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Sidestep

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Travel search engine that generates revenue via advertising and referral fees

United StatesFounded 1999Travel
Valuation $100–500M Latest valuation · 2007
Headcount <100 Current team size
Total funding $10–50M Disclosed equity funding
Unlock exact values This page shows ranges. Dealroom has the exact numbers for Sidestep and the history behind them.

About Sidestep

Sidestep.com operates as a travel search engine that helps users find and compare flights, hotels, and car rentals. The platform serves budget-conscious travelers looking for the best deals on travel-related services. Sidestep.com aggregates data from various travel providers, allowing users to compare prices and options in one place. The company operates in the online travel market, which is highly competitive and includes major players like Expedia and Kayak. Sidestep.com generates revenue through affiliate marketing and advertising, earning commissions when users book travel services through their platform. The business model focuses on providing a user-friendly interface and comprehensive search tools to attract and retain users.

Source: Dealroom company data

At a glance

Status
Acquired
Founded
1999
Headquarters
United States
Employees
30
Open positions
None listed
Dealroom signal
83.4/100
Industry
Travel
Sub-industry
Booking & Search
Sector
Navigation, Adtech, Advertising, Travel, Search Engine, Mapping, Camping
Client focus
b2c
Investment activity
1 company, latest Nov 2006
Capital deployed
Preferred round
ACQUISITION

Latest news

Press, funding announcements and product moves mentioning Sidestep.

See all news

Funding history

6 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
ACQUISITIONExit Aug 2019 $0 Undisclosed
ACQUISITIONExit Dec 2007 $200M $200M Kayak
Showing the latest 2 of 6 recorded eventsBook a demo for the full funding history →

Growth signals

Sidestep website traffic

Latest recorded traffic for Sidestep is 240 monthly website visits, down 42.9% over the last three months. Sidestep's team grew 76.5% over the past year.

Latest monthly visits240 3-month web change-42.9% 1-year team growth+76.5%
Summary metrics are public; monthly history is available with a demoCompare with peers →

Similar companies

Closest operating peers by Dealroom taxonomy

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Showing 8 of the closest matchesCompare every metric →

Investments and acquisitions

Capital deployed

Recent portfolio relationships for companies that also act as investors or acquirers.

Investors

8 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Series A2 investors entered at this stage

  • Lehman Brothers
  • Trident Capital

Series B and later3 investors entered at this stage

Other known investors3 additional known investors

Team profiled 19 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 1 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
1 countries with
team presence
🇿🇦 South Africa100%
1 country shown

Market sentiment

Posts on X, past 7 days

An AI-synthesised read of the highest-engagement posts about Sidestep on X, ranked by likes and reposts, corporate channels excluded.

Reading the room on X — pulling top posts and synthesizing themes…

Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour

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