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Founder Hamza Mostafa and engineering team members will join the Medicare guidance provider, which already uses AI to support its advisors.
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Chapter is bringing Ridgeway founder Hamza Mostafa and the startup’s engineering team into a business that already uses AI behind licensed Medicare advisors. The acquisition is framed as a way to improve guidance and develop products for consequential retirement decisions, not as a product launch. Mostafa previously built and evaluated OpenAI systems including ChatGPT Agent and ChatGPT Deep Research; Chapter’s reported scaling gains from backend AI have no specified growth measure.
Chapter announced the acquisition on October 22, 2026; it did not disclose the purchase price.
Ridgeway had previously raised $2.8 million from Emergence Capital and Susa Ventures; that funding was not the acquisition price.
Chapter describes AI as supporting licensed advisors by helping them ask questions and surface answers for personalized Medicare recommendations.
Chapter is adding engineers to build AI products for retirees, bringing experience from OpenAI’s agent systems into its Medicare guidance business. The company announced on October 22, 2026, that it had acquired applied AI startup Ridgeway. Founder Hamza Mostafa and members of Ridgeway’s engineering team will join Chapter through the deal.
The purchase price was not disclosed. Chapter presented the acquisition as a way to improve its Medicare guidance and develop additional products supporting consequential decisions in retirement, rather than announcing a new product available now.
Before founding Ridgeway, Mostafa built and evaluated agent systems at OpenAI, including ChatGPT Agent and ChatGPT Deep Research, according to the acquisition release. His background brings experience developing and assessing those systems to Chapter’s planned work for older adults.
Ridgeway previously raised $2.8 million from Emergence Capital and Susa Ventures. That figure describes the startup’s earlier venture funding, not the amount Chapter paid to acquire it.
Chapter CEO and co-founder Cobi Blumenfeld-Gantz tied the purchase to recruiting engineers for products serving seniors. He described Mostafa and his team as exceptional and argued that older Americans are poorly served by the technology industry.
Seniors are the most skeptical demographic when it comes to AI, but they also have the most to gain from advances in technology.
Hamza Mostafa, Ridgeway founder, in the acquisition announcement
Chapter says it already uses AI to help advisors ask the right questions and surface answers for seniors seeking Medicare guidance. Its platform supports licensed advisors in delivering personalized coverage recommendations. The described workflow places AI behind the advisor, rather than presenting it as a replacement for that person.
The company also credits its backend AI workflows with enabling it to scale by several multiples each year while keeping corporate headcount nearly flat. It did not identify the growth measure behind that claim, so the statement offers no precise comparison of revenue, customer volume or advisor productivity.
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