Women in Tech: A Q and A With the Ladies Leading Our Global Strategies

by Amanda Halbritter, Senior Global Content Marketer, Rackspace Technology

Casey Shilling, Adrianna, Bustamante, Karen O'Reilly-Smith, Angela Logan-Bell at Rackspace Technology

International Women’s Day (IWD) was first celebrated more than a century ago. Held annually on March 8, IWD is a global day celebrating the social, economic, cultural, and political achievements made by female pioneers from every corner of the world. The day is also a call to action to help forge a more gender- equal world. One of the missions is “to elevate and advance gender parity in technology and celebrate the women forging innovation.” This year, Rackspace Technology® sat down, virtually, with a few of our women in tech to talk about modeling authentic leadership, amplifying female voices, and building professional networks. Take some time to read through each of the questions (Q) and answers (A), and find inspiration to help #BreakTheBias.  


Casey Shilling, Chief Marketing Officer 

Casey Shilling, Chief Marketing Officer, Rackspace Technology

Casey has a long history of growing brands and building strong workplace cultures. Before Rackspace Technology, she was Chief Marketing Officer at J. Hilburn, Zoës Kitchen, and VP of Marketing at The Container Store. She co-authored “Uncontainable: How Passion, Commitment, and Conscious Capitalism Built a Business Where Everyone Thrives” with the founder and former Chief Executive Officer (CEO) of The Container Store, Kip Tindell.


Q: How did you come to Rackspace Technology? 

A: A former colleague of mine who was an executive at the time at Rackspace Technology reached out to me. She thought that the company could really benefit from me, not only from my consumer brand marketing background but also my approach to communication and leadership. 

I had worked with her for most of my long tenure at The Container Store, and she said I don't know if we even have a role, but I just feel like you need to be here, Casey. The company really needed to grow its brand awareness of the company. So, I had some great conversations with the executive leadership team, and then the rest is history. I came over to help grow the brand and communications strategy, and now I'm the Chief Marketing Officer. 

Throughout my whole career, my goal has been to create a brand that when people hear their name, they go, oh my gosh, I love that company! I want them to say, “I love The Container Store!” “I love Zoe’s Kitchen!” and “I love Rackspace Technology!” It’s what fuels my soul as a marketer. I love building a story and a brand awareness where people are connected emotionally and feel that the company adds value to their life or business. 


Q: When creating a global marketing strategy for any organization – what are some of the key things to keep in mind to build a successful brand?

A: You must have a clear company strategy, and we do. Our five-point company strategy that we’ve communicated to Rackers is driving us to our goal - to be the best-in-class, pure play cloud solutions company. Next, you need to know who your customer is, and you need to be data-driven to determine the best way to engage with them.  From there, you design your marketing tactics and touchpoints to reach your goals. 

As a marketing team, we are working to build brand awareness of who Rackspace Technology is today, drive sales through lead generation and claim authority as an innovative thought leader in our industry. And for me, I think of every single Racker as a marketer. You grow and build a brand from the inside out, and our Rackers can be our biggest megaphone to help spread the good word of Rackspace.  

Communication is key here. Every person in the organization has to understand the company strategy, hold hands and drive towards our common goal. There can’t be any silos because if the one hand doesn't know what the other hand is doing, you're going to get mixed messages, and you'll get inconsistencies with the brand and our voice. 

For a global organization like Rackspace Technology, we must make sure that we're in lockstep with the marketing leaders and teams across the globe. We want to closely align our sales, product, and marketing teams so that we stay close to the pulse of the customer and provide a Fanatical Experience at every turn and touchpoint.  


Q: Like many leaders, you didn’t start in tech. For women interested in pivoting into the technology industry - what’s your advice to help them jump start or transition into a new career path?

A: Be brave! I think to grow, you have to be curious – you need to step outside of your comfort zone. You have to be resourceful and not afraid to ask questions. It doesn’t matter what level you are within a company. There are seriously no stupid questions. I think that’s how you build perspective when taking on a new role. 

