Upside Business Travel
Upside Business Travel's Overview
Upside Business Travel was a technology company that offered a platform designed to simplify business travel booking for small and medium-sized businesses (SMBs). Founded by Priceline founder Jay Walker in 2015, Upside aimed to provide cost savings for companies while rewarding employees with gift cards for choosing more economical travel options. The platform integrated flights, hotels, and rental cars. In May 2019, Upside Business Travel was acquired by CWT (formerly Carlson Wagonlit Travel), a global leader in business travel management. Upside's technology and team were integrated into CWT to enhance its offerings for the SMB market.
Where is Upside Business Travel's Headquarters?
HQ Function
Served as the central hub for product development, engineering, sales, marketing, operations, and corporate leadership before the CWT acquisition.
Notable Features:
Located in a modern office building in the historic Georgetown area, likely offering contemporary amenities suited for a tech startup environment.
Work Culture:
As a venture-backed startup, Upside likely fostered a dynamic, fast-paced, and innovative work culture focused on disrupting the traditional corporate travel model for SMBs.
HQ Significance:
The HQ was the birthplace and operational core of Upside's unique business travel platform and incentive model, driving its growth until the acquisition.
Values Reflected in HQ: The headquarters likely embodied Upside's values of innovation, customer-centricity (targeting SMB needs), and efficiency in travel management.
Location:
Prior to its acquisition by CWT, Upside Business Travel's operations and customer base were primarily focused on the United States market, specifically targeting US-based small and medium-sized businesses.
Street Address:
1055 Thomas Jefferson St NW, Suite 600
City:
Washington
State/Province:
D.C.
Country:
USA
Upside Business Travel's Global Presence
Buying Intent Signals for Upside Business Travel
Highperformr Signals uncover buying intent and give you clear insights to target the right accounts at the right time — helping your sales, marketing, and GTM teams close more deals, faster.
Executive Team of Upside Business Travel
As of April 2025, Upside Business Travel' leadership includes:
Investors of Upside Business Travel
Upside Business Travel has been backed by several prominent investors over the years, including:
Executive New Hires/Exits in the Last 12 Months
No executive hires or exits have been reported for Upside Business Travel as an independent entity within the last 12 months. The company was acquired by CWT in May 2019, leading to the integration of its team and leadership within CWT or departures related to the acquisition.
Technology (Tech Stack) used by Upside Business Travel
Discover the tools Upside Business Travel uses. Highperformr reveals the technologies powering your target accounts — helping your sales, marketing, and GTM teams prioritize smarter and close faster.
Upside Business Travel Email Formats and Examples
Following the acquisition by CWT, original Upside Business Travel email addresses (@upside.com) are no longer actively used for company operations. Communication would typically occur through CWT channels.
[first_initial][last]@upside.com (Defunct)
Format
scase@upside.com (Example, Defunct)
Example
0%
Success rate
News and media
TechCrunch • May 28, 2019
CWT acquires Upside Travel to boost its travel booking platform for SMBs
CWT (formerly Carlson Wagonlit Travel) announced its acquisition of Upside Business Travel. The move aimed to strengthen CWT's offerings for the small and medium-sized business market by integrating Upside's technology platform and expertise....more
Skift • May 28, 2019
CWT Acquires Upside Business Travel to Accelerate Push Into Small Business Market
CWT acquired Upside Business Travel, a startup known for its SMB-focused booking tool and rewards program. The acquisition signaled CWT's increased focus on capturing a larger share of the small corporate travel market....more
Skift • April 26, 2017
Upside Raises $57 Million to Further Challenge Corporate Travel Booking
Upside secured $57 million in a mix of equity and debt financing, led by Red Ventures. The funding was intended to fuel the growth of its platform targeting underserved small business travelers....more
The Points Guy • September 19, 2016
Priceline Founder Jay Walker Launches Upside Business Travel Site
Upside officially launched its business travel platform, founded by Priceline's Jay Walker. The service aimed to help small and medium businesses save money on travel while offering gift card rewards to employees for making cost-conscious choices....more
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