The Problem with Unhelpful Robots
Startup founder Alex Doonanco follows a simple philosophy: a helpful robot is better than an unhelpful human. Yet there’s a third, more problematic option that dominates today’s landscape.
“People are used to an unhelpful robot, and that’s worse than anything,” Doonanco tells Upstarts. This observation has driven his mission to revolutionize how artificial intelligence serves one of America’s most vulnerable populations: senior citizens navigating the complex Medicare system.
The challenge isn’t just about automation—it’s about creating meaningful, personalized interactions that genuinely help people understand their healthcare options and make informed decisions about their coverage.
Building Voice AI for Medicare Insurance
Over the past year, Doonanco has developed careCycle, a startup building voice AI tools specifically designed for companies selling Medicare health insurance plans to senior citizens. The platform targets a critical gap in the healthcare technology market where automation often fails to deliver genuine value.
The Market Opportunity
For insurance brokers and agencies selling Medicare plans, careCycle provides sophisticated pre-screening capabilities and personalization tools that significantly boost sales conversion rates and customer retention in an intensely competitive marketplace. The Medicare insurance industry represents tens of billions of dollars annually, creating enormous pressure on call centers to generate qualified leads through aggressive marketing tactics across platforms like Facebook.
This aggressive approach often creates a fundamental mismatch between consumer expectations and reality. Doonanco recounts hearing calls where confused consumers inquired about “DOGE giving out dividends”—illustrating the widespread confusion that plagues the current system.
For senior citizens who need healthcare coverage, careCycle promises a dramatically improved experience through personalized communication that understands their specific plan details and individual needs, while delivering faster, more accurate answers to critical coverage questions.
Early Success and Traction
The results speak volumes about careCycle’s product-market fit. By August 2024, the platform had already processed one million conversations, remarkably doubling that volume within just the following month. The startup achieved $1 million in annual recurring revenue (ARR) with an incredibly lean team of only four full-time employees supported by an “army” of part-time contractors.
These impressive metrics demonstrate that careCycle has identified a genuine pain point in the Medicare sales ecosystem and built technology that effectively addresses it.
From Road Trip to Y Combinator Success
The Genesis of CareCycle
CareCycle’s origin story began last fall during an unlikely three-day road trip. Doonanco, a Canadian citizen and fluent Mandarin speaker, was driving back from the Bay Area to renew his visa when inspiration struck. His background included various analyst and advisory roles, plus leading U.S. expansion for AI Rudder, a Singapore-based voice AI automation startup.
During that road trip, Doonanco called his technical friend Evan Roubekas with a compelling pitch: “I’ll teach you voice AI so we can attack this market together.” The pair identified that approximately 65% of Medicare brokers and agencies still consisted of small businesses and independent operators—a fragmented market ripe for technological disruption.
While startups like J.D. Vance-backed Chapter Advisory focused on helping consumers select plans, Doonanco saw a bigger opportunity: building AI voice tools specifically for the advisors themselves.
Product Features and Benefits
CareCycle initially launched as a solution for handling incoming and after-hours calls, offering automated appointment booking, relevance-based pre-screening, and personalized follow-up communications. The platform enables automated check-ins during the weeks following enrollment, while also providing a 24/7 hotline for mid-cycle coverage questions—preventing seniors from being susceptible to unnecessary plan switching.
“What I find so compelling about voice as the final user interface is that there’s no learning curve,” Doonanco explains. “You can ask in natural language, just like you learned when you were a baby. You don’t need to click a bunch of buttons, or log in to your phone.”
The value proposition proved compelling immediately: businesses as small as 5 to 10 employees willingly pay $10,000 monthly for the service. CareCycle generated $70,000 in revenue during its very first month of operation, eventually leading to acceptance into Y Combinator’s prestigious accelerator program.
Scaling Beyond Voice AI
The CRM Vision
CareCycle harbors ambitious plans beyond voice automation. Today, the Y Combinator alum launched a comprehensive new product alongside announcing $2 million in funding from investors including Strike Capital and Pioneer Fund, an alumni fund specifically for YC founders.
The startup’s biggest operational challenge involves integrating its tools across customers’ existing software ecosystems, including CRM platforms like HubSpot and Salesforce. These integrations require significant time investment and forward-deployed engineering resources, pushing the company toward a managed services model rather than pure technology provision.
Doonanco’s solution? Build their own CRM system specifically optimized for Medicare businesses. His vision encompasses creating a complete system of record that not only maintains conversational context but also handles customer records, call dialing, and all related sales activities. “We don’t need to charge by the seat for the CRM; we can just give it to them for free,” he declares boldly.
The CEO draws a parallel to Perplexity competing against Google—an audacious comparison that reveals the startup’s massive ambitions.
Funding and Growth
While $2 million represents a relatively modest round by current AI startup standards, it provides careCycle with resources to execute on its ambitious CRM vision. Louis van Hove, an investor at Strike Capital, believes the startup’s niche focus provides competitive advantage against horizontal CRM players.
“I think it’s going to be very difficult for horizontal players to offer that kind of complexity or feature options,” van Hove notes. However, he acknowledges the journey has only just begun. “I think they’re well positioned, but at this stage, it’s really all about the founder. Alex is boots on the ground.”
Ethics and Future of Voice AI
Maintaining Trust with Seniors
The ethical implications of deploying voice AI with elderly populations cannot be ignored. While careCycle announces its AI agent at the start of every call, concerns remain about whether all seniors fully comprehend or remember they’re interacting with artificial intelligence rather than a human representative.
“Philosophically, that should give people pause,” Doonanco admits candidly. The startup maintains strict guardrails on tool usage, deliberately avoiding an open platform where customers could build any type of voice assistant without oversight.
Advice for AI Startups
For entrepreneurs considering voice AI opportunities in other verticals, Doonanco offers pragmatic guidance. First, ensure your tool will benefit from advancing large language models rather than face them as competition—making regulated industries ideal starting points. Second, address the fundamental question: “Are you building something that actually changes the unit economics of the business you’re selling to?”
As AI voice tools proliferate across healthcare, life sciences, and phone-dependent sales markets, careCycle’s trajectory provides a valuable playbook for vertical-specific AI implementation. The startup’s early traction demonstrates that helpful robots can indeed beat unhelpful humans—when designed thoughtfully for specific use cases.
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