And find mentors, don’t wait for someone to come to you and tell you that you need to be mentored. I’ve been really lucky to be surrounded by mentors who I like to call “Demanding Coaches.” You want to have a demanding coach in your life. That doesn’t mean that’s someone who yells at you or who’s militant or awful to you. Instead, a demanding coach is a leader and mentor who is demanding in a gracious way because they care about you and want to see you push yourself. 

If you think back, you can remember that coach or teacher that pushed you the hardest. Sometimes they make you go home and  question: “Why did they push me so hard to go that extra mile? Or ask me to play a position that’s not something I normally play.” It’s because they see something in you - something you didn’t even know that you had in you. I think having those mentors in your life will help you to try something you haven’t ever done before, to step into a role you’ve never been in before, or to go into an entirely different industry.  


Q: You’re speaking at the upcoming Women in Leadership Symposium on March 15. What are some of the things you’re looking forward to talking about at that event? (Theme being Paragon of Womanhood: Restoration, Reintegration, and Reemergence)

A: Each fantastic leader that’s a part of this panel is talking about a different topic. My theme is “Beyond the Balancing Act,” where I’ll be digging into the subject of work/life balance. Personally, and truthfully, I’ve never really prescribed to the word “balance.” I just don’t think it’s realistic for anybody passionate about their work and life.  

I believe it’s more about integrating all the things you want to accomplish in your life by focusing on the right things at the right time. You can be passionate about your job, so there’s a blur between work and play. A CEO (Kip Tindell from The Container Store) I worked closely with for a very long-time in my career used to ask, “was Monet working or playing when he painted the Water Lilies?” He would say, “Monet was doing what he was passionate about while enjoying it. He was doing what he loved.” 

You need to find a workplace that feels like home and surround yourself with people you love to get out of bed and work with every day. Find people who inspire you, which are better than you at some things. That’s motivating.  And when you need to make time to do the things that are important to you in your personal life, don’t be afraid to ask. Sometimes I think women feel like they can’t ask to do something as simple as taking time during work hours to attend a school function or volunteer at their child’s school. 

For some reason, we women put that on ourselves when we could have just made the ask. Women who are young in their careers or even people who've been around the block, like me, or people that are kind of in the middle of their career, we still hold ourselves back from doing that, and I don't know why sometimes. Let’s just have real talk. That is something I always tell the folks who report to me or on my teams. Let's be vulnerable, and if you work hard and the trust is there, we will find a way to make that work-life integration easier for you.  


Q: When you think about celebrating International Women’s Day, who are some women you look up to and have influenced your unique perspective?

A: I have a lot of women I’ve looked up to and followed throughout my career, and I keep a lot of leadership books and quotes around me all the time. I love to start meetings with a quote. I always say I'm the Ted Lasso of Rackspace Technology in some ways because I have positivity in my top five strengths, and I truly try to start the day with optimism and gratefulness. I try to lead that way as well. 

And I think in terms of women who have influenced that, it really started with my mom. It’s coming up on the year of her death, and we were very connected. I saw her go to work every day and be fulfilled by being a mom and having a career to provide for her family. She was a great role model. My mother always told me I could do and be anything I wanted - and I believed her. There was always that encouragement, and maybe some of my dreams were a little far-fetched, but I thought I could do anything, and it was because of her. 

I'm also surrounded by a very tight group of girlfriends who have seen me at my best and worst. They lift me up, but also aren’t afraid to be real and transparent with me when I need real feedback. When I think about another great mentor, I go back to Melissa Reiff, the former Chief Executive Officer of The Container Store. She was who I reported to for the longest part of my career, and she saw things in me that I didn’t even notice. She had an “everything matters” approach to leadership – from the small details to the big ones. She pushed me hard and helped expose me to opportunities and challenges that helped shape the leader I am today. 

I think we can all be mentors as women and not make it about competition, but more about contribution and collaboration. We're more powerful as a team than if we're trying to compete against each other. Instead, we should encourage and learn from each other. 


Adrianna Bustamante, Vice President of Global Alliances & Partnerships

Adrianna Bustamante, Vice President of Global Alliances & Partnerships, Rackspace Technology

Adrianna has a proven track record of building and optimizing strategies and partnership development across various industries. Before her fifteen years at Rackspace Technology, she worked in corporate communications for Twentieth Century Fox Home Entertainment. Additionally, she often serves as a subject matter expert while participating in speaking engagements, content development, and advisory roles. 


