Kristy McCann
Kristy McCann is a CEO, founder, and strategic advisor in the HR technology and education space, with over 20 years of experience leading organizational transformation, human capital strategy, and workforce development initiatives. She is the Founder of 127 Ventures and a former Co-Founder and CEO of SkillCycle, an HR tech company built to democratize skills development by connecting performance, learning, and engagement into a unified, AI-enabled system. Her work focuses on building scalable solutions that help organizations translate feedback and people data into real-time development outcomes.
Throughout her career, Kristy has held senior leadership roles across major organizations including Pearson Education and Constant Contact, where she led large-scale digital transformation, change management, and organizational development efforts. Her expertise spans go-to-market strategy, product evolution, M&A integration, and HR technology innovation. She has been recognized as a 3x Inc. 5000 honoree and has built and scaled companies to significant valuation and growth, including leading a venture-backed HR tech company that achieved rapid year-over-year expansion.
Today, Kristy serves as a strategic advisor, keynote speaker, and HR tech innovator, working with education and workforce technology companies to improve how organizations develop talent and adapt to AI-driven change. She is passionate about building ethical, human-centered systems that prioritize learning, trust, and workforce empowerment. Her mission is centered on ensuring that individuals across all industries and backgrounds have access to the skills and development opportunities needed to succeed in the modern economy.
• Enneagram Certification
• DISC Certification
• Prosci Change Management Certification
• Pragmatic Marketing Model Certification
• Saint Joseph’s University — Bachelor of Science (B.S.), Human Resources
• University of Scranton — Master of Arts (M.A.), Organizational Development & Business
• Inc 5000 Fastest Growing Company (2023 and 2025)
• Inc Best Employee Company (2024)
• ASPCA Volunteer Network
• LGBTQIA Board Membership
• Forbes Coaches Council
• Animal welfare advocacy
• ASPCA Volunteer (Animal Welfare)
• LGBTQIA Advocacy and Community Support
What do you attribute your success to?
I attribute my success to a combination of my upbringing, my curiosity, and my commitment to continuous learning and growth. Growing up with limited resources taught me resilience and determination. Throughout my career, I’ve been fortunate to learn from influential leaders and mentors who helped shape my thinking and leadership approach. Most importantly, I’ve stayed committed to my North Star—ensuring that people have the skills they need to succeed in their work and careers.
What’s the best career advice you’ve ever received?
The best career advice I’ve ever received is: “If you’re going to bet on anyone, bet on yourself.”
What advice would you give to young women entering your industry?
My advice to young women entering this industry is to stand up, not stand down. Do not let gender or any other label define your potential. Your value comes from your intelligence, resilience, and ability to grow and lead. It is important to come together, support one another, and avoid division. Real change happens when we collectively raise our voices and advocate for equity at every level—locally, nationally, and globally.
What are the biggest challenges or opportunities in your field right now?
One of the biggest challenges in my field is the rapid evolution of AI and how it is being adopted without proper structure, ethics, or change management frameworks. While AI presents enormous opportunities for workforce development and skills democratization, it also introduces risks such as inequality, misuse, and lack of governance.
The greatest opportunity lies in building responsible AI systems that integrate learning, performance, and development in a way that supports people rather than replaces them. Organizations that successfully implement ethical, human-centered AI transformation will lead the future of work.
What values are most important to you in your work and personal life?
Integrity is my core value—it guides everything I do. I also deeply value curiosity, critical thinking, and the ability to pause and reflect before acting. I believe in operating with honesty, transparency, and a strong sense of responsibility toward others. At the center of my work and life is a commitment to service—helping people grow, develop, and access the skills they need to succeed.
Locations
127 Ventures
Ormond Beach, FL 32176