The announcement marks the next stage of Relate’s growth as the company expands its platform, customer base, and vision for using AI to make meaningful development part of the conversations people are already having every day.
McCann Flynn is a longtime HR technology founder, operator, investor, and people leader who has spent more than 25 years at the intersection of people, culture, and technology. She previously co-founded and served as CEO of SkillCycle, where she raised more than $15 million and helped scale the company through rapid growth with Inc 5000 growth recognition over multiple years. Her career also includes senior HR and transformation roles across organizations including Pearson, Constant Contact, MoneyLion, Richemont, and Western Asset Management.
As Co-Founder, McCann Flynn will work alongside Relate’s existing founding team to accelerate customer growth, strategic partnerships, fundraising, product strategy, and market expansion, while bringing the voice of HR leaders and enterprise buyers directly into the company’s roadmap.
“Relate has everything I look for in a company: the people, the potential, the product, the passion, and a genuinely huge problem worth solving,” said McCann Flynn. “Every day, conversations shape relationships with customers, prospects, employees, and managers. Relate has the opportunity to turn those moments into continuous development and stronger relationships at scale. I’m incredibly excited to join this team as a co-founder and help build what comes next.”
McCann Flynn’s appointment comes during a period of growing momentum for Relate. The company was recently recognized by G2 as a Best New Software Product for 2026 and continues to expand its technology and reach. Most recently, Relate introduced Vocal Intelligence, extending its analysis beyond transcripts to include factors such as tone, energy, pace, humor, and conversational dynamics.
“Kristy has a powerful combination of founder, operator, buyer and evangelist experience,” said Tom Keenan, Co-Founder of Relate. “She understands what it takes to build a company, but she also understands what it takes for new technology to earn trust inside an organization. That’s incredibly important for where Relate is going.”
