I recently went one-on-one with Kevin Kerridge, CEO of Hiscox USA.

Adam: How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?

Kevin: I came from a humble background, where money was tight. My parents may not have had the wherewithal or money to put me through college after high school, but they gave me something invaluable and everlasting: a strong work ethic, respect for others, and doing the right thing. These ideals have always stayed with me, and through my professional journey, I have never forgotten where I came from. In terms of career progression, there are two things I have always tried to stay true to: 1) being part of the solution, not the problem 2) come to work every day with a great attitude and a desire to make a difference. Those two outlooks have served me well.

Adam: In your experience, what are the key steps to growing and scaling your business?

Kevin: I think when a business is young and small, you must have a mindset of scrappiness and of rolling up your sleeves and getting to work. Organised chaos prevails and it is a case of progress not perfection, no matter how inelegant that feels. However, as you get bigger applying that mindset can be corrosive to the business and can create a shaky foundation. At Hiscox we talk about ‘going from a big small business to a small big business’ and the change needed there around more structure, controls, and deliberateness. The transition is key. It is about changing that mindset and culture of scrappiness – putting some structure and process around things – which is never easy! 

Adam: What do you believe are the defining qualities of an effective leader?

Kevin: Someone I have a lot of respect for told me recently that his view of a great leader is that when he or she walks in the room, particularly during a challenging situation, the temperature in the room goes down not up. I subscribe to that and work to do the same. My personal view is that vulnerability is more important than any other quality – or more specifically being comfortable with being vulnerable – saying when you don’t know the answer, asking for help, being human – one of our core values, and showing empathy.

Adam: How can leaders and aspiring leaders take their leadership skills to the next level?

Kevin: This might sound cliché, but being true to yourself and your unique strengths should come above all else. Find what makes you great, and focus on that as your superpower as a leader. Don’t obsess about your weaknesses – they just need to be ‘good enough’. And most importantly, always be authentic. Do not try and replicate something you saw in a leader you loved working for if it is not the authentic you; if you do not believe it, others will not either. For example, I have worked for some great extroverted leaders in the past – but I’m an introvert – so I’ve leaned into the things that make me great as a leader that comes naturally to me, such as being thoughtful, providing calmness in a crisis, etc. 

Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?

Kevin: That’s a big question. First, I love to see people willing and able to disagree more. I encourage people to respect that others have opinions different to yours – accept that that is OK and embrace the power of considering and understanding the views of others even if you don’t share them. “Groupthink” or a group conforming to one opinion and unwilling to dissent, can be the downfall of many. There is no downside to challenging ideas and learning different perspectives; when properly channeled, collective brainpower and diversity of thought can make us all stronger.

Second, every successful business starts with the right talent. Surround yourself with people better than you. Be purposeful in putting the right people in the role.

Third, keep your ego in check. Prioritize others before yourself.  I always work on the principle of business first, team second, me last. 

Adam: What is your best advice on building, leading, and managing teams?

Kevin: Read ‘5 Dysfunctions of a Team’ – it’s an easy read, more fable than textbook, and it has been my leadership bible for over 15 years. From this text, I have learned that if you can push your team through that journey, which takes time, the dividends will be huge. 

Adam: What are your best tips on the topics of sales, marketing, and branding?

Kevin: I am not a marketing professional but here are some broad thoughts. 

1. I always frame marketing as simply selling more stuff, to more people, more of the time. Of course, to achieve that, the product must be right for your intended audience, and sold to them at the right time.

2. Branding is a key element of what we do at Hiscox. Awareness of and affinity with the brand have key long-term benefits – and creates a halo effect for all other in-year activities to get customers to consider your product or service. 

3. At Hiscox, we have always also believed in word-of-mouth as the most powerful form of marketing. 

4. Acquisition of customers is a critical strategic battleground - so we make sure we invest appropriately in order to have the right tools and talent in place. 

5. Finally, marketing is too important to be left to the marketing department. The customer is at the heart of everything we do, and every function has a role to play, even if they don’t directly interact with customers. 

Adam: What is the single best piece of advice you have ever received?

Kevin: In one of the first meetings I ever had with Robert Hiscox he told me that he would forgive me for (occasionally) losing him money but would never forgive me if I lost him his reputation. That always stuck with me, and over the years it became clear that it can take years to build a good reputation and seconds to lose it. Wise words indeed. 


Adam Mendler is an entrepreneur, writer, speaker, educator, and nationally-recognized authority on leadership. Adam is the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal-winning athletes, political and military leaders - for intimate half-hour conversations each week. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities, and non-profit organizations. Adam has written extensively on leadership and related topics, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. Adam teaches graduate-level courses on leadership at UCLA and is an advisor to numerous companies and leaders. A Los Angeles native, Adam is a lifelong Angels fan and an avid backgammon player.

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