TripInsurance.com

What TripInsurance.com does

TripInsurance.com is a privately-held online travel insurance agency founded in 2010-2011 by Dan Skilken and operated under the legal entity Online Trip Insurance Services, Inc., a California corporation headquartered in Monte Sereno, California. The company runs a self-serve web platform that lets travelers input trip details, compare multiple travel insurance plans, and purchase coverage directly online, with policies delivered by email. TripInsurance.com is licensed as an insurance agency in all 50 US states plus DC, which constitutes the core regulatory footprint. Its product portfolio comprises Trip Insurance (a comprehensive plan for US Citizens and Residents covering cancellation, interruption, delay, missed connections, medical, evacuation, and lost luggage), Travel Medical Insurance (extendable coverage available to all travelers including international visitors and Schengen visa holders), and add-on Cruise Insurance and Flight Insurance lines.

The platform's technical foundation is described as a standard e-commerce stack with secure server infrastructure; key product components include a multi-traveler quote form (up to ten travelers) with state-of-service and citizenship selection, a comparison interface, and email-based policy delivery. There are no APIs, SDKs, or proprietary AI/ML capabilities disclosed. The differentiation narrative centers on exclusive distribution agreements with carrier partners — American Modern, BCS, Nationwide, Old Republic, and U.S. Fire — that the company says bypass traditional broker middlemen, enabling it to sell comparable coverage at roughly 40% lower prices and to anchor a "Best Price Guarantee."

TripInsurance.com monetizes exclusively through carrier commissions on policies sold via its direct-to-consumer channel; there are no brokered or intermediated channels. Pricing follows standard industry structure (roughly 4-8% of trip cost), and the company emphasizes time-sensitive benefits available within 14 days of initial deposit, including pre-existing condition waivers and Cancel-For-Any-Reason coverage. Customer acquisition is driven primarily by organic channels — SEO-oriented content marketing through a multi-section blog (Travel Tips, Best Travel Destinations, Features) and an active social presence on YouTube, Facebook, LinkedIn, and Twitter — alongside direct website traffic. The business is bootstrapped and founder-led, with 1-10 employees and no disclosed outside investment, M&A activity, funding rounds, or leadership changes.

Name

TripInsurance.com

Legal name

Online Trip Insurance Services, Inc.

Website

https://tripinsurance.com

Company type

Private

Founded year

2010

Operating status

Operating

Headcount range

1–10 employees

Short description

TripInsurance.com is a founder-led online travel insurance agency licensed in all 50 US states, offering a self-serve platform where individual travelers compare and purchase trip, medical, cruise, and flight insurance policies from major carriers via exclusive pricing agreements.

Ownership category

akta.pro rank

Product category

Travel Insurance

NAICS

Agencies, Brokerages, and Other Insurance Related Activities (5242), Insurance Agencies and Brokerages (524210)

SIC

Insurance Agents, Brokers & Service (6411), Fire, Marine & Casualty Insurance (6331), Accident & Health Insurance (6321)

akta.pro primary industry

Travel Medical & Health Insurance Platforms (THALALAC)

akta.pro secondary industries

Travel & Accident (Non-Life) Insurance (FSAJAMAN), Travel Medical Insurance (Individual) (FSAIAEAI), Baggage & Personal Effects Insurance (FSAJAJAE), Travel Insurance & Protection Products (Cruise-Specific) (THAEAFAL)

Keywords

• Travel insurance
• Trip cancellation coverage
• Travel medical insurance
• Cruise insurance
• Flight insurance

Headquarters

HQ city

Los Gatos

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Marketing or Sales, Personnel, Technology or R&D, Operations, Infrastructure

Revenue model

1. Insurance Commission Revenue: TripInsurance.com acts as an insurance agency/agent earning commissions from insurance companies when customers purchase policies through their platform. They sell travel insurance policies from the most trusted travel insurance companies and have exclusive agreements with carriers such as American Modern, BCS, Nationwide, Old Republic, and U.S. Fire.

Pricing tiers

Go-to-market motion1 record

Distribution channels1 record

Marketing channels7 records

Core offering

TripInsurance.com is an online insurance agency that sells travel insurance policies directly to consumers through a self-serve website. It offers comprehensive trip insurance for U.S. citizens and residents, travel medical insurance for all travelers, and specialized cruise and flight insurance products, sourced from carrier partners including American Modern, BCS, Nationwide, Old Republic, and U.S. Fire. Customers enter trip details into an online quote form, compare available plans, and purchase coverage that is emailed to them immediately.