Q:How did you come to Rackspace Technology?

A: When I decided to move back to Texas from Los Angeles, I looked at Austin jobs. My background at that point had been in entertainment publicity, and I was interested in exploring other roles. Brooke Belasco Hernandez, “my ride or die,” worked at Rackspace and told me that they were opening an Austin office that would be sales focused. 

I didn’t have any technology experience, so I was unsure I would be an ideal candidate. She assured me that they cared more about getting the right talent and culture fit and that the company would help me learn the technology side. She talked about the importance and culture of Fanatical Support™, and that was something I understood! I’m big on a great customer experience and seek it out as a consumer. 

I was persistent in pursuing an entry-level sales role in the Q-Team/Lead gen team while also evaluating another opportunity in marketing in Austin. When I received the offer, I decided to take the chance on a new industry and choose Rackspace! 

At the time, Rackspace was very headquarter-centric, so I stayed in San Antonio and continued to take on new opportunities and roles. Also, San Antonio as a city was changing, and I had a new perspective and appreciation for my hometown. I typically find myself trail-blazing, and Rackspace has provided me with great opportunities to do that. 


Q:You’ve been a Racker for over 15 years! What advice do you have for women interested in growing their careers with an organization?

A: Build your internal and external network and know your strengths and passions; that’s when you are at your peak performance! Harness your peak performance to drive results and create your vision. You can use that to your advantage as your superpower. 

Also, don’t be afraid to raise your hand to tackle new challenges, opportunities, or pilots and share your ideas. I think it’s valuable to be proactive with your leaders and network to touch on these areas where you know you bring value and are at your best. It can help keep you top of mind when a new opportunity arises.   


Q:When building global alliances and partnerships – What are the building blocks for successful and long-term relationships with those organizations?

A: I believe building relationships and trust creates a strong partnership foundation. From there, you want to understand how each organization and key stakeholder will define success, what drives motivation, and know where you create value and differentiation. This foundation leads to a shared vision coupled with a strong joint plan to create something meaningful and impactful. 


Q:You were recently featured in  Hispanic Executive. How do you think other Latina women in technology can “amplify” their voice across this industry?

A: It’s important to show up and be a voice! Using your voice is the first step and creates an example for others. I also believe in paying it forward and finding ways to create opportunities for other Latinas to make their mark.  


Q:When you think about celebrating International Women’s Day, who are some women you look up to and that have influenced your unique perspective?

A: The first woman that comes to mind is Brené Brown. That woman gives you the straight talk and is real. She’s built an incredible career by owning her story and passion. She consistently inspires me and challenges me to think; I adore her, and the fact that she grew up in San Antonio is added goodness. 

Also, from my mother to grandmothers to aunts and cousins, I am fortunate to have women in my family who have given me valuable lessons and set examples for me – they likely have no idea what I take away from them. I cherish these nuggets and am always amused when I find myself emulating these ladies or putting their lessons to practice. 

I’m also a huge fan of Shakira. She’s a kindred spirit. I’ve been listening to her since I spent a summer in Mexico in high school, and her energy fuels me, and I can’t help but smile and want to dance when I hear her music. Never mind the fact that she’s a huge humanitarian, international superstar, speaks five languages, and recorded her first album at thirteen! She just makes me want to dance, and who doesn’t want to dance?! 


Karen O’Reilly-Smith, Chief Security Officer (CSO)

Karen O’Reilly-Smith, Chief Security Officer (CSO)

Karen has over twenty years focused on the practice of Information Security. Before Rackspace Technology, she worked for Barclays, Wells Fargo, IBM, and American Express. She has in-depth working experience in technology and operational re-engineering, along with her information security expertise. In addition, she has led global, multicultural teams across financial and technology services.    

Q:How did you come to Rackspace Technology?

A: I actually knew the previous CSO, and he called me up in 2018 and told me he was retiring, and Rackspace Technology was looking for a replacement. He asked if I would be interested. I was working at Aetna as the International Chief Information Security Officer (CISO) and doing challenging and interesting work. I turned him down at the time. 

