Heather Wilson of CLARA Analytics: “Prepare for any crisis”

Interactions with stakeholders — (There are a lot of stakeholders to engage and communicate with as a CEO, as well as many who want to speak with me, so prioritizing and shaping those interactions are critical.) Prepare for any crisis (Anything can happen as a CEO so be resilient and create that mindset as a leader and […]

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Interactions with stakeholders — (There are a lot of stakeholders to engage and communicate with as a CEO, as well as many who want to speak with me, so prioritizing and shaping those interactions are critical.)

Prepare for any crisis (Anything can happen as a CEO so be resilient and create that mindset as a leader and lead the team through it.)


As a part of our interview series called “Women Of The C-Suite” , we had the pleasure of interviewing Heather H. Wilson.

Heather H. Wilson is the Chief Executive Officer of CLARA Analytics. She has over a decade of executive experience in data, analytics, and artificial intelligence. Ms. Wilson was named 2015 Insurance Woman of the Year by the Insurance Technology Association.


Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I was a Rotary Scholar in college studying in Japan and Russia. My first entrepreneurial experience was starting an export-import business in Russia as the country was being westernized with several consumer products during my senior year of college in 1993. I was able to buy my first car because of that venture! After university, I “grew up” in consulting the first 15 years of my professional career with Deloitte and Andersen, to name a few, so constantly thinking about client service, problem-solving, and a customer-first mindset is in my blood. My transformative business approach and data analytical curiosity led me to work across several industries over the last 15 years, including healthcare, banking, insurance, and retail. I was the first Enterprise Chief Data Officer of AIG, the first female Enterprise Chief Data Officer of Citigroup, the first EVP Chief Data Scientist of L Brands, and Head of Innovation/Advanced Technology at Kaiser Permanente. I always embraced the changing role in companies and enjoyed building new opportunities. As such, I was always passionate about driving the data/analytics/AI agenda to build products, drive outcomes, solve problems, and deliver results. The fun and challenge of it all have been convincing my colleagues within organizations what is possible with data and analytics. It leads to amazing transformations; doing this created a strong muscle of influence, collaboration, and determination inside of me. The sense of achievement of creating a tangible solution and driving it to commercialization is what I thrive on. It’s the same feeling as when I first learned coding in my early 20’s almost 30 years ago!

When I look back at my past success, it has come from being ahead of my time when inventing or applying a new concept for a business challenge. As a leader, it’s a forward-thinking data approach that has been my mantra and leading my team to believe in themselves, be curious, and ask questions. Presently, I have been CEO of CLARA Analytics for two months, and with my team, we have already created three new products by diving into the data, the data science models, and the engineering. I am a strong advocate for women in the workforce and diversity. I hope the examples I set with my leadership and collaborative approach inspire my team to set high goals and achieve them. I have also enjoyed mentoring many young executives and helping them to achieve their dreams. It’s important to pay it forward.

Can you share the most interesting story that happened to you since you began leading your company?

