Alex Doonanco is the CEO and co-founder of careCycle, where he leads the development of AI voice teams that have transformed Medicare agency operations. Since launching in October 2024, careCycle has engaged in more than 400,000 conversations with seniors, helping agencies reduce churn, improve retention and deliver consistent, high-quality service. Alex brings deep expertise in conversational AI and healthcare technology from his time as the first U.S. hire and go-to-market lead at AI Rudder, where he designed large-scale contact center automation projects across multiple B2C industries.

“Opportunities in healthcare go to those who can bridge the gap between innovation and trust.” — Alex Doonanco

How does CareCycle approach designing AI systems that truly change the member experience?

We start with the moments that matter most to members. That might be choosing a plan, understanding new benefits or getting help with an unexpected medical bill. Our Inquiries system allows AI and human agents to collaborate on complex questions so members always get accurate answers. Today we support more than 300,000 beneficiaries and offer capabilities like voice cloning for independent agents and regional accent customization to build familiarity in local markets. If a question requires a licensed agent the transition is seamless. This approach creates consistency and trust while allowing agencies to offer round-the-clock support without expanding headcount.

Medicare churn is notoriously high. How big is the problem you are solving?

We deliver up to a 37 percent improvement in retention for our clients. During the 2024 AEP we helped a leading FMO write more than $2 million in renewals. A major driver of churn is the “orphan client” problem where members lose their original agents and lack a consistent point of contact. By keeping members informed and engaged from day one through renewal season, agencies protect that investment and strengthen member loyalty.

What is driving that churn?

Too often, members hear from their agency only when they are being sold a plan. After that, the relationship goes quiet. High acquisition costs can also push agencies to lower standards and rely on aggressive marketing, which often results in less engaged members. We help agencies replace that gap with timely, relevant outreach such as welcome calls and carrier approval notifications that make members feel valued from the start. These touchpoints, combined with AI support, reduce agent talk time by 20 percent per sale while improving outcomes.

In a regulated high-trust industry, how can compliance become a competitive edge?

In Medicare the ability to demonstrate compliance is as important as closing a sale. Our platform is HIPAA compliant, follows SMS compliance protocols and operates strictly within CMS-approved use cases. Every interaction is documented for audit purposes. Agencies that can show regulators and partners that each exchange meets the rules build credibility and win more business.

How is AI adoption in healthcare evolving and what role will it play in the next five years?

Healthcare is moving toward continuous engagement instead of one-time transactions. We launched in October 2024 and have grown quickly, handling more than 29,000 ACA renewal calls in a single day. Our mission for 2025 is to give Medicare agents back 1 million hours by automating routine interactions and enabling proactive outreach. In the coming years it will be normal for a member to get plan reminders, health tips and answers instantly through AI systems that work alongside human teams.

You are a Y Combinator-backed founder. How has that shaped your journey?

I joined the Winter 2025 Y Combinator batch after building my background in conversational AI at AI Rudder. Y Combinator reinforced the importance of focus. We proved our model with large agencies, learned what scaled and distilled those insights into a version that smaller agencies could adopt in days. In just months we facilitated more than 1 million conversations with beneficiaries, validating that the model could scale without losing quality.

What market trends are shaping the future for Medicare agencies?

The population turning 65 is growing, competition for members is increasing and regulations are evolving to protect consumers. At the same time, member expectations are being shaped by other industries where service is fast and personalized. Agencies that can combine compliance, efficiency and personalization will be in the strongest position to grow.

How would you describe your leadership style when navigating such a fast-changing market?

I make decisions by starting with the impact on the member and working backward. In healthcare, trust is earned over time and lost in moments. That means being deliberate about product changes, how we support agencies and how we handle member interactions. I encourage the team to think about the long-term relationships our technology enables, not just the immediate transaction.

Final thought for Citybiz readers?

Opportunities in healthcare go to those who can bridge the gap between innovation and trust. The combination of AI capabilities and human expertise is the path forward and agencies that embrace it will be the ones that thrive.

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