Squaremouth
Squaremouth is a privately held online travel insurance comparison marketplace that aggregates 20+ carriers and 100+ plans, enabling individual travelers to quote, compare, and purchase policies directly via its website and phone support, with Tin Leg as an owned sub-brand.
- Company typePrivate
- Founded2003
- HeadquartersFort Wayne, United States
- Headcount11–50
- GTM typeB2C
- OfferingDigital Commerce or Content
What Squaremouth does
Squaremouth is a St. Petersburg, Florida-based online travel insurance comparison marketplace founded in 2003 and operated as a division of Specialty Program Group LLC. The platform aggregates 20+ top-rated U.S. travel insurance carriers and 100+ plan types, enabling individual travelers to quote, compare side-by-side, and purchase policies in a single self-serve workflow across categories including comprehensive single-trip, annual/multi-trip, cruise, adventure and sports, flight, group, medical, international, and family coverage. Squaremouth also owns Tin Leg, a proprietary sub-brand selling travel insurance directly through the same platform, providing an additional captive supply channel alongside third-party carriers.
The core technology is a comparison marketplace with real-time quote generation, side-by-side plan filtering, and integrated purchase flow, supplemented by the proprietary Zero Complaint Guarantee claims advocacy service. Distribution is exclusively direct-to-consumer via squaremouth.com and a 1-800 phone sales line staffed 8AM-10PM ET daily; there is no field sales, channel partner, or retail footprint. Marketing is content- and SEO-led, anchored by proprietary Travel Insurance Trends Reports that generate recurring earned media in The New York Times, CNN, USA Today, The Wall Street Journal, and Bloomberg.
Squaremouth generates revenue primarily through carrier commissions on policies sold through the marketplace, augmented by direct revenue from Tin Leg-branded policies sold on its own platform. Over 4.6M travelers have used the platform historically, and the company is privately held with no external venture funding, having grown organically under Specialty Program Group's ownership.
Squaremouth firmographics
Firmographics- Name
- Squaremouth
- Legal name
- Squaremouth LLC
- Website
- https://squaremouth.com
- Company type
- Private
- Founded year
- 2003
- Operating status
- Operating
- Headcount range
- 11–50 employees
- Short description
- Squaremouth is a privately held online travel insurance comparison marketplace that aggregates 20+ carriers and 100+ plans, enabling individual travelers to quote, compare, and purchase policies directly via its website and phone support, with Tin Leg as an owned sub-brand.
- Ownership category
- akta.pro rank
Squaremouth industry classification
Industry- Product category
- Travel Insurance Comparison / Travel Insurance Marketplace
- NAICS
- Insurance Agencies and Brokerages (524210)
- SIC
- Fire, Marine & Casualty Insurance (6331)
- akta.pro primary industry
- Compliance, Regulatory Reporting & Insurance Document Automation (THALALAL)
- akta.pro secondary industry
- Travel Supplier Protection & Liability (Airline/Hotel/Tour Operator) Platforms (THALALAJ)
Keywords
Where Squaremouth is headquartered
LocationHeadquarters
- HQ city
- Fort Wayne
- HQ country
- United States
- HQ region
- North America
Offices1 record
Markets served
Squaremouth business model
Business model- GTM type
- B2C
- Offering type
- Digital Commerce or Content
- Cost components
- Personnel, Technology or R&D, Marketing or Sales, Operations, Infrastructure
Revenue model
- Insurance Provider Commissions: Squaremouth earns commissions from insurance providers when customers purchase policies through their marketplace platform. This is the primary revenue stream for the comparison site.
- Tin Leg Brand: Tin Leg is a Squaremouth brand that offers travel insurance products directly. Revenue from Tin Leg sales flows through Squaremouth's own insurance subsidiary.
Pricing tiers
| Model | Billing | Price |
|---|---|---|
| Subscription | Pay-as-you-go | Comprehensive Travel Insurance - Standard single trip coverage for occasional travelers |
| Subscription | Annual | Annual/Multi-Trip Plans - Cost-effective coverage for frequent travelers |
| Usage-based | Pay-as-you-go | Travel Medical Insurance - Medical coverage for travelers abroad |
| Subscription | Pay-as-you-go | Cancel For Any Reason (CFAR) Add-on Coverage |
Go-to-market motion2 records
Distribution channels3 records
Marketing channels5 records
Squaremouth product offering
Product offeringCore offering
Squaremouth operates an online travel insurance comparison marketplace that aggregates quotes from more than 20 top-rated U.S. insurance providers across 100+ plans, allowing travelers to enter trip details, compare coverage side-by-side by benefits and price, and purchase a policy online or via phone. The company earns commissions from insurance carriers on policies sold through the platform and also sells travel insurance directly through its wholly-owned Tin Leg brand, supported by a claims advocacy service called the Zero Complaint Guarantee.
