CEO at Ambiguous
Ryan Waliany
Ryan Waliany is a serial entrepreneur and investor, currently founder and CEO of Ambiguous, where he builds AI coworkers that collaborate with humans through everyday tools like email, Slack, and Google Docs. He has a track record of scaling ventures from idea to multi-million-dollar businesses, combining operational expertise with a vision for the future of work.
Questions & Answers
What's the story behind your company?
Ambiguous was born from the realization that most back-office tasks are repetitive, low-complexity, and high-volume—yet still consume valuable human attention. We set out to create AI coworkers that work like teammates, equipped with real identities and accounts, so they can collaborate naturally alongside people in tools they already use.
What sets you apart from others in your industry?
Unlike point-solution automation or single-agent tools, Ambiguous builds AI coworkers that share the same task lists, credentials, and communication channels as humans. This makes collaboration seamless and opens the door to complex, cross-functional workflows where AI and people truly work side-by-side.
What's a memorable 'aha' moment you've had while building your startup?
One turning point came when I dropped a real customer complaint into ChatGPT—and it worked. That small experiment revealed the missing piece for scaling operations: AI could handle the high-frequency tasks that bog down teams, freeing people to focus on judgment and strategy.
