Kimberly Simon of Control Case: “When people feel uneasy around you, it’s the perfect time to let your hair down”

When people feel uneasy around you, it’s the perfect time to let your hair down. It means you really don’t have to be in fighting mode, this is where you show your vulnerable side and connect with people on a human level. You stay true to who you are and empathize that someone is feeling […]

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When people feel uneasy around you, it’s the perfect time to let your hair down. It means you really don’t have to be in fighting mode, this is where you show your vulnerable side and connect with people on a human level. You stay true to who you are and empathize that someone is feeling uncomfortable, and you connect. This is when we’ve seen Michelle Obama dancing around the stage and smiling from ear-to-ear. When people are uneasy around you, take interest in them and listen to connect.


How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series I had the distinct pleasure of interviewing Kimberly Simon.

Kimberly Simon manages Marketing and Strategic Partnerships at ControlCase — a global multi-million-dollar cybersecurity certification and compliance company. As a leader, Kimberly brings a certain level of energy and confidence to the table, those attributes draw people in and help her build relationships naturally and authentically. Kimberly is passionate about smart technology and how technology can be used to improve how we live and manage business. She has been featured on Global News, The Good Morning Show, Hospitality Magazine, Thrive Global and Media Lab.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

I was born in Harare, Zimbabwe. My grandmother had 10 children — she sold vegetables at the market to partner with her husband to support the family. So even way back then in Southern Africa, women have always worked in the industries that would take them. Fast forward to the 80s when l was born (because a lady never tells her age lol), my mother and her 5 sisters were fierce. Non of the women l was surrounded by were timid, these women were hardworking career women and hustlers who always went after what they wanted. Some were married and some were not, some had jobs, some ran their own businesses. So, l always knew that journeys were different, and we each have a responsibility to do our best with what we have. I also learnt that success takes many different forms of happiness, and it is not anyone’s place to judge a journey they have never walked.

Life happened and l lost my father and later my beautiful mother and 2 of her sisters. That kind of loss at a young age is devastating. I learnt the lessons of grief, pain, and uncertainty very early in life. As an adult l have the rare ability to digest challenges and bad news in a constructive way. I feel pain and anger just like others; but l take the lesson and keep moving.

Oh l digressed… back to the story, l was then blessed to move to England and stay with one of the 3 remaining of my mother’s sisters for my secondary education. l went to Pimlico School in London for high school then off to University of West London and University of Liverpool for my Bachelor’s and Masters degrees. I have travelled the world and met so many different people but those values of strength, resilience, family, and sisterhood that my mother and her sisters instilled in us are at the foundation of me. It really does take a village.

Can you tell us the story about what led you to this particular career path?

Sure — l am a firm believer that if you try your best and treat people with care and respect, you will end up exactly where you need to be. I never thought l would be excelling in cybersecurity. Fresh out of university, l was working as a Personal Assistant to the CEO of a company called Cohezia in the UK. This was my first office job and wow did l learn a lot. I was fortunate to be reporting to someone who was just a great human — Chandresh Pala. He is patient and super smart. He taught me about the importance of setting SMART goals and being organized in business. This is also where l learnt the art of building meaningful relationships with clients and other stakeholders. Charged with all those lessons and my degree, l was ready for the world. I moved on to work for a marketing company that was instrumental to where life took me. I was given “ControlCase” as my account to manage. One of my deliverables was to organize the ControlCase IT Security conference in the UAE. I remember how excited l was, my first business trip was to Dubai and boy, was that conference a success. I connected with the team at ControlCase and worked hard to make sure they were happy, and l was memorable. I never suspected we’d meet again.

Life happened, l decided to move from the UK to live and work in Dubai for 2 years, then l was off to Washington DC for 6 months before moving back to London. It had been over 3 years since that first conference for ControlCase in Dubai and l was browsing through LinkedIn for any contacts l had in Washington DC; then it happened — Kishor Vaswani, CEO of ControlCase popped up. I remembered him immediately and l was confident that my work with their account had left a great impression. I reached out straight away and asked if there were any marketing opportunities at ControlCase. Remember, if you don’t ask you don’t get. He responded after a few days and said they were looking for someone to manage marketing and events. As luck would have it, he was going to be in the UK on a layover to the USA a week later so we could meet at the ControlCase Europe headquarters and have a discussion. Think about it, what were the chances? Everything just flows smoothly when you’re on the right path.