Product overview
Squaremouth operates as America's largest travel insurance comparison marketplace, offering a platform that aggregates and compares travel insurance policies from over 20 top-rated insurance providers. The core platform enables travelers to quote, compare, and purchase travel insurance through multiple plan types: Comprehensive Single Trip Plans, Annual/Multi-Trip Plans, Group Plans, Cruise Insurance Plans, Adventure & Sports Plans, Flight Insurance Plans, Travel Medical Plans, International Travel Insurance, and Family Travel Insurance. The company also owns the Tin Leg sub-brand, which offers proprietary products recognized by U.S. News & World Report. Key product features include optional Cancel For Any Reason (CFAR) and Interruption For Any Reason (IFAR) add-ons available across many plans, along with a proprietary Zero Complaint Guarantee claims advocacy service. The company publishes Travel Insurance Trends Reports and a Hurricane Travel Insurance Guide as customer education resources. Insurance providers on the platform include Tin Leg (Squaremouth brand), IMG, Travel Insured International, Seven Corners, WorldTrips, Generali Global Assistance, Berkshire Hathaway Travel Protection, Travelex, BlueCross BlueShield Global Solutions, Aegis, Trawick International, HTH Travel Insurance, Detour Insurance, John Hancock Insurance Agency, battleface, Arch RoamRight, SafeTrip by UnitedHealthcare Global, MedjetAssist, USI Affinity, and AXA Assistance USA.
Differentiator
Problem solved
Functional benefit
Brands
- Tin Leg: A Squaremouth brand recognized by U.S. News & World Report as Best Travel Insurance Company of 2026, ranking first in Most Affordable Travel Insurance Companies and Best Cruise Insurance Companies.
Products and services
- Comprehensive Travel Insurance (Single Trip Plans) Standard single-trip travel insurance plans for occasional international or domestic travelers seeking essential coverage for one specific trip, including trip cancellation, medical emergencies, delays, baggage loss, and emergency evacuation. Sold via Squaremouth's comparison marketplace.
- Annual Travel Insurance Cost-effective annual or multi-trip travel insurance policies providing emergency medical, medical evacuation, and travel delay coverage for multiple trips over a 12-month period, designed for frequent travelers.
- Group Travel Insurance Travel insurance for groups of 10 or more travelers heading to the same destination, offering comprehensive coverage benefits across the entire party traveling together.
- Cruise Insurance Plans Travel insurance policies specifically designed for cruise travelers, covering missed ports, shipboard medical emergencies, itinerary changes due to weather or mechanical issues, and emergency evacuation.
- Adventure & Sports Travel Insurance Specialized travel insurance for thrill-seekers that covers high-risk activities such as skydiving, bungee jumping, mountain climbing, scuba diving, and skiing, including sports equipment protection and activity fees.
- Flight Insurance Plans Travel insurance covering flight cancellations, flight changes, airline delays, missed connections, weather disruptions, meal and hotel expenses during delays, and lost luggage.
- Travel Medical Insurance Medical-only travel insurance for travelers going abroad, providing coverage for what their regular domestic health insurance does not cover while overseas.
- International Travel Insurance Comprehensive travel insurance tailored for international trips, featuring high medical evacuation limits and benefits specific to overseas travel risks.
- Family Travel Insurance Travel insurance designed for families traveling together, with benefits structured to protect family trip investments and address family-specific travel risks such as dependent medical coverage.
- Tin Leg Travel Insurance (Squaremouth Brand) Tin Leg is a Squaremouth-owned travel insurance brand offering affordable travel insurance products directly through the Squaremouth platform, ranked by U.S. News & World Report in 2026 as Most Affordable Travel Insurance Company and Best Cruise Insurance Company.
Quantifiable outcome
- Travelers can save money by comparing policies to find the most affordable option
- +2 more outcomes
Companies that use Squaremouth
Customer profileNamed customers5 records
Segments6 records
Ideal customer profiles6 records
Squaremouth technology and API
TechnologyTechnology focussed Yes
API detail
- Has API
- No
- API docs
- API detail
Core technology
AI maturity
App detail
AI capability1 record
Feature3 records
Squaremouth partnerships and signals
Strategic signalPartnerships
Two partnerships are on record, tiered core.
- Tin LegcoreTin Leg is a Squaremouth-owned brand offering travel insurance products. As a wholly-owned brand, Tin Leg operates as part of Squaremouth's product portfolio, allowing the company to offer proprietary insurance products alongside third-party providers on the platform.
- Insurance Providers (20+)coreSquaremouth aggregates 20+ top-rated travel insurance providers on its platform including Tin Leg, IMG, Travel Insured, Seven Corners, WorldTrips, Generali, Berkshire Hathaway, Travelex, BCBS Global Solutions, Aegis, Trawick International, HTH Travel Insurance, Detour Insurance, John Hancock, battleface, Arch RoamRight, SafeTrip, MedjetAssist, USI Affinity, and AXA Assistance. These providers integrate with Squaremouth's comparison platform to offer their products.
