Nicole Yelsey: Building Kindness into Leadership and AI

Nicole Yelsey’s story is a bridge between heritage, leadership, and the future of technology. As Co-Founder and COO of KindWorks.AI, she is leading efforts to embed kindness directly into the ways we work and connect. Her professional background spans Fortune 100 companies and startups, and we discussed how her early life and values continue to shape her leadership and her vision for AI.

Nicole grew up in northern Illinois with parents who were “accidental entrepreneurs.” Her father, raised Amish, chose not to join the church and was initially shunned, even to the point where his parents did not attend his wedding. Her mother, raised Mennonite, made a deliberate effort to keep family connections alive. She would stop by relatives’ homes on long drives and insist on preserving ties, even when traditions made it difficult. Over time, those walls broke down, not by chance but through her mother’s persistent acts of kindness—stopping by relatives’ homes and refusing to let estrangement be permanent. That resilience and strength became a lasting model for Nicole.

Her career path brought her into marketing, brand, and business development, but leadership became the recurring theme. She recalls learning from two very different managers—one a servant leader who made time to listen and care, and another whose distant style created barriers. The lesson for Nicole was that kindness in leadership shows up in everyday actions, in listening, and in approaching even difficult conversations with care. It shaped her own approach as a leader, grounding her in the belief that care and accountability are not opposites but partners.

When asked what investing in kindness means, she described it as intentionality. “It is both important and urgent,” she explained. For Nicole, kindness is how leaders prioritize their time and their impact and how each one of us chose to show up every day. She shared a story of having her car broken into and her bag stolen and the bag had significant personal value to her. The computer and wallet were gone, but a stranger found the bag discarded under a tree and found her business card inside and took the time to contact her and return it. That small act of effort and thoughtfulness has stayed with her as a reminder of how people can choose to go out of their way to help others.

Today, Nicole brings that philosophy into technology through KindWorks.AI. Their first product, Beni, is an AI agent that integrates into Microsoft Teams, Slack, and WhatsApp to encourage daily acts of kindness. Whether it is guiding someone through a hard conversation with empathy or suggesting small gestures like reaching out to a neighbor, Beni treats kindness as a practice to build like a muscle. Nicole sees this as essential not just for workplaces but for humanity itself.

She also stresses the urgency of ethical leadership in AI. The “move fast and break things” culture, she warns, cannot be the norm for technologies that hold such power over our lives. Nicole is deliberate about confronting risks rather than ignoring them, insisting that clarity, safety, and ethics must sit alongside innovation if AI is to serve humanity.

“Kindness is paramount in anything we do. We have start by showing kindness to ourselves, others and our environment.”

Nicole Yelsey’s work shows how intentional kindness can be operationalized—in leadership decisions, in AI product design, and in daily team habits. Keep an eye out for more interviews.