Red Sky

What Red Sky does

Red Sky Travel Insurance, founded in 2008 and headquartered in Kitty Hawk, North Carolina, is a privately held provider of specialized travel insurance products for the vacation rental industry. The company markets and distributes its products exclusively through professionally managed vacation rental management companies (PMCs) and registered travel retailers across the United States and Canada. Arch Insurance Company (NAIC #11150) underwrites all Red Sky policies, and Red Sky operates as a licensed travel insurance producer (CA License #0K83872, TX License #2028151, TX License #2606473). The company does not sell direct-to-consumer through retail channels; instead, guests purchasing travel insurance through partner PMCs are the end policyholders.

The company's core technology is travel insurance policy administration and claims processing for the vacation rental vertical, delivered through a five-product portfolio of destination-specific plans: Trip Preserver (general all-destination coverage), Sun Trip Preserver (coastal destinations with hurricane protection including mandatory evacuation, uninhabitable accommodations, and road closure coverage), Mountain Trip Preserver (mountain destinations covering sickness, injury, road closures, and uninhabitability), Ski Trip Preserver (ski vacations offering up to $100,000 in rental cost reimbursement and lack-of-snow coverage), and Ski Pass Preserver (season pass reimbursement). Coverage parameters include up to $25,000 in medical expense coverage, up to $525,000 in emergency medical evacuation, $200/day (max $750) for trip delay, and up to $1,250 for baggage loss. A dedicated claims portal at trippreserverclaims.com supports post-sale policyholder service.

Red Sky employs a sales-led go-to-market motion organized regionally across Rocky Mountains, California, Pacific Northwest, and national accounts, with on-site training and high-touch support provided to PMC partner staff. Revenue is generated via commissions on insurance premiums collected through registered travel retailers on behalf of Red Sky Travel Insurance. The company serves a single primary vertical — vacation rental management companies — and has built a roster of named enterprise customers including Outer Banks Blue Realty Services, Deer Valley, Sun Realty, Newman-Dailey Resort Properties, Snowmass Hospitality, Beach Properties of HH, and Corolla Classic Vacations. Leadership is led by President Laird Sager overseeing National Accounts, with Kim Casper as Vice President.

Name

Red Sky

Legal name

Red Sky Travel Insurance

Website

https://redskyinsurance.com

Company type

Private

Founded year

2008

Operating status

Operating

Headcount range

11–50 employees

Short description

Red Sky Travel Insurance, founded in 2008, is a privately held provider of destination-specific travel insurance for the vacation rental industry, distributed exclusively through vacation rental management companies and underwritten by Arch Insurance Company across the US and Canada.

Ownership category

akta.pro rank

Product category

Travel Insurance

NAICS

All Other Travel Arrangement and Reservation Services (561599), Travel Arrangement and Reservation Services (5615)

SIC

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

akta.pro primary industry

Travel Insurance (Trip Cancellation/Interruption & Delay) (FSAJAJAA)

akta.pro secondary industry

Baggage & Personal Effects Insurance (FSAJAJAE)

Keywords

• Travel insurance
• Vacation rental insurance
• Trip protection
• Ski trip insurance
• Hurricane coverage

Headquarters

HQ city

Kitty Hawk

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2B

Offering type

Services

Cost components

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

Revenue model

1. Travel Insurance Premiums: Red Sky markets and sells travel insurance products to vacation rental management companies and their guests. Insurance premiums are collected through registered travel retailers on behalf of Red Sky Travel Insurance. The company is a licensed travel insurance producer (CA License #0K83872, TX License #2028151 & #2606473). Plans are underwritten by Arch Insurance Company (NAIC #11150).

Go-to-market motion1 record

Distribution channels2 records

Marketing channels3 records

Core offering

Red Sky markets and administers specialized travel insurance products exclusively for professionally managed vacation rental management companies and their guests. Plans cover trip cancellation, trip interruption, hurricane damage, lack of snow, emergency medical, and baggage, and are underwritten by Arch Insurance Company (NAIC #11150). A portfolio of destination-specific plans — Trip Preserver, Sun Trip Preserver, Mountain Trip Preserver, Ski Trip Preserver, and Ski Pass Preserver — is distributed through registered travel retailers across the U.S. and Canada.

Product overview

Arch Red Sky is a travel insurance provider offering a portfolio of five specialized vacation rental insurance products underwritten by Arch Insurance Company. The core Trip Preserver product provides general all-destination coverage, while four destination-specific variants address particular market needs: Sun Trip Preserver for coastal/hurricane-prone areas, Mountain Trip Preserver for mountain destinations, Ski Trip Preserver for ski vacations with snow coverage, and Ski Pass Preserver specifically for ski pass reimbursement. Plans are marketed through registered travel retailers and vacation rental management companies across the United States and Canada.