A few months ago, we faced the problem of convincing a potential customer that we are not here to compete with their internal capabilities but to augment them, this problem was keeping the customer from moving forward with us. At the time the word “opportunity” was not the mindset or used in the statement above but the word problem. I knew that as CEO this word was part of the culture and a mind-set shift was needed throughout the company. I needed to make changes and create new momentum coming out of the first phase of the pandemic, put on new glasses and change the culture. Change starts at the top, I look at every problem as an opportunity: to change course, communicate better, revise, review, edit and invent. I will never let the word ‘problem’ exist anymore in our company culture and my mindset. Problem is a negative word — it doesn’t bring in creativeness or entrepreneurship. I look at every day’s challenge as an opportunity to be better and entrepreneurial as a leader and ask my team to do the same. As a result of that problem in the story above, it became an opportunity — we rebranded ourselves better with our messaging. The opportunity made us dig deeper and become more apprised at CLARA of what our story is and how to refine it. As a result: CLARA is a partner to our clients, and our data products are an enabler for our clients. Clara is the brilliant spark plug making the parts in the data process move faster, streamlining the delivery and wealth of information, and delivering considerable savings to the end-user. This opportunity has led to successful onboarding of new clients.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I can tell you a story about my first entrepreneurial effort in another country that made me run fast! I was invited to attend a university in Moscow, Russia by a former mayor of Moscow in 1993 which was a very tumultuous time for President Yeltsin and the entire country as it was on the brink of westernization. Another student and I saw the country’s transition to capitalism as an opportunity for importing and exporting American consumer products. Of course I was young and ambitious and only saw the venture through a rose-colored set of glasses. However, not everyone in the country was embracing westernization so our venture was met with some resistance when we were physically trying to get products into the stores and kiosks. I remember at one point being chased down a street and just throwing products. I can laugh about it now, almost thirty years later. The experience really taught me a lesson early on in life about product introduction and commercialization. Because I have a strong entrepreneurial and new product development mindset, I always need to ensure I know when to introduce new products/innovation into the marketplace because my thinking is a few years ahead.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

When I was in my mid 30’s and I was working for Kaiser Permanente, I became acutely aware of my being in a very male-dominated field as it pertained to engineering, technology and data sciences. I approached at the time the Chairman and CEO of Kaiser Permanente, George Halvorson, about starting a KP Women in Technology Employee Group that would focus on the mentoring and advocacy of women in science, tech and engineering. Without pause, George said, “We have to do this, and I want to personally kick off the initiative so the employees see my 100% support.” While I was genuinely appreciative of George’s immediate positive reaction, it did make me wonder what from his past experience compelled him as a male leader to be onboard so enthusiastically. He relayed to me that he had seen his own mother struggle as a strong female leader. As the head librarian of a public library, his mother had a vision to move from paper book records to electronic book records. She pitched the idea over and over again to her management and not only did they not support her, but they wanted to remove her from the head librarian position. He witnessed first-hand what so many female executives have faced and has never forgotten what has happened to his mother.

George provided me so many wonderful opportunities when I was at Kaiser Permanente to grow as a leader beyond supporting KP Women in Technology. He believed that I could lead some of the most transformational initiatives at that time at Kaiser and even gave me my first opportunities to present to a Board of Directors for the first time. His sponsorship gave me tremendous confidence in myself to go have impact and make a difference. I will always be grateful and thankful to his mentorship and him truly walking the talk of Diversity and Inclusion almost 20 years ago.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I love collaborating with people who bring the same. I roll up my sleeves and dig in, and I get everyone around me involved in preparing for a big event. Once I’ve tapped those around me for input and ideas, I spend a bit of “alone time” integrating all the input into messages that I feel confident in delivering in my voice. But I don’t do that in a vacuum. I’m always bouncing ideas off people as I hone the message up until the meeting or making the decision. I am one hundred percent engaged in the task at hand when I’m working on it, but I take the time needed to disengage and re-energize myself. I recharge by sitting in my favorite spot with a lovely view and meditating. I like to meditate daily early in the morning and in the evening also, even while flying it’s great, it seems at 20,000 thousand feet up outside of your work bubble floating in the clouds you can get a much better perspective. I have learned that my quiet time — thinking time is critical. I need the thinking recharge time as much as the active time. This recharge time is when my intuitive voice comes in and helps reveal answers, thoughts and strategies to something that needs solving or finalizing. Many times when the plane lands I have made the call that was needed. Or after a brief hiatus, had the right answers to the opportunity presented.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

It’s important to have a diverse executive team because solving a complex problem benefits from a variety of perspectives and thinking. There are many stakeholders impacted by the decisions senior management teams make and unless there’s a diverse group thinking through the problem, a decision is likely to be sub optimized with respect to all stakeholders. So, diversity is important to reach better decisions. You must have a global representation for a successful global point of view.

