I recently went one-on-one with Mary Boyd, CEO of Hiscox USA.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here?
Mary: I’ve been in the insurance industry for 30 years now, starting my career as an actuarial analyst. But I really see myself as a business builder – cultivating teams, relaunching strategy, and developing solutions. Each of my experiences over the years has paved the way to Hiscox USA, where I have the opportunity to propel the business to the next stage while also preserving its core DNA. At Hiscox, egos are left at the door, and it’s a very supportive environment, which is congruent with the way I’ve always worked and how I commit myself to my career.
What I really admire about the company is the customers we serve – the small business community. With 35 million small businesses in the United States, they are responsible for roughly half of our nation’s GDP, so we’re really representing the lifeblood of the country. Hiscox gives small business owners peace of mind, so they can continue to run their businesses, pursue their passions, and not worry that one mistake will cause financial ruin. I’m grateful that I’ve landed in a place where my life’s work enables small business owners to pursue their life’s work as well.
Adam: What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Mary: In the early to mid-part of my career, I was a senior actuarial analyst, and I was pretty good at it! But at the same time, I was also a young mom. My daughter was about a year old, and I struggled to pass the exams at the rate I wanted to while showing up to be the mom and wife I wanted to be. I knew I needed to do something different and was torn between three things: staying in the insurance industry as an underwriter or a product owner, or switching career paths to be an AP statistics teacher in my old high school, where I could take over coaching the women’s tennis team. I ultimately chose the product owner role.
This change accelerated my career as it led me to a position leading operations and then to leading Chubb’s predictive analytics business. Because of my previous exposure to building new products, I was given the opportunity to build an entirely new program there. Eventually, it even steered me towards getting my own patent as the predictive modelling methods and systems we used were my own invention.
This experience completely changed my career trajectory: it positioned me as a leader, forced me to learn different skillsets, and put me under pressure. I learned competencies, discipline, resilience, and how I wanted to be and didn’t want to be as a professional. This was the time of my life when someone said to me, “You are going to be a CEO someday” – something I never truly considered. This made me realize that I was capable. Not only was I ambitious enough, but when things needed to be done, I was ready to stand up and do them.
Adam: In your experience, what are the key steps to growing and scaling your business?
Mary: Study your business and the market to understand the customers’ needs. At Hiscox, we’re proud to be the small business experts; we have a deep understanding of the unique risks small business owners face and are continuously learning and adapting to their ever-shifting external pressures so that we can be a better partner. We’re well on our way to becoming America’s leading insurer for entrepreneurs and the preferred partner to their trusted advisors, and it’s our priority to understand what our customers need and how to build our solutions to help them be successful. When we move along their trajectory, we all grow together. Companies that don’t do that get left behind.
Ultimately, there are several key steps: study your market, study your customer, deepen your relationships with partners, develop solutions together that are collaborative and outward-looking but also reflect inwardly, then develop and execute plans with operational excellence. Finally – and most importantly – make sure it’s the best place to work.
Adam: What do you believe are the defining qualities of an effective leader?
Mary: Achieving greatness requires hard work and a relentless drive to understand three key things: the industry, your team, and last but certainly not least, your own competencies and areas of growth.
We don’t have to be experts in every single field, but it’s important to prioritize continuous learning out of respect for the business, your team, and your own career trajectory.
As leaders, we need to be fully engaged with our teams and bring credibility to every conversation, ensuring that the context we provide is relevant and makes sense. No one wants a boss that comes in and just sits at the top without any integration – a leader needs to be a valuable contributor, rather than just an overseer.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Mary: Always keep these components in mind: set a clear direction, build trust, listen, practice patience, instill confidence in your teammates, and always remember to drive the business forward. Following through is the cornerstone of any strong organization and its leaders.
When people ask me what I do, I tell them I fix, build, and coach. Coaching is the biggest part of what I do because it’s my job to understand the natural talent of the team members and make little tweaks to my own technique to improve individual and team performance. It’s all about identifying a person’s strengths and weaknesses and how they work under stress, so we can pinpoint where they overcompensate and adjust accordingly. We excel when we understand how everyone operates, including ourselves.
I try to be aware of these things in myself and encourage all leaders to have this self-awareness in order to grow. Understanding the whole person is key, which is true on a sports team, in music, and even in an insurance company.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Mary: As a small business insurer, entrepreneurs are the lifeblood of the company. I would first encourage all entrepreneurs to pursue what you are passionate about. Dive deep into your field and learn all that you can in order to deliver the most impactful results. Customers can tell when you love the work you do, so always remember your “why.”
To all those who are looking to make their way as a leader, start to understand your own strengths and weaknesses, and where you fit best in your team. Once you accomplish this, work on recognizing these key qualities in your team members, helping to build confidence and competence. Building trust in your team starts with building trust in yourself.
Of course, as the CEO of an insurance company, my number one piece of advice for all leaders is to make sure your business has the proper protections in place. I am passionate about seeing others succeed, which is why I am a strong advocate for small business owners and leaders to really learn the ins and outs of insurance so they can pursue their passions with peace of mind. Hiscox’s Underinsurance Survey found that 75% of small businesses are underinsured with a large knowledge gap of what policies cover and how often a business should update a policy.
Adam: What is your best advice on building, leading, and managing teams?
Mary: As leaders, a major aspect of the job is identifying and empowering talent. An effective leader brings out the greatness in others, helps to break bad habits, and cultivates skill sets to help the team be better each day. Growth happens when a leader can help their team build confidence in the things they thought they couldn’t do.
Also, always remember that businesses will be most successful when they win together. Teams that play together and for each other win, and the ones that don’t, lose.
Adam: What are your best tips on the topics of sales, marketing, and branding?
Mary: I’m incredibly proud of the superstar team we’ve built at Hiscox USA who are truly gifted in the areas of sales, marketing, and branding. While I may not have had as much experience in these areas, I’ve picked up a few key lessons along my journey. The most important lesson is truly understanding your customer; the problems they are facing and where, how, and when they like to be spoken to. It’s this real empathy with our customer that enables development of products that solves their problem, and messaging that resonates. Without this understanding, you’ll be operating in a vacuum.
I’m also a big believer in helping customers through education. There’s often a knowledge gap about the different and emerging risks that small businesses face, and what different policies do and don’t cover. In fact, the Hiscox Underinsurance Survey found that 83% of small business owners don’t understand what a General Liability policy covers. We help educate small businesses on the new and emerging risks, like ransomware for example, and how to protect their business against them. It’s also our collective responsibility to make insurance more accessible and easier to understand.
Ultimately, small business owners are superheroes; they are brave enough to chase their passion, and to make their dream a reality. Sharing – and protecting – their passion, ambition, and drive is the single greatest thing we can do as an insurance provider.
Adam: What is the single best piece of advice you have ever received?
Mary: Show up. Show up for your family, for your friends, for work, for your team, and for yourself. It doesn’t have to be in any order, but you have to show up.
And, as my grandmother used to tell me, “Sleep, doll!” At some point, you just need to go to sleep!
