Ashley Hyman – Celebrating Women
Ashley Hyman and I met twenty-six years ago at cheerleading practice in Middle America. I sat on a bench by my shy self, eager to feel included and like I belonged, as teenage, pubescent children so often do. “Hi!” a cute, curly-haired brunette greeted me. Ashley introduced herself, and we became fast friends.
Her simple act of kindness and inclusion could arguably move mountains if all of us were willing to extend that type of greeting to our neighbor, the person in line at the grocery store, or the homeless individual sleeping on the sidewalk near your favorite café. Before you go engaging in the welcoming behavior this world needs right now, let’s get to know more about Ashley Hyman – VP of customer experience.
Through a series of insightful questions, we’ll dive into her story, perspectives, and experiences. Get ready for a fresh look at the richness of not only the soul of womanhood but the brilliance and breadth of the hard-working mother.
ASHLEY HYMAN
You've got 2 minutes to tell me your life story
How do you respond?
I grew up in Kansas, but I knew early on that hard work and academics were my ticket to something bigger. One summer, I found my way to UCSD in San Diego, fell in love with the city, and made it my home after graduation. Grad school led me to my husband, and for the first time, I truly felt like I belonged.
My career took off with a research role, but my real breakthrough came when I led Customer Success at Portfolium. That experience opened the doors to SaaS, where I thrived—combining my passions for teaching, learning, and helping people.
The founders of that company later started Drata, one of the fastest-growing startups ever, and they trusted me to build something from the ground up. Today, with over 7,000 customers and over 100 employees within the org I built, I’ve proven to myself that I belong—and that I can do anything.
What moment shaped your identity as a woman and how does it guide you today?
I was laid off during maternity leave from a job I loved, but it turned out to be a gift. I spent over nine months with my daughter, building an unbreakable bond while reevaluating my priorities.
The timing, during COVID, also meant my husband was working from home, allowing us to navigate this new chapter together. That period helped us solidify our family dynamic and define how we function as a unit of three.
How has society's view of women evolved, and what barriers still need to be addressed?
Society has made progress in recognizing women as leaders, but we’ve yet to create environments that fully support mothers in balancing both roles with equal respect. From parental leave to flexible schedules, workplace structures still fall short.
Additionally, while we encourage women to lead, those who do are often labeled “difficult” or “aggressive.” I’ve even been advised to use more emojis to ensure my tone appears “friendly”—a clear sign that biases persist.
Can you share a time when you felt underestimated or overlooked because of your gender, and how you responded to that challenge?
For most of my career, I was fortunate to work with colleagues—primarily men—who treated me as an equal, valued my skills, and lifted me up. Because of this, I once dismissed the idea that gender bias played a role in the workplace. That changed at one point when I found myself in a situation where my ideas and opinions carried less weight simply because they came from me—a woman.
It was one of the most frustrating and disheartening experiences of my life. At first, I let it silence me, reverting to the quiet girl who followed rather than led. But thanks to a strong community that refused to let my light be dimmed—people who spoke my name in rooms I wasn’t in—I found the strength to speak up, stand my ground, and ultimately remove myself from that negative situation.
What does empowerment mean to you, and how do you foster it in yourself and other women?
True empowerment comes from surrounding yourself with people who value your opinion, respect your knowledge, and want to see you succeed. But that doesn’t mean they always agree with you. Real empowerment is being in a space where healthy debate is encouraged, disagreements are met with respect, and mutual trust remains intact.
At Drata, we built a culture where questioning ideas and engaging in thoughtful debate was not just accepted but expected. I believe that openness played a key role in our rapid growth and success—and it also forged some of my strongest friendships.
Now, I actively work to create that same environment for other women in the workplace. Unfortunately, many of us have encountered women who exclude, take credit for others’ work, or tear others down to elevate themselves. I’ve found that doing the opposite—fostering collaboration, sharing recognition, and lifting others up—has led to far greater success. No one thrives alone, and “kingdom-building” often leaves you isolated with a crumbling castle. True fulfillment comes from creating a space where people feel valued, supported, and empowered to grow together.
What advice would you give your younger self about womanhood, strength, and self-worth?
If I could speak to my younger self, I’d tell her to stop worrying so much about what others think. I spent too much time holding back—afraid to say the wrong thing, so I said nothing at all. I followed rather than led, shrinking myself to fit expectations. In doing so, I missed opportunities to discover my passions, build deeper connections, and truly value myself.
"True fulfillment comes from creating a space where people feel valued, supported, and empowered to grow together."
What would you let go of to feel lighter and more at ease each day?
I wish I could let go of perfection as a measure of success or accomplishment. The pressure to overperform or exceed others’ expectations likely holds me back and makes me more cautious to take chances or explore more creative ideas.
Which woman, whether personal or public, inspires you, and why?
I’m a huge Michelle Obama fan. I admire her unwavering confidence, integrity, and authenticity. She stays true to her beliefs despite challenges and openly shares her struggles—in her career, relationships, and motherhood—rather than projecting unattainable perfection. I also deeply connected with her advocacy for physical activity and nutrition as First Lady.
Ashley, thank you from the bottom of my heart for participating in the Celebrating Women series for The Road Linds Travels. I’m immensely grateful for the chance to share your insights and perspectives on the distinctive yet shared journey of navigating this world as a woman. My hope is that you and others continue inspiring and uplifting the women and girls around us, initiating these important conversations and creating platforms for those who have yet to find their voices.
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