Munich Startup: What problem does your solution address?
Oliver Diekmann, Co-Founder and CEO: Around 70 percent of relevant knowledge in companies is not documented – it exists in the heads of the people who work there. When these people retire, resign, or a company is handed over, this knowledge is lost forever. We call that corporate dementia. By 2030, 6.5 million baby boomers will leave the German job market, and around 545,000 companies face handover by 2029, according to KfW Research. Wingmaite secures this implicit knowledge and makes it usable for employees and AI before it’s gone.
Munich Startup: What can only you do today?
Oliver Diekmann: We’re not building the next document management tool, but rather the context layer of a company. That means: we specifically capture knowledge that isn’t written down anywhere – empirical values, routines, customer relationships, decision-making backgrounds. Through AI and voice-to-voice technology, this happens at a low barrier and almost incidentally in everyday work. Previous knowledge management has often failed because it was built past people and was far too complicated to maintain. We turn that around: we adapt to the way people work, not the other way around.
Experiences from company handovers informed the founding
Munich Startup: What triggered the founding?
Oliver Diekmann: I’ve built companies, handed them over, and built them again. With every handover, I experienced how much knowledge suddenly goes missing when the people who carried it leave. That wasn’t primarily technical knowledge, but rather context. Why decisions were made the way they were, which customer relationships really matter, the subtleties that count in everyday work. Then, as an investor, I saw how often company takeovers fail precisely at this point, and it became clear: a solution is needed here. The breakthrough in AI determined the timing. For the first time, we can really solve what was previously not scalable.
Munich Startup: Was there ever a moment when you thought about giving up?
Oliver Diekmann: No. On the contrary, the feedback from many mid-market companies that they need our solution, and seeing the huge potential, reinforces our commitment. A little humility doesn’t hurt, though. Success doesn’t come overnight, but only through the steady hard work of a good team. And it certainly helps that Wingmaite isn’t my first founding. That makes you a bit more resilient and calmer.
Wingmaite was founded in 2025 and is developing an AI-based solution to secure and make implicit experiential knowledge usable in companies. Behind Wingmaite are Oliver Diekmann, Co-Founder and CEO, and Christian Zacharias, Co-Founder and CTO. Diekmann is a serial entrepreneur and angel investor with over 15 years of experience in the mid-market and private equity sector.
Munich Startup: How would you know in a year that you’re on the right path?
Oliver Diekmann: By companies working with us saying after six months: “We should have done this three years ago.” Concretely, that means over 50 percent of our users say they don’t want to do without Wingmaite. Customers who onboard measurably faster, structure successions more cleanly, and build AI agents based on their secured knowledge that create real added value. And: the topic of corporate dementia has arrived in public debate and is being taken seriously.
“Munich is our anchor, but not our limit”
Munich Startup: Would you found again in Munich and why?
Oliver Diekmann: In a heartbeat. Munich has a strong tech ecosystem and at the same time proximity to the industrial mid-market in southern Germany – the companies we’re building for. The city attracts top talent, has a vibrant startup scene, and offers credibility as a location when you’re talking to mid-market business owners and investors. At the same time, we work fully remote with a team spread across Germany and Portugal. Munich is our anchor, but far from our limit.
Munich Startup: Bootstrapping or venture capital?
Oliver Diekmann: We are essentially bootstrapped and funded to a smaller extent by business angels, but we’ll also close a funding round this year. Building knowledge infrastructure for the mid-market requires speed and investment. At the same time, we make sure our business model is based on genuine customer value from the start. The right balance between bootstrapping mentality and the momentum that external capital provides is key for us.
