How Cedar & Twilio Are Rebuilding the Patient Experience with AI with Dugan Winkie, Head of Commercial Strategy at Cedar

May 14, 2025

Dugan Winkie, Head of Commercial Strategy at Cedar, is at the forefront of innovating the healthcare experience. He discusses how AI is transforming patient interactions, particularly through their conversational agent, Cora, which provides empathetic support and helps navigate complex billing. Winkie emphasizes the importance of bridging gaps between providers and payers while ensuring data quality fosters trust. His insights reveal how tech like AI can overhaul traditional healthcare challenges, ultimately enhancing patient satisfaction in a complicated system.

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INSIGHT

AI Tackles Healthcare Billing Confusion

Healthcare billing is confusing due to information silos and complexity.
Conversational AI can help patients navigate billing by connecting disparate data points.

INSIGHT

Billing Questions Drive AI Innovation

Patients frequently call with billing questions beyond just payment.
Healthcare billing innovation includes tailored patient engagement and dynamic workflows like abandoned cart nudges.

INSIGHT

Data Drives AI Efficacy in Healthcare

The key to effective AI in healthcare billing is leveraging diverse, integrated data.
AI must act as a problem solver to address patient confusion and varied needs.

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In this episode of Builders Wanted, we sit down with Dugan Winkie, Head of Commercial Strategy at Cedar, to explore how AI is reshaping one of the most emotionally complex industries: healthcare. From frustrating call center experiences to opaque billing processes, Dugan breaks down how Cedar is reimagining patient engagement with conversational AI, real-time data, and a builder’s mindset.

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Key Takeaways:

Strategic innovation involves closely monitoring market feedback, especially given significant operational cost constraints, regulatory uncertainties, and budget cuts.
The use of conversational AI ensures that patients receive timely and accurate assistance, which reduces dependency on call centers and enhances the overall patient experience.
Health systems must balance using innovative technologies while adhering to strict regulatory frameworks to ensure a seamless and secure patient financial experience.

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“ There is a lot of information silos, simultaneously, where we're expecting patients to know how to navigate a very complex system. And we think conversational AI and agentic AI is a great manifestation where we can leverage a lot of our core competency and network connections to help answer those patients' questions in a way that is delightful.” – Dugan Winkie

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Episode Timestamps:

‍*(02:10) - The boldest thing Cedar is building right now

‍*(03:52) - How Cedar is using AI to humanize the patient financial experience

‍*(14:24) - Recent patient behaviors that pushed Cedar to rethink the billing experience

‍*(23:11) - How Cedar designed its AI agent, Kora, to be helpful and empathetic to patients

‍*(31:10) - How Cedar is balancing AI innovation and healthcare regulations

‍*(35:40) - How AI has already improved the patient journey

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Links:

Connect with Dugan on LinkedIn

Connect with Kailey on LinkedIn

Learn more about Caspian Studios

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Builders Wanted is brought to you by Twilio – the Customer Engagement Platform that helps builders turn real-time data into meaningful customer experiences. More than 320,000 businesses trust Twilio to transform signals into connections—and connections into revenue. Ready to build what’s next? Learn more at twilio.com.