As a part of our interview series called “Women Of The C-Suite,” we had the pleasure of interviewing Cheryl Sinclair.
Cheryl Sinclair is Chief People Officer at Buckle, an inclusive tech-enabled financial services company, where she implements HR systems and initiatives to support the company’s growing team to advance the gig economy, while ensuring diversity, equality, and inclusion. Previously, Cheryl spent nearly 20 years in various human resources roles at Farmers Insurance, most recently as Assistant Vice President, Human Resources. While at Farmers Insurance, Cheryl designed a business-based HR model still in place today, leading a team of 50+ regional HR partners across multiple states and lines of business for over 20,000 employees. She was also Head of Talent Management for Holland America Group, serving Princess Cruises, Holland America Line, Seabourn, and P&O Australia. Cheryl specializes in leading diverse teams through organizational change and complex transformations while maintaining a positive and inclusive environment. She has a bachelor’s degree in business administration and management from Texas Tech University.
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 never considered a career in Human Resources. I actually wanted to be a dancer, but my father encouraged me to go to business school. After college, I had a series of work experiences that led me to connect with someone, who ultimately became a good friend and colleague. She helped open doors for me that otherwise may have been challenging to break through on my own. I did the work, and it started me down a path to take on a number of incredible people-related roles over the years. I have learned so much from hundreds of people I have met and supported.
Can you share the most interesting story that happened to you since you began leading your company?
I am the first Head of HR for Buckle, the inclusive digital financial services company serving the rising middle class and providers to the gig economy. Before I joined, I spent quite a bit of time thinking about some of the key strategic initiatives we might need, where I might focus my efforts, and where I can add the most value. Taking time to plan and define your first 90 days is so critical when starting any new role. However, you have to be prepared to be flexible, adjust, and adapt as needed. In my first 90 days, I spent time supporting the business on initiatives that were unexpected, but critical.
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 was very task-oriented early in my career. I wasn’t comfortable with small talk and felt that it was the biggest waste of time. Boy, was I wrong. During one of my first meetings as a new HR leader, I walked into a room, said hello to the people seated at the conference table, and immediately started talking about a project I was leading. Ten minutes into my presentation, my boss stops me and asks me to turn around and read the room. “Read the room? What is she talking about?” It quickly became apparent. Everyone had left. There were some senior people in that room, but my inexperience, lack of care and failure to connect with others, was one of the most embarrassing moments of my career. I laugh about it today, but after all these years, this moment still serves as a strong reminder regarding the value of connection. It doesn’t come naturally for me, so now I am very intentional about taking the time to listen, get to know people, and build meaningful relationships.
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?
I am so fortunate to have worked for and with some incredible women over the years — from my first manager who gave me some tough love, to the person who created pathways, to executive leadership roles as my sponsor behind the scenes. Women supporting women is one of the most powerful things we can do in life — not just in the workplace. We understand each other. We each have a story to tell and incredible gifts to share. I am grateful for every leader who took the time to invest in me, equipping me with the tools to coach and mentor others in their career journey.
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?
A couple of years ago, I started scheduling time on my calendar to workout, read my devotion, and mediate at the start of each day. I felt the need to put more focus on my own mental health and wellbeing, especially during times of uncertainty or when I anticipate high demands of my time during the week. This time of “personal connection” has brought me so much peace and provides an outlet to process and keep my thoughts in balance.
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?
We spent the last year being intentional about building our leadership team, which includes three women and people who have diverse backgrounds and experiences, because the insurance members who Buckle serves are also very diverse. Buckle provides insurance and credit products to gig economy rideshare and delivery drivers who typically earn less than the average American wage and are subsequently penalized for having poor or no credit. Diversity and inclusion is foundational to who we are as a company and how we run our business.
Look at your business, target audience, customers, potential customers, guests, policyholders, employees, and stakeholders. Since these are the diverse people who you serve every day, your executive team must be diverse too. Far too often, we see examples where leaders “seem” to be out of touch or unrelatable. The reality is they may not have a point of view or experiences that allows them to understand the needs of a wide range of diverse people. In today’s times, it should be foundational for all businesses to have diverse executive leadership teams. You have to put in the time and work to do so.
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.
To be inclusive, you have to care about people and operate in a way that involves empowering and equipping others to thrive.
For me, representation is important and shouldn’t be minimized. We want to see ourselves in others. I see comments from time to time where people point out that it shouldn’t matter if the person is the first woman or first black woman, but the reality is, it matters. As a black woman, I still see articles about the many firsts still taking place in so many places. I feel a personal sense of pride in those individuals, and it continues to give me hope in my future and the future of other women and women of color.
Equity is an acknowledgment that some are not afforded the same opportunities to thrive. I have benefitted from doors being opened for me. I did the work, but the path was cleared in situations where I ran into obstacles. This work is intentional and should be done in a way that honors, respects, and meets people where they are.
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?
