Gyde Acquires We Know Medicare to Strengthen Medicare Leadership and Accelerate AI-Native Brokerage Platform
Austin, Texas — May 18, 2026 — Gyde, the next-generation, AI-native brokerage platform, today announced it has acquired We Know Medicare ("WKM"), a leading Medicare insurance agency known for its high-performing Medicare engine, strong leadership, and deep downline network. WKM’s owner, Mike Mathweg joins Gyde as a Partner and remains CEO of We Know Medicare alongside the entire WKM team.
The acquisition deepens Gyde's Medicare distribution footprint from coast to coast and brings one of the industry's most innovative Medicare leaders onto the Gyde team. The partnership is poised to accelerate WKM’s rapid momentum, which grew 4x in the past 8 months through a series of strategic acquisitions — a pace that will continue as Gyde and WKM continue to scale through partner agencies.
Under Mike Mathweg’s leadership, We Know Medicare has built a reputation for educating and empowering brokers and agency owners to amplify their growth with structure, transparency, and technology. Its downline network spans over 300 agents, primarily in the Pacific Northwest and Texas, serving clients across 44 states.
Under the partnership, WKM will use Gyde's AI platform to make their brokers more productive than ever—automating enrollment workflows, expanding capacity during Annual Enrollment, lifting renewal rates, and unlocking new cross-selling into ancillary and wealth products. The platform is designed to work alongside WKM's existing systems, not replace them, so brokers see more support, not more software.
"Mike and the team at We Know Medicare have done something rare in this industry. They've built a Medicare business that wins on education, trust, and partnership, not just on lead volume," said Will Johnson, Co-Founder and CEO of Gyde. "Bringing WKM into the Gyde platform lets us pair that foundation with AI-native tools that remove administrative drag, so their brokers can spend more time doing what they do best: helping seniors make confident coverage decisions. This is the kind of agency we want to build alongside."
The acquisition of WKM follows the announcements of the acquisition of leading Medicare agency Avid Health, founded by Gerrick Diaz, and Consumer FMO Benavest, led by Joe Gannon and Regina Sara over the past month, showing that Gyde’s owner-centric partnership model is attracting some of the industry’s most ambitious leaders.
"I’m thrilled to be formally partnered with Mike again after working together in the past and watching him operate up close over the years. He’s one of the most ambitious builders in the space, and our partnership positions him to continue acquiring and growing Medicare business with We Know Medicare under the Gyde umbrella,” said co-founder and COO Sam Wiener. "With modern AI infrastructure accelerating operations and ensuring best in class client service, an owner like Mike is perfectly positioned to focus on what he does best: buying and integrating Medicare books of business into a next generation, AI-enabled Medicare business. Together we’ll set the standard for what a Medicare agency can look like when technology works for the broker instead of against them."
WKM will continue to operate under the We Know Medicare 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.
"This partnership was an easy yes," said Mike Mathweg, CEO of We Know Medicare. "Having built and sold a Medicare agency before, I knew what I was looking for: leadership with experience, integrity and a vision for AI transformation that can add rocket fuel to our growth. Gyde’s commitment to brokers, and the quality of the tools they're building, is unmatched in the market today. WKM is still WKM—same team, same leadership, same commitment to the clients and brokers who rely on us. What's new is that we now have the capital, technology, and operational support to grow faster and go further than we could alone. I'm excited for what the next chapter looks like for our team, our brokers, and the seniors we serve."
The acquisition follows Gyde's recent public launch with $60 million in funding led by Lightspeed and this third acquisition announcement in 2026 anchors Gyde's strategy to partner with and acquire leading insurance agencies while equipping them with an AI-native platform that automates administrative complexity and helps brokers deliver more proactive guidance across insurance, health, and wealth decisions.
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 We Know Medicare
We Know Medicare is a Medicare Insurance Brokerage with licensed insurance professionals representing Medicare health care products and a suite of ancillary products to meet senior adults’ unique coverage needs. Headquartered near Seattle, Washington, the company has over 300 agents serving clients across 44 states.
Media Contact
Laura Metzger
FAQ
AI for insurance agencies is technology that automates client communication, back-office workflows, and data analysis so brokers can serve more clients without sacrificing personalized service. Modern AI handles routine tasks like benefits questions, document processing, and renewal outreach in the background while licensed brokers focus on advisory work. Platforms like GydeOS deliver this as a single AI-native operating system rather than a patchwork of point solutions.
Insurance agencies use AI across three core pillars: client service, back-office admin, and business intelligence. AI agents answer routine client questions by text and voice, automate onboarding and compliance workflows, and analyze book-of-business data to surface retention risks and cross-sell opportunities. The result is brokers who can support more clients with deeper, more proactive service.
Health insurance companies and agencies use automation to improve efficiency in three primary ways: client communication, document and compliance workflows, and proactive retention outreach. Automated agents respond to routine client inquiries by SMS and voice without staff involvement. Document workflows handle onboarding, policy changes, and compliance tracking in the background. Automated outreach flags renewal windows, retention risks, and coverage gaps so brokers can act before clients churn.
No. AI is remarkably efficient at managing data, following logic, and resolving routine tasks, but it lacks the three things that define a great broker: judgment, advocacy, and empathy. AI replaces administrative tasks, so brokers can focus on the high-level advisory work that requires a human license.
Not when you partner with Gyde. We understand that most agency owners don't have the time to act as their own IT department. We’ve already done the heavy lifting of building, evaluating and integrating the best AI tools for insurance agents. When you join Gyde, you aren't building a tech stack from scratch; you are bringing your agency into a personalized, AI-native environment with the support of experienced partners.
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