However, he was persistent and eight months later called me back and said they were still looking for the right fit for a CSO and would I at least talk with the Chief Operations Officer (COO) for a short conversation. I agreed.  I had the conversation, liked where the company was going, and I was interested in the role. I accepted the position a few weeks later, and it’s been two and a half years, and I enjoy the role more every day.  My experience prepared me for this role and its challenges. I continue to look forward to maturing the Rackspace Technology security program by utilizing my deep knowledge and experiences.     

Q:You often speak at Cybersecurity events and were recently featured as a guest on Solve Live’s “Women in Tech” series. What’s the main piece of advice you have for women interested in pursuing a leadership role within security operations?

A: Go for it! Take the leap. A role in Cyber Security is a career, not a job, and it’s a role that is ever changing and evolving. So, if you like change, working in agile environments, thinking fast on your feet and outside the box, take the chance on Cyber Security, you will not regret it.    


Q:   When creating a global security roadmap for any organization – where do you start?

A: For me, I begin with accessing the current program and determining its maturity. Look at the Security program mission, roadmap, and metrics. Talk with current staff, peers, and partners. Most importantly, listen, listen, listen! You need to know where the program is to determine where it has to go. 

Once you gather all the input, you document a roadmap, preferably a three-year one. Then you share the roadmap and get buy-in and approval. The next step, start executing. Keep the roadmap ready and reviewed on a quarterly basis, Cyber Security environment changes rapidly, and you will need to adjust your plans as you go.     


Q:  Cybersecurity is such an essential pillar within tech. How important is it to network within the industry, and what advice do you have for women wanting to expand their network?

A: A network of peers, partners, and professionals is a must in any field and industry. I advise people to start building their network at their current company and get to know people within your team and outside of the group. Keep connected with them, even if you move on to another role or company in the future. Go to events within your field and make connections. Go up and talk to someone you heard speak that impressed you. Seek out a mentor because they’ll become lifelong friends.  


Q:When you think about International Women’s Day, who are some women you look up to and have influenced your unique perspective?

A: The number one person in my life who influenced me the most was my mom. She was a career woman in the 1950s at a time when most women did not work outside the home. She gave me very practical advice I still use today and pass on to my daughter, who is just starting her professional career, and mentees that I have the pleasure of working with. 

My mother's advice was to be passionate about what you do or find something else. Life is too short not to love what you do. She would advise me always to give 110% to the current role. She would say, “bring your whole self to the role.” She would always tell me to have a plan; that was the accountant in her. And lastly, she reminded me to enjoy the journey. It goes by fast.     


Angela Logan-Bell, Senior Director of Strategic Partnerships, Alliances & Marketing (APJ)

Angela Logan-Bell, Senior Director of Strategic Partnerships, Alliances & Marketing (APJ), Rackspace Technology

Angela has more than two decades of experience and deep connections across the ICT channel. Before Rackspace Technology, she worked for Optus, Dicker Data, Express Data and spent ten years at Ingram Micro. She has won two internal peer-voted Rackspace Technology awards and was a finalist in the ARN WIICTA awards in 2021. 


Q: How did you come to Rackspace Technology?

A: I knew I needed to future-proof my career and start learning and developing new skills and knowledge. Having spent nineteen years in IT Distributors, taking the step to Optus was very much a sideways one, if not a backwards step, but it was a calculated risk. A risk that saw me working directly with customers inside a large Telco-partner organization which gave me incredible insights into how customers were using cloud, engaging with cloud, and what their IT challenges were. 

There were some incredible learning experiences at Optus. While it was an individual contributor role and was a step down in compensation, it provided me clarity on what I love doing. I knew I needed to find a new role, and it gave me the experience to take on the position at Rackspace with confidence. Careers don’t always follow a linear trajectory. Sometimes, you need to deviate, trust your gut, and take yourself outside of your comfort zone to foster growth and development. It led me to Rackspace Technology, and I am incredibly grateful for that. 


Q: What’s the best piece of advice you have for young women developing their professional careers in technology?

A: I very strongly believe it's got a lot to do with your morals, values, ethics, and being true to your beliefs. You must be true to your standards. In the past, because women haven't had as much recognition of gender inequality, we were forced to make compromises to our values. 

