Dec 09, 2025
HealthTech veterans join League as company sets sights on 100M users
Today we announced the appointment of two seasoned industry veterans to League’s executive leadership team: Chris Lyon joins as Chief Revenue Officer (CRO) and Michele Oliveto joins as Chief Delivery Officer (CDO).
The appointments come at a pivotal moment as League scales our global healthcare-as-a-platform strategy and aims to surpass 100M contracted users in the near future. This growth is fueled by international demand for AI-powered healthcare solutions that offer personalization at scale—like League Agent Teams™ for benefits navigation, care gap closure and health coaching.
Lyon and Oliveto will be instrumental in ushering in the next phase of the company’s growth, focusing on expanding market share among payers and health systems while ensuring seamless, high-impact implementations for League’s global customer base which includes Manulife, Quest Diagnostics, TELUS and Medibank.
Both executives bring decades of experience navigating the technical and regulatory intricacies of the healthcare sector.
Chris Lyon (Chief Revenue Officer) joins League with a distinguished track record of scaling high-growth healthcare technology companies (formerly with Workday, Model N). He specializes in navigating long-cycle enterprise sales, building predictability, and forming strategic alliances across the entire healthcare ecosystem. Under his leadership, companies have successfully scaled from $100M to $500M in annual revenue.
Lyon will oversee all aspects of League’s revenue generation, including global sales, partner growth, and customer success. His focus will be on accelerating the adoption of the League platform for AI-powered member and patient engagement.
Michele Oliveto (Chief Delivery Officer) is an expert in healthcare operations and digital transformation with 30+ years of experience (formerly with HealthEdge). Having led 500 person global delivery teams, Oliveto brings extensive experience in managing multi-year, multi-stakeholder roadmaps that touch millions of members. She has a proven ability to translate complex technology into functional, user-centric healthcare solutions that scale.
Oliveto will lead League’s professional services and implementation teams. Her mission is to ensure that League’s complex, large-scale deployments deliver immediate value, high member engagement, and long-term clinical outcomes for partners through proven and sustainable delivery models and AI-native technologies.
“Since day one, our mission has been to deliver personalized digital experiences that empower people with their health,” said Mike Serbinis, Founder and CEO of League. “With the rapid advancements in AI, this is now within reach and we need leaders who understand the grit and complexity required to transform this industry. Chris and Michele are world-class operators who share our vision. Their expertise will be a force multiplier for our growth and, more importantly, for the value we provide to our customers and their members.”
With this expansion of League’s executive team, Andrew Dubowec, who has served as Chief Growth Officer since 2021, will step into the role of Chief Business Officer. Dubowec will partner with League’s executive team and Board of Directors on strategic growth, revenue acceleration and enterprise value creation — including new market development, AI products, and M&A — helping to shape the company’s next decade.
These appointments follow other recent strategic hires including Senior Vice Presidents: Jordan Christensen (AI & Data Engineering) and Joel Finlayson (International Growth). League continues to grow our team and is hiring across the United States, Canada, the UK and Australia.
About League
Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and healthcare innovators build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including HCSC, Manulife, TELUS, and Medibank.