Whitney Skye O'Brien
Whitney O’Brien is a full-stack leader across marketing, customer success, and operations, most known for her success in email marketing and, more recently, pioneering customer engagement with RCS technology. Born in Mississippi and raised in a family marked by addiction and abuse, she left home as a teenager and rebuilt her life from the ground up. While working full time, she earned her GED and later graduated summa cum laude from Southern New Hampshire University—proof early on that grit and perseverance would define her journey.
Breaking into tech in an entry-level role, Whitney refused to let her background, title, or tenure limit her impact. Within eight months, she was tapped to help build a new onboarding program at GoDaddy. Soon after, she designed a promotional experiment that generated $40M+ in incremental revenue. That success set the tone for her career: bold, data-driven, and unafraid to challenge expectations.
At Level Access, Whitney drove strategies that fueled rapid growth and helped the company surpass a $100M valuation—earning recognition in the Gartner® Market Guide, Forrester Wave™, and the Inc. 5000.
Along the way, she embraced personal advice from Fara Howard, GoDaddy’s CMO, to “stay curious”—a principle she continues to live by as she builds teams, influences industries, and mentors future leaders.
Now serving as Head of Customer Success and Operations at nativeMsg, Whitney leads in the emerging field of Rich Communication Services (RCS), helping organizations transform how they connect with customers.
Her early life also shaped her commitment to storytelling, advocacy, and justice—inspiring her work with CrimeCon as well as her volunteer efforts with Code Your Dreams, Amplify Allyship, Code Social, and Deaf Kids Code.
Whitney’s journey—from leaving home with nothing to shaping the future of communication technology—embodies her belief in resilience, curiosity, and advocacy as forces that create lasting change.
• Women Transforming Tech: Breaking Bias
• Developing Effective Teams (BUS1200)
• Project Management (PM1001)
• Visual Communications (VISCOMM1001)
• HubSpot: Email Marketing
• Google: Advanced Analytics
• Southern New Hampshire University - BSB
What do you attribute your success to?
Resilience and grit. I grew up in difficult circumstances, and that meant I had to figure out life on my own. That resilience and the willingness to keep moving forward no matter what is the foundation of my success.
What’s the best career advice you’ve ever received?
The best career advice I’ve ever received was to always bet on myself and to advocate for myself. Early in my career, I realized that if I waited until I felt fully ‘ready,’ I would hold myself back. Instead, I started saying yes to opportunities, even when they felt bigger than me, and I learned how to grow into them. That mindset is how I went from an entry-level role to becoming a founding member of the team that built out onboarding for GoDaddy Social, a new product line, helping design processes and strategies that scaled the solution from launch. Advocating for myself and believing that I belonged in the room changed the trajectory of my career.
What advice would you give to young women entering your industry?
When you enter tech, people will tell you to focus on earning your seat at the table. But here’s the truth: those tables weren’t built for us. Don’t wait for permission to join. Build your own table. Create new spaces where your voice is not just heard but valued. Invite others in, make room for collaboration, and show what leadership looks like on your own terms. We have the power to design the table, set the agenda, and change the entire room.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in tech right now is the rapid rise of AI and the lack of clear governance around it. We’re seeing incredible innovation, but the rules, standards, and guardrails haven’t caught up. That creates real risks around bias, ethics, and how responsibly these tools are applied. But it’s also one of the greatest opportunities. When used thoughtfully, AI can unlock personalization at scale, accelerate decision-making, and free teams from repetitive work so they can focus on strategy and creativity. For me, the key is balance: embracing the benefits of AI while also advocating for responsible frameworks that ensure the technology is used to empower people to do things we've never been able to before, not replace people or disadvantage them.
What values are most important to you in your work and personal life?
The values most important to me are education, advocacy, and giving back. I believe education and awareness empower people to grow, adapt, and navigate change with confidence. Using my voice to champion others, create opportunities, and make sure underrepresented perspectives are heard. Giving back through mentoring and volunteering allows me to live those values in action, because success isn’t just about what I accomplish, it’s about how I help others rise with me.