Diversity in senior leadership is also important so all employees can see some of themselves represented there. Diverse workforces deliver better outcomes at all levels of a company. I want to hire the best and the brightest for every job, regardless of their race, ethnicity, gender, and sexual orientation. To do that it’s important that employees and prospects see that they can achieve whatever they want at CLARA — that there are no ceilings of any type.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

First, I believe it starts with self-awareness. Leaders need to always be aware of their own biases and how they can get in the way of being effective in any situation.

Secondly, being more empathetic is another key step. Taking the time to understand why others have different opinions and letting them know their input is valued goes a long way to bringing people together. Asking a lot of questions to get everyone’s “backstory” is a good way to do this. People like to share their experiences and what they take pride in. When they feel appreciated, they are willing to engage more fully in the task at hand. And they are more willing to set their own biases aside.

Finally, I think leaders need to minimize how many assumptions they make up front. Situations are all different, no matter how much they might seem to mirror something that happened previously. Effective leaders need to balance their desire to charge ahead quickly and taking the time to assemble the relevant facts.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

I think one difference about being a CEO is that you must think through all the potential consequences of a decision. At my level I must consider all the stakeholders in a decision and figure out what’s in the best interest of the company considering all of them. In previous jobs I’ve had to consider a variety of stakeholders in my decisioning, but not as many as I do now. To do this effectively a CEO must integrate all the relevant perspectives and input…and sometimes much of it is contradictory…to arrive at an optimal decision.

Communicating effectively is important for all leaders, but as CEO all eyes are on you…all the time. Being able to explain how decisions are made, and why the outcome is not always the most popular choice, is a talent every effective CEO needs.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

I’m certainly fortunate to have the title and all the benefits it brings, but there’s more to doing the job well than many people think. First, as CEO I truly feel the weight of the company on my shoulders. Not that everything is up to me — I have a great team of employees working with me to assure our success, but at this level I feel fully responsible for what happens. That’s something many people might not appreciate or see. And I have to work extra-hard to not let that added responsibility interfere with the rest of my life, because that’s not fair to my family and friends.

Another “myth” is that as CEO, I have all the information and knowledge at my fingertips. To some degree it’s the opposite of this! It’s human nature for people not to share unflattering or negative news “up the ladder” so to speak. Therefore, I must ask a lot of piercing questions sometimes to get at the complete story. Hopefully, the way I do this is perceived as engaging and not punitive, so people feel more willing to be transparent with me.

Finally, the myth that the CEO is “the boss” is a bit untrue. Yes, in most settings I am the boss, but I also have six bosses whom I work for–each member of the board of directors as well as my shareholders. Sometimes they act as one, but they are all individuals and deserve to be treated by me with equal respect and attention.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

Things are clearly getting better for women executives, but there is still a long way to go. I think it all comes down to one thing: stereotyping. More and more, we are seen as individuals and evaluated on our merits and talents, but so many people — not just men — hold on to beliefs and attitudes that we are inferior in some way and not cut out for senior executive roles. My hope is that progress in getting beyond this issue won’t progress in a linear fashion. As more and more women’s actions and success put a stake in old stereotypes, people’s beliefs that perpetuate them will wither under the burden of the evidence. And those who refuse to change based on the evidence will lose their credibility and eventually die.

What is the most striking difference between your actual job and how you thought the job would be?

That’s hard to say but I can tell you that I am having a great deal of fun! Hollywood likes to portray CEOs as gruff, unfeeling people whose idea of fun is crushing a competitor or cashing in their stock options. For me at least, I truly love engaging with our employees every day. I share my energy and positiveness with them, and I get the same right back. I help them feel good about their work and about themselves. When I see that in their faces, it makes me glow. And that’s what I define fun to be.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

No, I don’t think everyone is cut out to be an executive, just like not everyone is cut out to be a singer, a professional athlete, or a craftsperson. Every profession has its unique set of skills and talents required to be successful. That said, I believe getting to the top of one’s profession, regardless of what it is, requires some of the same traits and behaviors: relentless energy and determination, picking yourself up off the ground when you fail, emotional AND intellectual intelligence, and being able to think several steps ahead. Executives also must energize those around them about a common objective and lead them in pursuit of it. Not everyone is capable of or wants to do that, at least not to the degree needed at this level.