And that’s how l got into Cybersecurity — l had worked in marketing roles for different industries, but this is where it really stuck. I started working with ControlCase over 8 years ago, the company had less than 50 employees when l joined — today ControlCase is the global leader for certification, cybersecurity and continuous compliance services with over 300 experts across the globe. As the company grew, l also grew within myself and my career. I learnt everything l know about cybersecurity, B2B marketing, sales and relationship management. And personally, l became more confident and seasoned. I transformed my image from that young graduate to a beautiful professional woman who can walk into any room and command it. I can easily take the stage and speak passionately about the company, myself, and my goals. All that took practice and the patience of yet another great CEO, Kishor Vaswani. I still remember that interview l had when he was just in London for a day. He took a chance on me and saw potential that even l didn’t recognize at the time. No matter where life takes me, l will be forever grateful to Kishor and my family at ControlCase for all we have achieved together. It really is the best place to work.

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

As women, we often underestimate our own capabilities and l know society plays a huge part in that. I had been working at ControlCase for about 2 years and thriving on the marketing side. Kishor recognized very early that l have a great ability to build relationships very easily. I like people and good people tend to like me back. I was able to make some powerful connections that resulted in partnerships and large sales for the business. I remember Kishor saying, “do you know you’re a salesperson?”, and l said “no way, l don’t know how to sell anything, l’m just good at marketing.” So he gave me a challenge, l was to learn all l could about our Data Discovery product, a very smart technology that allows companies to scan their entire networks and identify any sensitive data that needs to be protected or removed. I wasn’t even techy like that, but he said, “learn the product and as you talk to people, try and pitch it, if you get a sale, I’ll pay you a commission.” I thought why not! It wasn’t easy but let me tell you, getting my first sale changed everything. I became more confident speaking with customers and a super motivated to learn everything else we sell. I became better on the marketing side because l actually understood the challenges that salespeople face. Today, in addition to my marketing role, l am one of the top salespeople for ControlCase North America. My amazing boss Kishor allows me to work two roles because l love them both and l enjoy the variety. Its hard work, but ControlCase has always felt like a family to me. We support each other to excel.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Reliability — People love someone who is reliable because most people are not. If l say l am going to do something l get it done and if l commit to doing something, you know l’m going to try my very best. To me reliability includes integrity, empathy, and likeability. It is vital to treat people with kindness and respect. Going back to my earlier example. I managed an account well and connected with the ControlCase team when l was just a consultant. I then reached out to the CEO 3 years later. He remembered me as being hardworking, kind, and charismatic so he took a chance on me and gave me the job that changed my life. You never know where life will take you, so you have to be reliable, empathetic, and likeable just incase you circle back to the same people in the future; not to mention, it feels amazing and empowering to come through for someone. Let me add; to me, reliability also means being able to respect myself and meet the promises and goals l set for myself. I can tell you now, I respect myself enough to leave a table were kindness and respect is no longer being served.
  2. Resilience — Whenever things are not going my way; l remind myself that “if it was easy, everyone would do it.” I have so many examples of this because believe it or not, things don’t always go my way. The problem is people see the end result and just assume it was a walk in the park to get here. When l decided to move to Dubai from London, l struggled to find a job. I wasn’t willing to move without securing a position. I tried everything; l was even willing to take a pay cut just to secure a position before l move. I also tried paying a recruitment firm to help with my search, that was just a waste of money. I knew that one of my strengths is that l am likeable and connect with people very easily so if l could just have an in-person interview l was likely to secure something. I decided to use all my savings and take a week vacation to Dubai over the Christmas holidays to look for a job on the ground. I called companies and set up interviews before l landed. I wanted this so much l was willing to walk the street and knock-on doors to find something. I reached out to every contact l had from my first trip to Dubai asking if they knew of any opportunities. The week was a great success, l got two job offers and that’s how l ended up moving. Even the move was difficult, l had used up my savings. I made that move with only GBP200 and lived on a budget until my first pay day. It was difficult, but l knew what l wanted and l was going to have it my way. My spirit just doesn’t let me give up.
  3. Adaptability — I am a champion for change. I realize that change brings with it lessons and opportunities that you would never see unless you take a chance and walk the path. Just over a year into my employment with ControlCase Europe, the company was expanding. They were opening a new office in Ontario, Canada. I had never been to Ontario before; l just knew it was cold out there lol. I remember sitting down for lunch with Kishor (my amazing boss) after the Annual ControlCase Conference in Thailand. It was a beautiful sunny day in Phuket and l was enjoying my coconut drink when he said, “l think we need you in Canada.” He explained that the company was opening a new office in Canada, and he believed l could contribute to the marketing and sales in the region. I was always open to moving back to the USA, but l had never considered Canada. This was a great opportunity to learn and be part of something new. I was sad to leave my family again, but l was also excited for the experience. I took the leap and went with it and wow; l learnt a lot about the steps involved in opening up a business and succeeding in a new market. I also learnt about my own resilience and strength of character. Be open to listening and learning from other people (you never know what they will suggest) and more importantly challenge yourself to getting out of your comfort zone often, this builds character.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