Scale indicators11 records
Recent moves5 records
Expansion highlights5 records
Squaremouth competitors and assessment
Company assessmentDirect peers
- AARDY: Travel insurance comparison site that aggregates carrier plans with a focus on competitive pricing and educational content, targeting the same consumer insurance buyer as Squaremouth.
- TravelInsurance.com: Online travel insurance comparison platform that aggregates multiple providers and offers quote/comparison/purchase flows, serving the same consumer shopping behavior as Squaremouth.
- InsureMyTrip: Direct competitor operating a travel insurance comparison marketplace aggregating multiple carriers with side-by-side quoting and customer reviews, structurally identical to Squaremouth's model.
- TripInsuranceStore.com: Boutique travel insurance comparison marketplace aggregating multiple carriers, serving travelers seeking side-by-side plan comparisons similar to Squaremouth.
Emerging players
- Faye: Modern, app-based travel insurance startup with bundled coverage and claims via a digital wallet; competing for the same consumer insurance dollar as Squaremouth with a different UX paradigm.
- SafetyWing: Digital-first travel medical insurer targeting remote workers and digital nomads with a subscription model; represents the next-gen, mobile-first competitive threat Squaremouth faces in younger segments.
Broad incumbents
- World Nomads: Established travel insurance brand targeting adventure and long-tail international travelers; competes directly for the same trip-cancellation and medical-evacuation buyers Squaremouth serves.
- Berkshire Hathaway Travel Protection: Major travel insurance carrier backed by Berkshire Hathaway's specialty insurer; a Squaremouth-listed provider that also sells direct, embodying the carrier vs. aggregator dynamic.
- Travelex Insurance Services: Large US travel insurance provider and Squaremouth-listed partner; sells plans direct and through aggregators, representing the carrier side of the comparison model Squaremouth aggregates.
- Allianz Travel Insurance: One of the largest global travel insurance carriers and a Squaremouth-listed provider, offering plans direct to consumers and through partners; competes as a single carrier inside Squaremouth's marketplace.
Market position
Strengths5 records
Weaknesses5 records
Competitive moat5 records
Key risks6 records
Key highlights6 records
Customer concentration
Squaremouth social profiles
Digital presenceSquaremouth financial estimates
Financial estimateRevenue estimate
Valuation estimate
Squaremouth leadership team
Management profileNumber of profiles
Profiles5 records
Squaremouth subsidiaries and ownership
Company hierarchySubsidiaries1 record
Squaremouth funding detail
Funding detailFunding overview
Funding rounds
Investors
Funding detail is available on the Subscription and Enterprise plan.Contact sales →
Squaremouth M&A and investment
M&A and investmentM&A
Investments
M&A and investment is available on the Subscription and Enterprise plan.Contact sales →
Frequently asked questions about Squaremouth
What does Squaremouth do?
Squaremouth operates an online travel insurance comparison marketplace that aggregates quotes from more than 20 top-rated U.S. insurance providers across 100+ plans, allowing travelers to enter trip details, compare coverage side-by-side by benefits and price, and purchase a policy online or via phone. The company earns commissions from insurance carriers on policies sold through the platform and also sells travel insurance directly through its wholly-owned Tin Leg brand, supported by a claims advocacy service called the Zero Complaint Guarantee.
Is Squaremouth a public or private company?
Squaremouth is a private company. It is classified as corporate owned and is currently operating.
When was Squaremouth founded?
Squaremouth was founded in 2003. It employs 11 to 50 people.
Where is Squaremouth based?
Squaremouth is headquartered in Fort Wayne, United States, in the North America region.
How does Squaremouth make money?
Two revenue lines are on record. Insurance Provider Commissions are the primary driver. The others are tin Leg Brand.
Who are Squaremouth's main competitors?
Direct peers on record are AARDY, TravelInsurance.com, InsureMyTrip and TripInsuranceStore.com. Emerging players are Faye and SafetyWing. Broad incumbents are World Nomads, Berkshire Hathaway Travel Protection, Travelex Insurance Services and Allianz Travel Insurance.
Does Squaremouth have an API?
No public API is recorded for Squaremouth.
What industry is Squaremouth in?
Squaremouth's product category is Travel Insurance Comparison / Travel Insurance Marketplace. Its primary akta.pro industry code is THALALAL, Compliance, Regulatory Reporting & Insurance Document Automation, with a secondary code of THALALAJ, Travel Supplier Protection & Liability (Airline/Hotel/Tour Operator) Platforms. Its NAICS code is 524210 and its SIC code is 6331.