Influential Women Features Whitney Skye O’Brien: A Trailblazer in Tech, Customer Engagement, and Advocacy
Chicago, Illinois — Whitney O’Brien is a full-stack leader across marketing, customer success, and operations. Best known for her success in email marketing and her pioneering work in customer engagement through Rich Communication Services (RCS) technology, Whitney has consistently demonstrated bold, data-driven leadership while inspiring others to break barriers.
Born in Mississippi and raised in a family marked by addiction and abuse, Whitney left home as a teenager and rebuilt her life from the ground up. Working full-time, she earned her GED and later graduated Summa Cum Laude with a Bachelor of Science from Southern New Hampshire University, achieving a 3.97 GPA. Her early life proved that grit, perseverance, and self-determination would define her journey.
Whitney broke into the tech industry in an entry-level role and quickly 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 over $40 million in incremental annual revenue. This success set the tone for her career: she would combine creativity, analytics, and boldness to deliver transformative results.
At Level Access, Whitney drove strategies that fueled rapid growth, helping the company surpass a $100 million valuation and earn recognition in the Gartner® Market Guide, Forrester Wave™, and Inc. 5000. Along the way, she embraced 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 emerging leaders.
Currently serving as Head of Customer Success and Operations at nativeMsg, Whitney leads in the emerging field of RCS, helping organizations revolutionize how they connect with customers. Her expertise combines operational insight, technical know-how, and a deep understanding of human interaction to design experiences that are both innovative and impactful.
Whitney’s early life has also shaped her commitment to advocacy, storytelling, and justice. She has contributed to organizations such as CrimeCon, Code Your Dreams, Amplify Allyship, Code Social, and Deaf Kids Code, using her voice and experience to create meaningful change in her community.
Whitney attributes her success to resilience and grit. Growing up without role models, she was guided more by what she didn’t want to become than by anyone showing her the way. She emphasizes that circumstances do not define a person—every step forward and every success earned belongs entirely to the individual who fought for it.
The best career advice Whitney received is to bet on herself and advocate for her own growth. By embracing opportunities before feeling fully “ready,” she advanced from an entry-level role to a founding team member at GoDaddy Social, shaping onboarding processes and scaling a new product line from launch. “Advocating for myself and believing that I belonged in the room changed the trajectory of my career,” she emphasizes.
Whitney encourages young women entering the tech industry to take initiative and create their own opportunities. She challenges the notion of “earning a seat at the table,” noting that many traditional spaces were never built with underrepresented voices in mind. Instead, she advises building new tables, fostering collaboration, and leading on one’s own terms. By doing so, women can ensure that their perspectives are not only heard but valued, creating environments that empower others to succeed as well.
Whitney identifies one of the biggest challenges in technology today as the rapid growth of AI without clear governance. While AI offers tremendous innovation, it also introduces risks related to bias, ethics, and responsible usage. Whitney views this as an opportunity as well: when implemented thoughtfully, AI can enhance personalization, streamline decision-making, and free teams from repetitive tasks to focus on strategy and creativity. Her approach emphasizes balance, advocating for frameworks that empower people rather than replace them or limit their potential.
Whitney’s core values—education, advocacy, and giving back—guide both her professional and personal life. She believes education and awareness enable people to adapt and grow with confidence. Advocacy ensures that underrepresented perspectives are amplified, while giving back through mentoring and volunteering allows her to enact her values in practice. For Whitney, success is measured not only by personal accomplishments but also by the ability to lift others alongside her.
Whitney Skye O’Brien’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 drive lasting change.
Learn More about Whitney Skye O’Brien:
Through her Influential Women profile, https://influentialwomen.com/connect/whitney-obrien
Influential Women
Influential Women provides a platform where women from all backgrounds can connect, share their perspectives, and create content that empowers themselves and others. Through storytelling, thought leadership, and creative expression, Influential Women amplifies voices that inspire change.
