Wisdom Unlocked 🔓✨ Career Lessons from Leading Women: A Conversation with Cynthia Carpenter, SVP of People for DigitalOcean
November 14, 2024 / /
- Could you start by introducing yourself—your name and what you do?
I’m Cynthia Carpenter, and I am the SVP of People for DigitalOcean, a global cloud computing company that helps developers and small-to-medium businesses build software that changes the world. - How did your career begin, and how did you get to where you are today?
I started out as an Analyst at Starz—even before Starz launched. I was employee #16, and during the four years I worked there, we grew exponentially. Thanks to a nudge from John Sie, one of the first and most influential things I did was to join the WICT Network (at the time, it was called WIC—Women in Cable), where I immediately learned the value of building relationships and connections with women leaders across the Cable industry. My path to overseeing the people function, like most career journeys, has featured many twists and turns. I spent most of my career in marketing and product management in the cable and technology space, and I shifted into human resources in 2016, when Charter merged with Time Warner Cable and Brighthouse. My boss at the time was Rich DiGeronimo, who asked me to take on the HR lead role for the Product & Technology organization. Without his belief in me, I would never have made that move. I seized the opportunity to apply my marketing, product management, and leadership experience to a new discipline, and I haven’t looked back since! - How have you seen the workplace shift since you started your career? What are the most significant changes you’ve observed?
Since launching my career, I have observed two big shifts in how we work. First, technology has changed the rhythm, the media, and the formality with which we work. When I first started, we barely used email. We talked on the phone and held meetings in person, and we printed everything (sorry, trees!). Because business was primarily done in person, people were outfitted to do that business—for women, it usually meant skirts (with pantyhose), heels, make-up—and a more formal tone of interacting. There was respect for hierarchy and a social agreement that what happened outside the office stayed outside the office. The idea of “empathetic leadership” wasn’t really a thing.
Second, thanks to technology, the ability to work remotely has changed everything from the boundaries between home and office to the way in which we interact. Slack, Teams, and other forms of instant messaging have deformalized conversations and removed boundaries between senior leaders and the organization. In my early career, I would never have imagined using an emoji in communicating with the CEO! While I see some of this as progress, I’ve also observed how it’s impacted the opportunity for early-career people to learn how to advance and how to gain executive presence. - Conversely, what aspects of the workplace have remained constant in your experience?
The value of building relationships is as important as ever. Especially for organizations that are highly distributed or heavily remote, developing connections is key to facilitating productive work. Building and nurturing relationships outside your company is as important as developing relationships within your company. My network of former colleagues and friends is gold. I rely on them for ideas, advice, sometimes for sharing frustration, and other times just for a good laugh. - Storytime! We’d love to hear about a pivotal moment or decision that shaped your career. It can be a success or a challenge—what stands out to you, and how have you changed because of it?
I’ve learned the most from the challenging moments when I’ve realized that I have the strength, support, and courage to do something bigger than I thought I could. Even before I started my career, I knew I wanted to be a mom. One of the biggest decisions I made was to become a mom AND to work outside the home. My husband Daniel and I decided that he would be the primary parent who stayed home when I went back to work after 6 weeks of maternity leave. Now, we have two grown-up daughters who have been the beneficiaries of having a strong dad who was deeply invested in raising them and a strong mom who was as deeply invested in our parenting partnership, showing them it’s possible to be both a mom and a leader at work. At the time, we made that choice, it was very unconventional, and I love that we were pioneers in that regard.
Another pivotal moment was the one I referred to earlier when I shifted from overseeing the Business Product portfolio at Charter to overseeing HR for the Product & Technology organization. The common theme during any change: you cannot do it alone. Often we might think that asking for help or support from others around you is a sign of weakness or an admission that you don’t have what it takes. I believe that asking for help is brave, and it’s a key to success. - Navigating work-life balance can be challenging and often more difficult for women. How have you managed this throughout your career?
If you’ve ever tried standing on one foot, you know you can’t stay that way for very long without wobbling. As with physical balance, it’s super hard to maintain a steady state of work-life balance. Sometimes we can get caught in the idea that all the things we do have to be done perfectly and held in balance. Not only does that take a lot of energy, but it also can feel overwhelming when we believe we must do all the things exactly right.
When I get overwhelmed, I think of the various important aspects of my life as glass or paper plates that I am spinning all at once. The glass plates are breakable and cannot fall, while the paper plates will float to the ground, and I can pick them up later. At any given time, a big project at work that cannot fall on the floor may qualify as a glass plate, while the same may also be true for a personal commitment to a family member or friend. Making purposeful decisions about how to prioritize the things that cannot fall on the floor helps keep me focused on what I must do, where I must be, and what I must deliver. I try to remember to focus on the present and to remember to ask for help when I have several glass plates spinning at once. - We encourage everyone, particularly women, to seek mentorship and guidance from leaders in their fields. Who has been your mentor along your journey, and how have they influenced your career?
Throughout my career, I have been fortunate to know and work with incredible people who I consider part of my personal board of advisors. The defining characteristic is that I am able to feel safe with each of them and say, “I don’t know.” In return, they have pushed me outside of my comfort zone by telling me a truth I may not have wanted to face or by encouraging me to do something I did not think possible.
My first mentor was Colleen Abdoulah, who (literally) pushed me on stage to deliver an award on behalf of the WICT Rocky Mountain chapter. If you know Colleen, this story doesn’t surprise you. From that awkward moment, I learned how to think on my feet and (ironically) to enjoy public speaking.
Later, I gained a wonderful mentor in my former Time Warner boss Dan O’Brien, who I still call for advice when I’m making big career moves. Kim Martin is another fabulous boss and now a friend and mentor, and who is someone I call when I need advice on influencing and gathering support. Gemma Toner is a constant source of encouragement (and nudging), and Ann Carlsen and Jana Henthorn have been long-time mentors and friends who have guided me on being a breadwinner-mom-executive.
Robyn Tolva, Elena Ritchie, and Jodi Robinson made my transition to HR and my time at Charter one of the best chapters of my career, and we still connect and seek each other’s guidance and support. Keely Buchanan is a constant cheerleader who challenges me to be brave and who reminds me, “You’ve got this!”
Tracy Baumgartner and Sarah Eder are my pod when things get challenging, as well as for lots of laughter. My most constant and steady mentors are my husband and daughters, who know me better than anyone. - What’s one piece of advice you would give your younger self when you were starting?
When my daughter was about 8, she tucked a note into my briefcase, and I have it framed and sitting on my desk. It says, “Dear Mommy, Thank you for being awesome.” I would tell my younger self to build my own self-confidence by reminding myself I’m awesome, the way I do for others around me.
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