This week’s tech mafia Monday piece spotlights Kayak.com, one of the Boston area’s flagship web 2.0 companies in the last decade. Kayak.com is a travel search engine that aggregates information from hundreds of travel and reservation sites across the web, allowing consumers to compare travel options more easily.
Kayak’s story underscores the power of a founding team of allstarss with prior experience in the same industry joining forces. Three of Kayak’s founding team members were previous founders of what was then known as travel’s “Big Three” – Orbitz, Travelocity and Expedia. What’s more, it has been nearly 7 years since the company was formed in January 2004, and that founding team still appears to be materially involved in the company.
After amassing a strong founding team (including the co-founder of General Catalyst Partners which helped infuse early capital) and architects to build their core technology, in November 2004 Kayak landed strategic investment from AOL. A month later they closed a $7 million Series B round led by California-based Sequoia Capital. While founded in Norwalk, Conn., this capital helped Kayak launch in beta in early 2005 with a staff of 26 in Concord, Mass. They posted $3MM in revenue later that year.
Kayak continued to grow and forge partnerships in 2006, landing a $11.5 million Series C round led by Accel Partners in May of that year for further expansion and marketing. And with competition in the space heating up, Kayak went on to raise $196 million in December 2007 to purchase California-based competitor SideStep.com, skyrocketing Kayak to being the fifth-largest travel brand on the web.
Today, Kayak is the largest web 2.0 travel site in the world and a global Internet media company, operating Kayak.com, Sidestep.com, TravelSearch.com, and TravelPost.com. Kayak’s “Search one and done” tagline is embodied in their newest ad campaign:
Joel Cutler
Prior to: Managing Director and Co-Founder of General Catalyst Partners
At Kayak: Co-founder
Now: Cutler is still with General Catalyst, currently serving on the board of FanSnap, ITA Software, TravelPost, and Roost.
Paul English
Prior to Kayak: Founder of gethuman.com
At Kayak: Co-founder and CTO
Now: English continues to serve as CTO of Kayak, and has been an adviser to LinkedIn and FanSnap for the last 3 years.
Steve Hafner
Prior to: Co-founder and EVP, Consumer Travel at Orbitz
At Kayak: Co-founder and CEO
Now: Hafner continues to serve as CEO of Kayak
Terrell Jones
Prior to: Founder and CEO of Travelocity.com
At Kayak: Chairman of the Board
Now: Jones remains Chairman of the Board at Kayak and is Principal of his consultancy, Essential Ideas
Greg Slyngstad
Prior to: Founder and Executive VP at Expedia.com
At Kayak: Founder and Board Director
Now: Slyngstad serves as Board Director at Roost and Kayak, and also serves as CEO of TravelPost