For example, if we’re put in a less than ideal situation, we have to worry. If I speak up, I could feel repercussions. Is it going to impact my career? That ability to be true to your values is just so critical. If something has happened where I felt was completely wrong, I speak up from the core of my being. I've had some of the most impactful learning experiences by just speaking up. 

Whatever it is, if it doesn't feel right, it's important to speak up about that. Usually, you can address it with the person directly, and many times it can be a mea culpa moment. Sometimes a person will say something without realizing it and thinking it was just one of those harmless sorts of comments, but they’re not harmless at all. 


Q: An organization's culture is often an important component of professional success. How do you think women can gravitate to companies that they align with seamlessly? 

A: First, I would start by asking yourself: What kind of culture do you identify with, and what type of culture do you value? For me, the kinds of organizations that value honesty and sharing unique opinions mean they respect your knowledge. If they’re criticizing and constantly dismissing your ideas tells you that organization doesn't want to include you in the conversation, and that’s not a company you want to work for. 

And honestly, the role is just as important as the culture. Find a position that you enjoy, where the elements of that role allow the organization to get the best out of you. That’s how you can have an impact and get noticed. 

Sometimes you don't always know what that role will be, or it might not even exist today. I know it’s hard to visualize something if it doesn't exist, but what you can do is use those experiences or be clear on the things you don’t want to do that will get you closer to the proper role and closer to success.


Q: We just acquired Just Analytics from the Asia-Pacific and Japan (APJ) region, and I know you we’re in a lot of conversations about building that alliance. How do you think global organizations can utilize regional partnerships to their advantage?

A: One of the exciting things about Just Analytics coming aboard is they have quite a few female developers. We’ve really struggled to find female technical talent in the region. In fact, we have found it incredibly difficult. I think it’s an amazing opportunity for us to learn from what the team members at Just Analytics have accomplished and what they will achieve. They bring a lot of expertise surrounding data, and it’s made an impact on the region. 

Just Analytics comes with a lot of credibility and experience in a significant pillar of technology, which is unique to Rackspace Technology. We’re taking their expertise and capabilities and learning from what they’ve done for their customers and partnerships aids the rest of the APJ business. It’s exciting to dive deep into our key partnerships to deliver joint value for Rackspace Technology and partners like AWS, Microsoft, and Google. 


Q: When you think about celebrating International Women’s Day, who are some women you look up to and that have influenced your unique perspective?

A: The first woman that comes to mind is my grandmother. She was the matriarch of my family. She was born in 1910 and had a very strong opinion that wasn’t necessarily popular at the time. It was really a feat for her sometimes, and I know that the majority of that was because of social norms, but I see my grandmother as a strong role model. 

Another interesting woman I admire is Julia Gillard, the first female Prime Minister of Australia. I always wanted to get into politics, but I soon realized that there would be a lot of compromises that I would find very hard for me to accept. I didn't identify with all her politics, but I think she did an incredible job while being held to a different standard. What she accomplished with a hung parliament along with the abuse and vitriol, you know, critiquing her image - she just rose above it. The way she's handled herself the whole way through it is completely inspirational. 

I also believe that men have played a massive role in helping me be the best woman I can be. I lost my dad in January, and he supported me unconditionally and propelled me to believe in myself. And when you have that unconditional belief and support, it really impacts your confidence. You know, it doesn't matter where you get that support. Whether it’s another female or male leader in your life, encouragement should be gender neutral.

These are just a few of the innovative female leaders at Rackspace Technology. Throughout March, our Chief Technology Evangelist Jeff DeVerter will be interviewing more women in tech on his bi-weekly Solve: Cloud Talk lives. A recent episode featured Natalie Silva, Director of our Analyst and Public Relations. You can hear her insights, along with other women from across our organization, on Tuesdays & Thursdays at 8:30 a.m. (CT). Tune-in on March 22 to hear from Holly Windham, our Chief Legal and People Officer, and March 29 to learn more about Casey Shilling, our Chief Marketing Officer. 

Follow us on LinkedIn, YouTube, and Twitter for more details.

Learn more about how our culture empowers women in technology to #BreakTheBias. 

Come Work for a Company Committed to Advancing Women in Technology