What advice would you give to other women leaders to help their team to thrive?

The best advice I can offer is to be inclusive. Think about the negative behaviors of leaders you’ve experienced in the past and don’t repeat them. Your voice may not have been sought or heard in the past, but now that you are a leader make sure others don’t experience the same thing. Assume everyone has something to contribute and encourage them to put it forth.

Providing opportunities for everyone to grow in some way is key too. I remember and appreciate leaders who did this for me, and I believe it’s my obligation to “pay it forward” by doing the same for others.

Finally, I think it’s important to listen twice as much as I talk. Some leaders tend to dominate dialogue from the outset which stifles others from speaking. Set the stage, get out of the way, and then bring everyone together after others have had a chance to speak.

How have you used your success to make the world a better place?

By being a role model for others. I’m far from perfect but I believe how I conduct myself, what I’ve achieved, and what I stand for helps others figure out the kind of person they want to be. Whether it’s my friends, co-workers, children, or someone I don’t know who reads this article I am purposeful about my actions and behaviors. Hopefully that influences the choices others make in a positive direction.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

  • That there was going to be a COVID Delta Variant, second wave to COVID (We had just returned to the office and four weeks later with the Delta Variant spike, we were back working from home!)
  • Surround yourself with trusted advisors when you become a CEO (It can get lonely at the top so having sound, trusted advisors who have your and your company’s best interests is important)
  • Managing my time and energy is even more important as a CEO (I am the only one who can personally control this so it is even more crucial for a balance life.)
  • Interactions with stakeholders — (There are a lot of stakeholders to engage and communicate with as a CEO, as well as many who want to speak with me, so prioritizing and shaping those interactions are critical.)
  • Prepare for any crisis (Anything can happen as a CEO so be resilient and create that mindset as a leader and lead the team through it)

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

The world faces many tough problems right now. Climate change, hunger and poverty, and seemingly endless wars to name a few. I believe the biggest barrier to addressing big issues like these is perceiving constituents affected by them who aren’t like us as “others” who benefit only if we lose something in the bargain. If people could set aside all their cultural, political, and other biases to work together on solving the world’s problems, humanity would make much more progress faster. I don’t believe people need to give up on who they are, where they come from, what they believe to do this. It’s more about respecting other cultures’ heritages and coming together despite our differences.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I have lived my life with a fire in my belly of passion, kindness in my heart and a mind that always craves to learn more so both as a CEO and a human being the following quotes are ones I live by professionally and personally.

I constantly encourage my team to embrace “lifelong learning” — even Miachaelangelo at 87 years of age said, “I am still learning.” To do this well it requires listening and reading. It is how I have always evolved myself being in the field of analytics, AI, engineering and technology. Many times during meetings I will kick them off articulating to my team that I am the student and my role is to listen and learn from them. Because I am an attentive listener, I am such a curious person. Albert Einstein said, “Curiosity is more important than knowledge” and that is the essence of me as a leader and as a parent. I have always had this insatiable appetite of curiosity which keeps me dynamic and relevant. I raise my twin sons with the same thinking.

I grew up as a child with a blind uncle around me who played a prominent role in my life. His strength, perseverance and ability to thrive served as a big influence and inspiration for how I was going to live my life with purpose and impact. To that end, I love the following Maya Angelou quote because it embodies how I live my life: “My mission in life is not merely to survive, but to thrive; and to do so with some passion, some compassion, some humor, and some style.”

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

MacKenzie Scott. There are so few of us who are female CEOs in the tech and science start-up space. Her philanthropic work focusing on gender equality and heightening the need to offer more women opportunities in technology is what I have been pushing for over a decade as evidenced by my formation of women in tech employee groups. Her work is also trying to elevate the message to empower more women to advance in leadership roles — this is what I have spent my career fighting for inside organizations.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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