From Overcoming Adversity to Pioneering Innovation in RCS and Marketing Strategies
Chicago, Illinois — Whitney O’Brien is a full-stack leader across marketing, customer success, and operations. Best known for her success in email marketing and her pioneering work in customer engagement through Rich Communication Services (RCS) technology, Whitney has consistently demonstrated bold, data-driven leadership while inspiring others to break barriers.
Born in Mississippi and raised in a family marked by addiction and abuse, Whitney left home as a teenager and rebuilt her life from the ground up. Working full-time, she earned her GED and later graduated Summa Cum Laude with a Bachelor of Science from Southern New Hampshire University, achieving a 3.97 GPA. Her early life proved that grit, perseverance, and self-determination would define her journey.
Whitney broke into the tech industry in an entry-level role and quickly 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 over $40 million in incremental annual revenue. This success set the tone for her career: she would combine creativity, analytics, and boldness to deliver transformative results.
At Level Access, Whitney drove strategies that fueled rapid growth, helping the company surpass a $100 million valuation and earn recognition in the Gartner® Market Guide, Forrester Wave™, and Inc. 5000. Along the way, she embraced 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 emerging leaders.
Currently serving as Head of Customer Success and Operations at nativeMsg, Whitney leads in the emerging field of RCS, helping organizations revolutionize how they connect with customers. Her expertise combines operational insight, technical know-how, and a deep understanding of human interaction to design experiences that are both innovative and impactful.
Whitney’s early life has also shaped her commitment to advocacy, storytelling, and justice. She has contributed to organizations such as CrimeCon, Code Your Dreams, Amplify Allyship, Code Social, and Deaf Kids Code, using her voice and experience to create meaningful change in her community.
Whitney attributes her success to resilience and grit. Growing up without role models, she was guided more by what she didn’t want to become than by anyone showing her the way. She emphasizes that circumstances do not define a person—every step forward and every success earned belongs entirely to the individual who fought for it.
The best career advice Whitney received is to bet on herself and advocate for her own growth. By embracing opportunities before feeling fully “ready,” she advanced from an entry-level role to a founding team member at GoDaddy Social, shaping onboarding processes and scaling a new product line from launch. “Advocating for myself and believing that I belonged in the room changed the trajectory of my career,” she emphasizes.
Whitney encourages young women entering the tech industry to take initiative and create their own opportunities. She challenges the notion of “earning a seat at the table,” noting that many traditional spaces were never built with underrepresented voices in mind. Instead, she advises building new tables, fostering collaboration, and leading on one’s own terms. By doing so, women can ensure that their perspectives are not only heard but valued, creating environments that empower others to succeed as well.
Whitney identifies one of the biggest challenges in technology today as the rapid growth of AI without clear governance. While AI offers tremendous innovation, it also introduces risks related to bias, ethics, and responsible usage. Whitney views this as an opportunity as well: when implemented thoughtfully, AI can enhance personalization, streamline decision-making, and free teams from repetitive tasks to focus on strategy and creativity. Her approach emphasizes balance, advocating for frameworks that empower people rather than replace them or limit their potential.
Whitney’s core values—education, advocacy, and giving back—guide both her professional and personal life. She believes education and awareness enable people to adapt and grow with confidence. Advocacy ensures that underrepresented perspectives are amplified, while giving back through mentoring and volunteering allows her to enact her values in practice. For Whitney, success is measured not only by personal accomplishments but also by the ability to lift others alongside her.
Whitney Skye O’Brien’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 drive lasting change.
Learn More about Whitney Skye O’Brien:
Through her Influential Women profile, https://influentialwomen.com/connect/whitney-obrien
Influential Women
Influential Women provides a platform where women from all backgrounds can connect, share their perspectives, and create content that empowers themselves and others. Through storytelling, thought leadership, and creative expression, Influential Women amplifies voices that inspire change.
Editorial Team
Influential Women
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