Kyile Stair, a lifelong advocate for people, has always been drawn to the power of human connection. As the Chief People Officer at Litmos, a global leader in learning solutions, she’s dedicated to fostering a workplace culture where employees feel valued, empowered, and inspired.
With a proven track record in HR leadership roles at SAP and Target, Kyile brings a wealth of experience to her role. She’s passionate about creating inclusive and equitable work environments where individuals can thrive. Beyond her professional pursuits, Kyile is an ardent supporter of women in leadership and underrepresented groups. She believes in the importance of authenticity and encourages everyone to bring their whole selves to work.
In our latest Faces, meet Kyile Stair.
How did you get your start in the field?
From the very beginning of my undergraduate studies, I knew I wanted to pursue a career in human resources, which led me to take a significant number of HR-focused classes. Upon graduation, I joined Target in an HR role and simultaneously pursued my master’s degree. This experience helped me strengthen my business acumen beyond the retail industry, expand my professional network, lay a solid foundation for my career in HR, and further ignited my passion for empowering others in the workplace.
Who is/was your biggest influence in the industry?
I’ve been influenced by thought leaders like Adam Grant and Dave Ulrich. Adam’s work on organizational psychology has shaped how I think about building supportive workplace cultures, while Dave’s insights into human capital and leadership have been valuable to my strategic HR approach. Additionally, I’ve been fortunate to have a former leader who believed in my potential and put my name forward for a role that truly transformed my career trajectory. This experience deepened my belief that people thrive when they lift each other up.
What’s your best mistake and what did you learn from it?
Early in my career, just after I graduated and started my role at Target, I naively believed that a more autocratic approach was the best way to manage people. Unfortunately, this mindset strained relationships, and I developed a reputation for being unapproachable. It was a humbling experience, and I quickly realized that leadership is not about control but about collaboration and empathy. When I moved into a new role, it gave me the opportunity to reset, rebuild my brand, and apply those lessons by focusing on building strong, trusting relationships with my team. That experience has shaped how I lead today.
What’s your favorite part about working in the industry? What’s your least favorite part, and how would you change it?
My favorite part of working in this industry is the opportunity to support others in reaching their career goals and achieving success. Whether it’s through learning and development, mentoring, or coaching, I love seeing people grow and thrive. It’s incredibly rewarding to be in a role where you can make a tangible difference in someone’s professional journey, and that’s something I get to experience every day in the people and L&D space.
On the flip side, my least favorite part is navigating the constantly evolving compliance requirements and regulations. While it can be challenging, I’ve found that working for an organization like Litmos, which focuses on compliance training content, makes it easier to stay informed about these changes. Partnering with experts who keep a finger on the pulse of regulatory changes is crucial, and it’s a strategy that helps ensure we’re always ahead of the curve.
It sounds like through your experience you really care about people, and you want to help them feel safe and comfortable, which is important in the industry. Please elaborate here.
Taking initiative in DE&I is a top passion and priority of mine. DE&I is comprehensive, and organizations have to be intentional in building their programs and integrating them into all business processes. Organizations also have to make sure their employees understand the value of diversity and the metrics and data behind it. At Litmos, we’ve built an inclusive and people-centric workplace, which is measured in our bi-annual employee engagement survey and consistently earns top-tier scores.
As for L&D’s connections to DE&I, Litmos offers hundreds of DE&I courses and training for all levels of an organization. These trainings cover a wide range of topics including neurodiversity, inclusive behaviors, unconscious bias, violence, bullying & harassment prevention, LGBTQ+ inclusion, and more. Inside Litmos, these courses play a big role in our culture of continuous learning – where we include them in our onboarding, compliance training, manager enablement, and more.
How can HR most effectively demonstrate its value to the leadership team?
It’s crucial to understand the business and financial metrics that support a healthy organization. This may look different based on your industry and the products you sell, but two critical questions remain constant: “How does my company make money?” and “How does the HR budget impact our profitability?” HR should focus on showcasing how our processes and programs align with the organization’s vision and goals. When presenting recommendations, we need to emphasize how these initiatives will lead to a more engaged workforce, ultimately driving better business outcomes. Additionally, taking a proactive role in change management initiatives can further illustrate how the people function is integral to the organization’s success. People’s success is our success.
Where do you see the industry heading in five years? Or are you seeing any current trends?
In terms of employee training and Edtech, three of the top trends I foresee in the industry are the (1) use of hybrid training programs, (2) microlearning, and (3) upskilling and reskilling.
1: One of my top industry predictions is that in-person learning isn’t going away anytime soon. While online learning increased significantly during COVID, it’s not the only answer for training. For example, our latest HR leadership playbook found that 36% of employees prefer in-person training for its direct interaction and immediate feedback. With that, one of the hardest decisions for L&D leaders to make is deciding which format is best for employees – the answer is hybrid training programs. Hybrid training programs can be designed to meet the varied needs of employees and adapted to suit unique circumstances, goals, and expectations.
2: Microlearning is slowly becoming a more popular approach to training where people can learn in small blocks of time. Since most employees don’t have endless amounts of time to engage in training, microlearning provides a suitable format for delivering instruction. Many organizations choose microlearning because it allows for flexibility – with the ability to deliver microlearning across a variety of devices, learners have the option to choose when and where they engage with the content.
3. Upskilling and Reskilling: The World Economic Forum estimates that by 2028, nearly 44% of the global workforce will need reskilling. This rapid change, driven by technological advancements and economic shifts, has created a significant skills gap. Brandon Hall Group’s report, “Mind the Gap: Learning and Development Solutions for Skill Shortages,” reveals that upskilling and reskilling are top priorities for HCM leaders. Nearly 9 in 10 organizations are hiring or preparing to hire for new roles, emphasizing the urgent need to bridge the skills gap. Organizations are just starting to scratch the surface when using L&D as a strategic tool for their growth strategy, and I expect this trend to accelerate in the future.
What are you most proud of?
I’m most proud of the teams I’ve built and the people I’ve surrounded myself with — people who are exceptional at what they do. I believe in setting a positive example by working hard while also prioritizing your own well-being. Following the divestiture of Litmos from SAP, I’m especially proud of what we’ve built and created as a global, stand-alone organization in just under two years. Implementing our HR tech stack, establishing HR processes and policies, and creating and implementing L&D and talent management programs – all from the ground up – means there’s never been a dull moment!
Do you have any advice for people entering the profession?
My advice for those entering the profession is to embrace every day as a new opportunity to learn. You’ll be working with people who have unique needs and perspectives, so it’s essential to keep an open mind. Always be willing to problem-solve and adapt, whether it’s navigating the challenges of an abrupt transition to remote work or upskilling and reskilling in the age of AI. Learn from your colleagues and mentors, as you won’t have all the answers — nobody does. Continuous learning is key to thriving in this field, so stay curious and proactive in your development.