Differentiator

Problem solved

Functional benefit

Products and services

• Trip Preserver General travel insurance for all destinations covering trip cancellation and trip interruption benefits to reimburse pre-paid, non-refundable vacation rental deposits when unforeseen covered events disrupt vacation plans.
• Sun Trip Preserver
• Mountain Trip Preserver
• Ski Trip Preserver
• Ski Pass Preserver

Quantifiable outcome

• Up to $100,000 reimbursement for rental costs under Ski Trip Preserver
• +4 more outcomes

Named customers9 records

Segments2 records

Ideal customer profiles2 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Partnerships

Two partnerships are on record, tiered core and minor.

• Arch Insurance CompanycoreStrategic or Co-development Partner · 1 January 2008Arch Insurance Company (NAIC #11150) is the primary underwriter for Red Sky's travel insurance products. Since 2008, Red Sky and Arch have worked together to insure guests' vacations in hurricane-prone coastal and snow dependent ski destinations. Arch Insurance Solutions mark is used by Arch Insurance Company and owned by its parent company, Arch Capital Group (U.S.). Insurance coverages are underwritten under certain policy form series, including LTP 2013 and amendments thereto.
• StayInClubminorChannel Partner/ Reseller/ DistributorStayInClub is a partner offering access to Red Sky travel insurance products through their platform for vacation rental guests. The partnership provides US and Canadian residents access to Arch Insurance Solutions travel protection plans.

Scale indicators1 record

Recent moves6 records

Expansion highlights5 records

Direct peers

• Travelex Insurance Services: Travelex Insurance Services offers trip cancellation, interruption, and emergency medical coverage through travel agents, tour operators, and supplier partnerships. Comparable to Red Sky as a US-licensed travel insurance producer distributing through travel retailers.
• Travel Insured International: Travel Insured International (a Crum & Forster company) offers US travel insurance products distributed through travel agents, tour operators, and online channels — directly comparable to Red Sky's registered-travel-retailer distribution and trip cancellation focus.
• International Medical Group (IMG): IMG sells travel medical and trip protection insurance globally through agents and online channels, including plans with trip cancellation/interruption benefits. Comparable to Red Sky as a licensed travel insurance producer with specialty coverage distributed via third-party channels.
• World Nomads: World Nomads provides travel insurance targeted at independent and adventure travelers, distributed through online and partner channels. Comparable to Red Sky as a specialty travel insurer with destination- and traveler-type-specific products, though focused on international/adventure versus US vacation rentals.
• Trawick International: Trawick International markets travel insurance plans (trip cancellation, medical, cancel-for-any-reason) through travel agents and online channels. Comparable to Red Sky's product suite and registered-travel-retailer model targeting the same vacation-traveling consumer base.
• Generali Global Assistance (Travel Insurance): Generali Global Assistance (which acquired CSA Travel Protection) is one of the largest US travel insurance providers offering trip cancellation, interruption, and emergency medical coverage through travel suppliers and online channels — directly comparable to Red Sky's core product set and distribution model via registered retailers.
• Seven Corners: Seven Corners sells travel medical and trip protection insurance through travel agents and online channels, including plans tailored to specific traveler segments. Comparable to Red Sky as a mid-sized US-licensed travel insurance producer with specialty products and reseller distribution.

Broad incumbents

• Allianz Travel Insurance: Allianz Partners is the dominant broad-market travel insurance carrier in the US, selling trip cancellation/interruption and medical products across consumer and supplier channels. Comparable to Red Sky as a competing travel insurance provider but operates at vastly larger scale and broader scope.
• Berkshire Hathaway Travel Protection: Berkshire Hathaway Travel Protection underwrites and distributes trip cancellation, interruption, and medical travel insurance through travel suppliers and direct channels. Comparable to Red Sky's product family and supplier-based distribution but operates under a much larger parent balance sheet.

Others

• Arch Insurance Company: Arch Insurance Company is the underwriting carrier for Red Sky's entire product portfolio and Arch Capital Group's US operations include arch insurance solutions travel protection. Comparable as the capital and regulatory backbone behind Red Sky's product issuance rather than as a distribution competitor.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights6 records

Customer concentration

Revenue estimate

Valuation estimate

Number of profiles

Profiles5 records

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 Red Sky