# 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.

- **Founded:** 2020
- **Headquarters:** Chicago, United States
- **Founders:** Jan Seale (Co-Founder & CEO), Coabi Kastan (Co-Founder & COO)
- **Team size:** Approx. 84 (per company data); reported as a small team
- **Products:** OOO Mobile App, AI Trip Generator, Social Recommendation Feed, In-App Booking
- **Notable:** Raised roughly $5M across pre-seed and seed rounds while launching during the COVID-19 pandemic., Co-founder Jan Seale is among the first 100 Black women to raise over $1M in venture capital., Grew coverage to 3,500+ cities with a trusted-recommendation model.

## Products & services

- **OOO Mobile App** — iOS and Android app to browse curated places, build and share itineraries, book hotels, and reserve restaurant tables using recommendations from friends and followed influencers.
- **AI Trip Generator** — A web and in-app tool that generates full trip plans from a traveler's preferences, grounded in OOO's network of trusted recommendations.
- **Social Recommendation Feed** — Follow friends and influencers to see the spots they vouch for across 3,500+ cities, rather than anonymous star ratings.
- **In-App Booking** — Hotel booking and OpenTable-powered restaurant reservations handled inside the app, with plans for direct flight booking.

## Achievements

- Raised roughly $5M across pre-seed and seed rounds while launching during the COVID-19 pandemic.
- Co-founder Jan Seale is among the first 100 Black women to raise over $1M in venture capital.
- Grew coverage to 3,500+ cities with a trusted-recommendation model.
- Launched an AI trip generator on web and app, extending beyond the original social recommendation product.
- Featured by Fortune, PhocusWire, Built In Chicago, and The Manual.

## Latest updates

- **2024-01** — Create & Cultivate feature detailing how the co-founders allocated their ~$5M in fundraising.
- **2024-05** — LinkedIn spotlight on founders Jan Seale and Coabi Kastan.
- **2024-01** — Reported last funding activity; company focus expands to AI trip generation.

## Links

- Website: https://takemeoutofoffice.com
- LinkedIn: http://www.linkedin.com/company/oootravel
- Instagram: https://www.instagram.com/takemeoutofoffice/
- Facebook: https://facebook.com/takemeoutofoffice

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Profile page: https://yespress.io/out-of-office
Published by YesPress — https://yespress.io
Last updated: 2026-07-03