards, and by “being there” when it matters most.

Technology and cyber threats are redefining the risk landscape. How is Hiscox helping small businesses prepare for and navigate these emerging challenges?

Education is key, and Hiscox makes significant investments to help small businesses understand new and developing risks, so they can better defend against them and protect their business.

The 2025 Hiscox Underinsurance in Small Business Report, highlights just how important the need for education is: 75% of US small businesses have a heightened exposure to cyber risk, such as by having a website or taking online payments, but 39% thought they did not need insurance because their systems are secure, and 30% because they were too small to be attacked.

The Hiscox Cyber Readiness Report 2026 underscores why defense against cyber risks is so critical: it found that more than half (56%) of US small businesses have experienced at least one cyber-attack in the past 12 months. The report also highlights how businesses can reduce the likelihood of an attack and what to do when one happens.

Looking ahead, what are the key priorities and innovations on the horizon for Hiscox in the coming years? Are there any exciting new products, services, or expansions in the pipeline that clients and partners should anticipate in 2026?

The future is all about making our customer experiences even better. Strategic drivers help us improve processes and cross-business functionality to deliver a better Hiscox experience for our people, customers, brokers, and partners.

A key priority is to continue to educate entrepreneurs about the risks they face, and how to protect their businesses against them. The 2025 Hiscox Underinsurance in Small Business Report found that 77% of small businesses in the US are underinsured, leaving owners exposed to potentially business-ending risks.

The Visionary Leader Upfront

Mary Boyd, CEO of Hiscox USA, has more than 30 years of experience leading businesses and people through transformative periods that span invention, renovation, integration and rebuilding. Known for translating strategic vision into measurable results, she has led large-scale operational, technological, and team transformations that drive innovation and performance.

Drawing on that experience, and with Hiscox serving as a leading insurer of entrepreneurs in the U.S. and a preferred partner to their advisors, Mary is especially passionate about helping small business owners fulfill their dreams with the peace of mind that comes from having the right protection in place. When small businesses thrive, communities and the broader economy thrive too: more than 36 million small businesses contribute roughly 43% of U.S. GDP.

Mary leads the Hiscox team in delivering solutions that help business owners manage risk through education, risk mitigation, and access to a growing network of professional services, backed by an A+ AM Best-rated carrier, so entrepreneurs can grow with confidence.

“At Hiscox, we’re there for our customers on their best days and on their hardest ones. When a business dream is suddenly at risk, we live our ‘human’ value by showing up quickly, listening first, and doing what it takes to help owners get back on their feet as fast as possible.”