Anna Sun is co-founder and CEO of Nowadays, the first AI platform for corporate events. She started the company with her sister Amy in 2023 out of Y Combinator, after both of them spent years watching companies pour time and money into a process nobody had bothered to fix.
Anna studied Computer Science at MIT, where she served as Class President and managed a $500K budget for events serving 1,300+ students. She watched her team overpay for basic ballroom space simply because they never had the time to negotiate. Amy, then at Google, was seeing the same thing at a far larger scale.
Nowadays automates the work that has kept corporate event planning stuck in email threads and spreadsheets for two decades. Its AI sources venues, sends RFPs, calls and emails hotels in 22+ languages, and negotiates rates across a database of 400,000+ venues worldwide. The company has grown to $20M in booked revenue from over 250 clients including Google, Airbnb, and BlackRock, and has handled events like a 475-person gathering at Universal Studios and a hotel buyout in Thailand featured in White Lotus season 3.
Previously a software engineer at Datadog, DoorDash, and Amazon, Anna recently completed a 70.3 Ironman in Santa Cruz!
Industry: AI for corporate travel and events. Specifically: applying AI agents to enterprise meetings and events spend, a category still run almost entirely on email, phone calls, and spreadsheets. More broadly, vertical AI for operations-heavy industries that legacy software promised to fix twenty years ago and never did.
Why I’m excited to be part of WIN Awards: Nowadays is two sisters and a majority female team, building in an industry that has not seen real innovation in twenty years. Most of the rooms we walk into do not look like us. Being recognized alongside this group is a reminder that we are not the exception, and that there is a whole network of women doing the same thing in their own industries. Mostly I am excited about the people. The WIN community is full of women who are actually shipping, and those are the peers I learn the most from.
