SmarterTravel

SmarterTravel

AI-driven online travel planning and booking

Overview

SmarterTravel is a data-driven travel tech company that uses AI and machine learning to power a consumer-focused online travel experience. It combines broad flight and hotel content with personalized recommendations so travelers can search, compare, and book trips quickly and confidently. The company operates a family of sites—Smartertravel.com, airfarewatchdog.com, oyster.com, familyvacationcritic.com, and bookingbuddy.com—each providing flight, hotel, and destination content and tools. Its goal is to become the destination travelers return to for planning and booking trips by offering a seamless mix of breadth and trusted recommendations.

About SmarterTravel

Simplify's Rating
Why SmarterTravel is rated
C
Rated C on Competitive Edge
Rated C on Growth Potential
Rated C on Differentiation

Industries

Consumer Software

Entertainment

Company Size

11-50

Company Stage

Series B

Total Funding

$9.5M

Headquarters

Boston, Massachusetts

Founded

1998

Get referred to SmarterTravel

See people who can refer or advise you

Simplify Jobs

Simplify's Take

What believers are saying

  • SmarterTravel.com and related brands were actively updated through September 2026.
  • Its latest articles cover fees, passenger rights, and hotel guarantees, sustaining search demand.
  • Personalized travel content fits consumers seeking cheaper bookings during volatile airline pricing.

What critics are saying

  • Cordova v. Smarter Travel Media LLC entered California court in March 2026.
  • Tripadvisor sold SmarterTravel after a 2020 restructuring that eliminated nearly 900 jobs.
  • Travel content faces Google and OTA pressure, squeezing traffic and advertising margins quickly.

What makes SmarterTravel unique

  • SmarterTravel owns eight legacy travel brands, including SmarterTravel, Oyster, and Airfarewatchdog.
  • Its AI-driven recommendation engine targets consumers with personalized travel content and acquisition funnels.
  • The 2021 Link Ventures and Second Alpha financing backed its data-science-led travel media model.

Help us improve and share your feedback! Did you find this helpful?

Funding

Total Funding

$9.5M

Above

Industry Average

Funded Over

0 Rounds

Benefits

Medical, dental, vision & life insurance benefits

Paid parental leave

Family leave

Generous PTO

Flexible workday

401k

Fsa account

Health & entertainment subscriptions

Growth & Insights and Company News

Headcount

6 month growth

↑ 0%

1 year growth

↑ 0%

2 year growth

↑ 0%
TechCrunch
Sep 15th, 2021
SmarterTravel sheds HopJump name, begins a new journey with $9.5M round

Travel startups continue to rake in venture capital dollars as more people become comfortable traveling amid the global pandemic. The latest is SmarterTravel, which brought in $9.5 million in Series B funding co-led by Link Ventures and Second Alpha, with existing investors also participating.

Recently Posted Jobs

Sign up to get curated job recommendations

There are no jobs for SmarterTravel right now.

Find jobs on Simplify and start your career today

We update SmarterTravel's jobs every few hours, so check again soon! Browse all jobs →