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Out of Office
Out of Office (OOO) is a Chicago-based travel technology company that helps people plan trips using recommendations from the people they actually trust - friends, family, and the influencers they follow - instead of anonymous review sites. Founded in 2020 by former Trunk Club executives Jan Seale and Coabi Kastan, the app lets travelers browse curated spots across thousands of cities, build and share itineraries, book hotels, and reserve restaurant tables in one place, and more recently generate full trip plans with an AI trip generator.
Jan Seale
Jan Seale is the CEO and co-founder of Out of Office, a Chicago-based travel app that turns recommendations from your own friends and trusted circle into bookable trips across thousands of cities. A Cornell grad who spent years at Gap, Trunk Club, and Havenly before building her own company, she launched a travel startup in the middle of a global pandemic - and became one of the first 100 Black women in the United States to raise more than a million dollars in venture capital. She runs on gratitude, literally: she starts every morning by naming ten things she is grateful for.