Great question — Let me start by saying powerful women have always been there. Look at pharaoh’s daughter who made the decision that Moses should live. Or my grandmother who sat in the scorching sun all day selling vegetables to support her family. Or better yet, the many female leaders today who are thriving because they lead with empathy and passion. Women are a source of life; whatever you give them they can create with. I think society feels uncomfortable with powerful women because they fear them. A strong woman is proof that women can do anything that a man can do but men cannot do everything that women can do. That’s a lot of power. I can see how that would make some people feel uncomfortable — its theory brought to life.

I also think that society feels uncomfortable with powerful women because they have not normalized us. A strong man is normalized, it is expected by society. The idea of a strong woman has not been normalized — society has not helped us break that glass ceiling.

Without saying any names, can you share a story from your own experience that illustrates this idea?

I work in cybersecurity, so l have many great examples of this. The IT security industry is heavily male dominated, and it was worse so 8 years ago when l joined the company. I represent ControlCase at many industry events around the globe, so l have experienced a lot firsthand. I must say though that how women are treated can be different across cultures or countries. There were certain places l would go and feel that people were uncomfortable dealing with a black woman. Very often, l was one of a handful of women or the only black woman in a room full of hundreds. I have a few pictures from my business travels where l am literally the only female on stage, let alone black female. I remember one event in particular — we had been a big sponsor for that event. I was standing in all my glory at the ControlCase branded booth. A gentleman walked up to me and asked if there was someone from ControlCase he could speak to about his company’s compliance requirements. I told him, l represent the company and l should be able to answer whatever questions he had. I remember how amazed he was that l actually knew what l was talking about. He stayed and spoke with me until he was confident that ControlCase could assist with their needs. I work hard not to allow other people’s misconceptions to change my attitude, so l was true to who l am. I was confident, polite, and light-hearted. I eventually got a smile out of him — l do that. Anyway, before he left the booth, he said it was great speaking with me and he was impressed that a young woman knew what l knew. He confessed that he had assumed l had been hired from a staffing service that provides pretty girls to stand at company booths — as if that’s the only way a woman would be at a cybersecurity event.

What should a powerful woman do in a context where she feels that people are uneasy around her?

Another great question. When people feel uneasy around you, it’s the perfect time to let your hair down. It means you really don’t have to be in fighting mode, this is where you show your vulnerable side and connect with people on a human level. You stay true to who you are and empathize that someone is feeling uncomfortable, and you connect. This is when we’ve seen Michelle Obama dancing around the stage and smiling from ear-to-ear. When people are uneasy around you, take interest in them and listen to connect.