Being in HR for so many years, I have spoken with a lot of people at all levels of the organization, and a common theme that has come up for me over the years is “visionary.” A visionary leader is typically defined as a person who has a clear idea of how the future should look, and then they lead a team of people in that direction. While you don’t necessarily have to be the CEO to possess visionary leadership, I have found that employees typically see or look to the CEO for this type of leadership. The balance for CEOs and other senior leaders is how to stay aligned with other leaders in the organization who are also tasked to carry out strategic goals of the organization.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
I used to think that a CEO or executive had to have all the answers. As such, I approached my first executive role with that mindset. I spent more of my time trying to have all the answers and be right, that I failed to understand that you get the best from your teams through your ability to lead, encourage, and create an environment where every employee can thrive.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
Relationship building at this level is just as critical as delivering business results. Earlier in my career, I believed that if I just did good work, it would be enough to establish credibility, earn trust, and be included. It has taken more work on my part to connect with my male colleagues and proactively take steps to be included or even be invited to networking opportunities, that some of my male colleagues didn’t experience. Those interactions create opportunities for face time, visibility, negotiating deals, setting up future ventures, etc. We have more work to do to break down those barriers and create cultures where inclusion is the norm and we don’t have to fight for it.
What is the most striking difference between your actual job and how you thought the job would be?
I am an HR executive, so there has always been a balancing act of finding ways to deliver value to the organization at the strategic level. I never realized how much my actual job would pull me into so many different directions, navigating competing priorities, and constantly feeling as if every initiative is a priority. I quickly learned the value of writing things down and have become much more effective at visualizing where I am spending my time and where I am delivering value to close those gaps.
Is everyone 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?
Like others, I was told growing up that you can do or be anything you want if you worked hard and believed in yourself. That is true to some degree. The culmination of our experiences, upbringing, education, drive, motivations, ambitions, etc., takes us each on a journey that is uniquely carved out for each of us. I never saw myself being in an executive role and others close to me would have thought the same. My path to an executive role was based on a lot of encounters with incredible people who saw potential in me that I sometimes didn’t see in myself. I was also surrounded by great mentors, personally and professionally, who helped shape my view of what I could achieve. What helped me was to say “why not” every time I was either asked to take on a new role, relocate for another position, or step in to help in an area where I had little expertise. Leadership is not easy and is not for everyone. Executives must be willing to learn every day, listen and inspire others, be confident and decisive, be empathetic, and exercise care.
What advice would you give to other leaders to help their team to thrive?
Trust your instincts and do what feels right when it comes to supporting your team. Our ability to connect, show empathy, and kindness goes a long way. You don’t need complicated programs and initiatives to inspire people. On a basic level, most people want a sense of belonging or to be seen and heard. When we create an inclusive environment of openness and care, where everyone has an opportunity to contribute, the team will thrive.
How have you used your success to make the world a better place?
I genuinely care about people. I have always been a good listener, have high empathy, and have always had a high calling of service, both in my personal and professional life. Most people I have encountered over the years would say they felt encouraged, supported, seen, understood, or heard. We have so much more in common than we do differences, so I always approach situations to find common ground. That approach doesn’t work for all business decisions or interactions, but it serves as a foundation for who I am as a person and my intentions when interacting with others.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Be flexible … really flexible — I spent a lot of time developing plans for myself and my team, understanding that there are clear deliverables that need to be put in place. Other priorities that I did not anticipate or planned for resulted in re-prioritizing and shifting gears constantly. Being adaptable and flexible is so critical and necessary during times of immense change.
- Be patient with yourself — I am a list maker and having a sense of accomplishment is important. I find there are moments of frustration that make me question my own ability at times, even though I have found incredible success in the past. In those moments, I put my head up and tell myself, “You’ve got this!”
- Be patient with others — As an emerging growth company, there are so many competing priorities. I had to quickly learn and gain an appreciation for the journey the Buckle team has been on to grow our business and support our people.
- You are needed more than you know — As I work with leaders, talk with employees, and see the rapid growth of our company, I did not anticipate how well I would be received and how supportive the leaders I work with would be. It’s very refreshing.
- Be prepared to dust off some old skills — I have been fortunate to lead large teams for most of my career, working with talented people who are great at what they do. Taking on a role with less people and resources forces you to tap into your own skillset and be more hands on. My knowledge and experiences are broad and have served me well, but it’s been fun and quite interesting tapping into skills that have not been used in a while.
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.
Others have said it, but be kind to one another. With tensions high on so many issues that have unfortunately divided us more than united us, we must work hard to look for common ground first and listen and learn for understanding. We all acknowledge that there are tough issues to solve in the world, but we all have the ability to inspire our families, communities, colleagues, and friends, one person at a time.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Maya Angela said, “Each time a woman stands up for herself, she stands up for all women.” That has rung true for me. I have personal and professional examples of times when incredible women “stood up” or “stood in” for me to either remove barriers or help establish a path forward for me.
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.
There are so many to list, but top of mind for me would be the incredible actress and director, Regina King. Her phenomenal body of work was no doubt achieved with all of the things I spoke about today — integrity, kindness, hard work, empathy, perseverance, and a visionary. You can see these characteristics in her work both as an actress and a director. There are several incredible people doing master classes right now. I would be in the front row for hers.
