Gyde Acquires Osborne Insurance Services to Bring AI-Enabled Growth to a Trusted, Family-Run Agency

Austin, Texas — June 25, 2026 — Gyde, the leading AI-native brokerage platform, today announced it has acquired Osborne Insurance Services, a Raleigh, North Carolina-based, family-run agency known for deep community roots and a reputation built over nearly 30 years of personal, relationship-driven client service across ACA and Medicare. Osborne's CEO, Michael Osborne Jr., joins Gyde as a Partner and continues to lead Osborne alongside the entire team.

The acquisition extends Gyde's distribution footprint into the Carolinas and brings onto the Gyde team an experienced leader and producer who understands today’s clients needs and what it takes to meet them. As a boutique shop specializing in individual health plans, Osborne has earned its growth through long-term relationships, high retention, and the trust that comes from being a local fixture in Raleigh since it was founded by Michael Osborne Sr. in 1997.

Under Michael Osborne Jr.’s leadership in recent years, the high touch service model started to limit the agency’s ability to grow. As a family-run business, the firm's capacity was consumed by the daily reality of serving clients well: renewals, enrollment paperwork, and the administrative load that comes with doing right by every household. There were more clients to serve, but no capacity to take on additional work. "We were doing everything the right way, and it was working, but it meant we'd maxed out," said Michael Osborne Jr. "We could either stay exactly the size we are forever, or find a way to equip our team to work much more efficiently."

As part of Gyde’s growing network of leading agencies, Osborne will use Gyde's AI platform to make its brokers dramatically more productive — automating enrollment workflows, cross-selling to fill coverage gaps, expanding capacity during peak periods, lifting renewal rates, and freeing the team to spend more time with clients and the community they serve. The platform is designed to work in the background alongside Osborne's existing systems, so brokers see more support, not more software.

This partnership comes just before an enrollment season that is predicted to be one of the most demanding the industry has seen. The ACA Open Enrollment Period faces a shorter window and new requirements that add time to every application, while Medicare carriers continue to exit markets and adjust plan designs, driving more plan-shopping and more hands-on work per client. Brokers will face more to do in less time—exactly the kind of administrative drag Gyde's platform is built to absorb.

"Osborne is the kind of agency that inspired Sam and me to start Gyde in the first place: trusted, local, family-run, and there for people when it counts," said Will Johnson, Co-Founder and CEO of Gyde. "When we founded Gyde, the mission was to make sure agencies exactly like this one could grow without losing what makes them special. What Michael and his family have earned in their community is irreplaceable. Our job is to take everything that's working and remove the ceiling on it. This is the kind of partner we imagined from day one."

"What drew me to Gyde wasn't about an acquisition— it's because of what they're building," said Michael Osborne Jr., CEO of Osborne. "We've spent 30 years earning our clients' trust by showing up for them personally, and I was never going to trade that for scale. Gyde is building an AI-native foundation that takes the administrative weight off brokers so they can do more of the work that actually matters. That’s a foundation I want my team building on for the long run. With the next ACA and Medicare enrollment seasons shaping up to be the busiest on record, that timing couldn't be better. We're still Osborne Insurance Services. Our family and team will still be here, but now we're building toward a future we couldn't have reached alone, powered by Gyde."

"Osborne has the experience, relationships, and the reputation; what we bring is the technical and operational horsepower to scale it," said Sam Wiener, Co-Founder and COO of Gyde. "By automating the enrollment, client service, and renewal workflows that consume a boutique team's time, and layering in modern AI automation for the back office, we free Michael and his brokers to focus on what they do best. We're not just preserving what Osborne is today. We're building for the next generation, together."

Osborne will continue to operate under the Osborne brand, presented as "powered by Gyde." Day-to-day operations, carrier relationships, commissions, and contracting remain unchanged — a deliberate choice to preserve what's already working while layering in new capabilities over time.

The acquisition adds to a growing roster of leading agencies joining Gyde's owner-centric partnership model. As the industry braces for an unusually demanding enrollment cycle, Gyde is actively working with its downline and acquired agency partners to prepare for what's ahead — equipping brokers with an AI-native platform that automates administrative complexity and helps them deliver more proactive guidance across insurance, health, and wealth decisions.

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About Gyde
Gyde is an AI-native brokerage headquartered in Austin, Texas, with offices in New York City. Built for modern insurance professionals, Gyde combines advanced artificial intelligence with broker-first tools and operational support to streamline client servicing, renewals, and growth at scale. The Gyde platform enables brokers to grow faster and operate more efficiently while delivering comprehensive insurance, health, and wealth solutions.

About Osborne Insurance Services
Osborne is a family-run boutique insurance agency headquartered in Raleigh, North Carolina, specializing in ACA and Medicare coverage. Founded in 1997 by Michael Osborne Sr., the company has helped thousands of people secure marketplace and Medicare insurance coverage. Today, the company is led by CEO Michael Osborne Jr. and a team of experienced insurance professionals.