We just need to be better humans and empathize more. You know; life is simple, but we complicate it by assuming roles that are stipulated by the “corporate” world. You don’t have to be a certain way. Its ok to be vulnerable and its ok to empower other people. If you are hard nosed all the time, you miss out on laughing and connecting with others. You miss out on the things that make life enjoyable and complete.

What do we need to do as a society to change the unease around powerful women?

I think society needs to stop looking at the wounded and look at the perpetrators. Society thinks that starting up funds and programs aimed at empowering women is the only answer. You can have all the women’s programs in the world but if we don’t address the perpetrators, we’re not doing enough. We must focus on changing the mind frame of men. Let’s look at WHY there is a boy’s club that gets all the opportunities and WHY men get together at sports and discuss promotions there. WHY they overlook qualified women for positions because they believe a man would do better. Once we understand the limitations in their thinking, as a society we can then create criteria and law around what should be done to support women. Let’s hold leaders and companies accountable for the glass ceilings they have created for women. Let’s scrutinize that behavior and make it undesirable to hold back opportunities from women. Women don’t need help with power, we’re already powerful — we need help changing the perceptions of those that believe we are less than capable.

I also think we need to normalize powerful women. We can do that by exposing society to more women in power. The more they see us and relate to us then the more they become at ease to the idea of powerful women.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

Oh this happens all the time. While on a business trip in Europe, a few companies had been pitching for business with a large firm at a conference. Naturally, the decision maker was a man. He was really enjoying the dances we were all doing to get his business. He decided that he would get a group together and go golfing on Saturday morning and invite people to pitch there. What? I didn’t golf at the time. I just wanted a chance to understand their challenges and see if we would be a good fit — and l wanted to do that during working hours. I didn’t golf, so l didn’t go. I requested we set up some time to talk business the following week and he said he believes he got all the info he needed at golf. In any case, he refused a meeting during business hours, so l offered to take him for dinner and drinks to discuss. That he agreed to. Wow, really. The entire situation was ridiculous and uncomfortable for me but like many women, we endure. I took my boss with me for that dinner, it took a year, but we got the business. I will add, l decided to try golfing (you can’t beat em, join em lol). I actually enjoy golfing now but its ridiculous that l felt l needed to learn just so that l don’t miss some opportunities.

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

Women leaders are often ignored and disregarded in the workplace. There are many cases where men speak over us in meetings. Women also suffer different types of abuse — remember abuse is not always sexual, in most cases its emotional. It’s very easy for people to feed into our imposter syndrome and make us feel like we are not capable, and we don’t belong. So our main challenge is that we are constantly working on our confidence and fighting to be heard. And yet, l have been in rooms where a man puts his hand up to say something obvious and everyone gives him the chance to be heard. The worst is when a woman says something and no one hears it, then a man says the same thing and it becomes a “great idea.” The sad thing is, sometimes people don’t even notice this is happening.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

It is very challenging to be a career woman, especially in the fast-paced industry of IT Security. Things change and move so quickly and if you’re unavailable you miss the discussions, and everything moves on without you. Dating was a nightmare for me because I travel a lot. I never realized how insecure men can be until l was in this job. I remember one relationship ended because the guy l was dating asked me to provide my entire itinerary while l was away and insisted, he wanted to call the hotel phone at night just to make sure l was in my room. I have walked away from many relationships that did not fit with what l wanted to do in my career.

On the family side, that suffered a lot too. I relocated to different countries a few times to progress my career. This means that l missed a lot of family events and celebrations. When there is a tragedy in the family, l am often in a different city away from everyone else, so l suffer emotionally without the comfort of my family.