Product overview

TripInsurance.com operates as an insurance agency offering a portfolio of travel insurance products. The core offerings consist of Trip Insurance (for U.S. Citizens and Residents with comprehensive coverage including cancellation, interruption, medical, and evacuation benefits) and Travel Medical Insurance (for all travelers covering illness, injury, and emergency medical costs). Specialized coverage includes Cruise Insurance and Flight Insurance as targeted add-on products. The platform functions as a comparison and sales channel, offering plans from partnered insurance carriers including US Fire Insurance Company and Nationwide Mutual Insurance Company.

Differentiator

Problem solved

Functional benefit

Products and services

• Trip Insurance

Quantifiable outcome

• Saves customers 40% or more over comparable coverage from other suppliers
• +1 more outcomes

Segments3 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature2 records

Partnerships

Five partnerships are on record, tiered core.

• US Fire Insurance CompanycoreOthersOne of the travel insurance companies whose policies are sold through TripInsurance.com. Part of the exclusive carrier agreements negotiated by the company.
• Nationwide Mutual Insurance CompanycoreOthersMajor insurance carrier whose travel insurance products are offered through TripInsurance.com. Part of the exclusive carrier agreements that enable competitive pricing.
• American ModerncoreOthersInsurance carrier with exclusive agreement with TripInsurance.com that bypasses traditional middlemen distribution, enabling lower pricing for customers.
• BCScoreOthersInsurance carrier partner with exclusive agreement with TripInsurance.com for competitive travel insurance products.
• Old RepubliccoreOthersInsurance carrier partner providing travel insurance products through TripInsurance.com's exclusive distribution agreements.

Scale indicators1 record

Recent moves6 records

Expansion highlights5 records

Direct peers

• TravelInsurance.com: TravelInsurance.com operates an online comparison and purchase platform for travel insurance from multiple carriers, targeting U.S. and international travelers. Closely mirrors TripInsurance.com's product-led, online-only agency model.
• Seven Corners: Seven Corners underwrites and distributes travel medical and trip insurance plans directly to consumers and through agents, with strong presence in travel medical coverage. Overlaps directly with TripInsurance.com's Travel Medical and Trip Insurance product lines.
• Squaremouth: Squaremouth is an online travel insurance comparison platform that sells policies from multiple carriers with a price-match guarantee. It competes head-to-head with TripInsurance.com for the same U.S. consumer self-serve travel insurance buyer.
• GeoBlue: GeoBlue specializes in international travel medical and expatriate health insurance, including coverage required for Schengen visas. Strong overlap with TripInsurance.com's Travel Medical Insurance product, particularly for international and visa-bound travelers.
• InsureMyTrip: InsureMyTrip is a leading online travel insurance comparison marketplace, allowing consumers to compare plans from multiple carriers. It is a direct competitor to TripInsurance.com in the online travel insurance agency/aggregator category with the same self-serve distribution model.
• VisitorsCoverage: VisitorsCoverage is an online travel insurance marketplace focused on international visitors, students, and travel medical coverage. Direct competitor in the online travel medical insurance comparison and purchase experience.
• World Nomads: World Nomads is a travel insurance provider serving international and adventure travelers with online quote and purchase flows. Comparable to TripInsurance.com in serving independent travelers buying trip and medical coverage online.

Emerging players

• Faye: Faye is a venture-backed travel insurance and assistance startup offering a digital-first platform with mobile app and integrated claims support. Comparable to TripInsurance.com as a next-generation online travel insurance provider, though with significantly more capital and a newer technology stack.

Broad incumbents

• Allianz Travel Insurance: Allianz Travel is one of the largest global travel insurance underwriters and distributors, selling through its own direct-to-consumer website and through agency partners including TripInsurance.com. A broad incumbent that competes both directly (via its own site) and indirectly as a supplier to niche agencies.
• AIG Travel Guard: Travel Guard is AIG's travel insurance brand offering trip cancellation, medical, and evacuation coverage sold direct and through partners. A large incumbent with significant brand recognition competing with TripInsurance.com on both direct and aggregator channels.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

• Xx.com/tripinsurance
• YouTubeyoutube.com/user/tripinsurance
• Facebookfacebook.com/TripInsurancecom
• LinkedInlinkedin.com/company/1662493

Revenue estimate

Valuation estimate

Number of profiles

Profiles1 record

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about TripInsurance.com