I struggled to maintain both romantic and platonic relationships because l felt l had to do more if l wanted to succeed professionally. It often felt like while things were going great with the career, when l was home l was lonely. Everything and everyone just moved on without me while l was working.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

For me, a few things happened, l realized that when l am not working l am lonely and unhappy. I had neglected a lot of connections with people outside of work and that needed to change. l also got to a point where l felt more confident within my job and my knowledge. I had given myself time to learn so l could achieve goals faster than when l started, which of course freed up some time. Finally, l grew emotionally so l learnt how to balance my personal life with my career. I really did that by being deliberate and intentional about allocating time to connect with family and friends. l make time to check in on family and talk to them. Another thing that helped is that l intentionally include my loved ones into my life more than l used to — so whenever l am working on something or excited about something — such as this interview- l share it with my family and friends and we create time to celebrate together. Finally, it also helps to find people who understand you. My community knows that l am a go-getter and l have to achieve, so they support that. On the relationship front, l realized that l can only date men who are just as ambitious as l am — so they understand being busy, they understand business travel and they support growth.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

First of all, l think all women are beautiful in their own way. Some women are just really good at bringing that beauty forward and making their external beauty more visible. Do l think appearance is important? Absolutely! When you believe you look good, you feel good. When you feel good, you are confident, vibrant, and motivated. I place great emphasis on my appearance and start from the inside out by eating well and exercising then making sure my entire appearance is well thought through. I care about everything — what l wear, how my nails look, my shoes, my bag, my hair. It’s not superficial, it provides great value in every context. A wise person once told me “ the hair on your head and the soles on your feet, tell the woman in between.” Like it or not, first impressions count, people have an emotional reaction to each other’s appearance so you should definitely care about yours.

How is this similar or different for men?

I think it’s the same for men. Men should also care about their appearance. If you’ve noticed male grooming has really come up over the last decade. Men care about grooming and wearing fitted clothing too. Looking good will never close doors for you but not caring about your appearance might.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  1. Community — You need have the right people around you. People that are supportive and positive. My tribe is made up of men and women who also want to win and succeed so we understand each other. We all have moments where our confidence is low — make sure you have a community that pushes you and catches you when you fall. A community that will comfort you when you need it. I am part of many women’s groups and l find comfort in networking with women who are walking similar journeys.
  2. High Self-worth — By this l mean having high self-esteem and respect for yourself. It’s about being self-aware enough to recognize your strengths and the areas you need help. It’s about your values and what keeps you motivated and grounded. I am very clear on who l am and what l will and won’t do. What to say yes and no to. Finally with self-worth, l include managing your Imposter Syndrome — as women, we face so many challenges that we sometimes end up doubting that we can do it and we are worthy. Keep a mantra and remind yourself frequently that you are worthy, you are capable, and you are deserving.
  3. Quest/ Purpose — You need goals that are realistic and bigger than you are right now. If you are self-aware, you can set more realistic goals. My purpose is to grow within the technology industry and to live a healthy life that has a positive impact on others, complete with love and financial freedom. But with those big goals, you must set mini milestones — these mark progress so that you have lots of victories along the way and can celebrate. Celebrating milestones keeps you motivated. I have personally struggled with this one, l identify a milestone, then as soon as l achieve it, I’m on to the next thing. It’s important to make a conscious decision to stop and celebrate; l now have friends that hold me accountable to celebrate milestones. It also feels good to celebrate others.
  4. Fortitude — By this l mean determination and drive to succeed. This is not empty positivity, its unshakable resilience, courage, and strength. It’s the wisdom to adapt and know that even when things don’t go your way, there are lessons to be learnt and silver linings to be taken advantage of.
  5. Health & Wellness — Take care of your health and appearance. When you’re healthy and looking good, you feel good and possibly live longer. Make time to do the things you love and find fun. These things revitalize your mind and bring you back to life. Don’t be so absorbed in your career that you forget to live life. I can honestly say that many innovative ideas have come from moments when l am relaxed and enjoying something that has nothing to do with work. Burn out is real, sometimes you really need to step away from a situation to see it clearly, look at things from a different perspective and gain new ideas. I love golfing, travel and relaxing on my couch to good movie and a glass of red wine.

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.

OMG there are so many great people l would love to have breakfast with… but going with an immediate need l would have to say Garrett Camp or Travis Kalanick — the founders of uber. I am still in owe of how a simple idea for an app turned into this billion-dollar empire. I know the power smart technology and would love to learn how they achieved buy-in for their idea and the challenges they faced to execute.

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

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