May 5, 2026

SkiSync Increases Trip Protection Conversion 300% with Built-In Coverage

SkiSync and Outside Life needed automated, flexible insurance options for their platform users. Within six months of partnering with Vertical Insure, they exceeded policy sales for the full previous year.
Image of skiers on a ski lift with Outside Life and SkiSync logos

Trip Protection conversion rates are up

%

over previous carrier

Surpassed previous annual premium in the first

months

“We were thrilled to switch from manual spreadsheets and hand trip protection off to a provider we know will take care of our platform and our customers, and we were excited about the opportunity to offer refund protection for season pass purchasers.”

Chris Aragon

Director of Operations, SkiSync

“Another key benefit is having clear visibility into our platform’s policy sales and conversion rates right within the partner portal. We’ve had the opportunity to A/B test features with Vertical Insure which has given us crucial insights that have helped us go after continuous growth.”

Chris Aragon

Director of Operations, SkiSync

SkiSync and Outside Life help skiers plan group ski trips at dream destinations around the world. Born from a friend group’s trip to Big Bear, California, the platform was created by skiers for skiers. With SkiSync, ski groups can create personalized, curated experiences, booking their travel, lodging, lift tickets, equipment rentals, and more, all in one place. SkiSync’s sister platform, Outside Life, provides a similar experience, tailored to college students and recent grads, offering simplified group trip planning that helps young adults create impactful experiences and lasting memories.
Now, SkiSync / Outside Life offer Trip Protection that’s embedded right into their platform through Vertical Insure. Customers can also opt in for Refund Protection when they purchase season passes through SkiSync / Outside Life. Insuring your trip through SkiSync / Outside Life wasn’t always as easy for the end user as clicking a button. Needing simplified yet tailored solutions their previous carrier didn’t provide, the platform connected with Vertical Insure.

The Challenge: Heavy Administrative Burden and Inflexible Coverage Options

Those booking ski trips love adventure, but need peace of mind. Prior to partnering with Vertical Insure, SkiSync / Outside Life offered travel insurance, but the system their previous carrier used was manual and inflexible. The platforms could only provide static, flat-rate travel insurance offerings that were not customizable to different groups’ needs. They also lacked the capability to offer refund protection to those purchasing season passes. Additionally, the platforms had to send spreadsheets to their insurance carrier every month in order to enroll their customers in travel insurance. Tired of the heavy administrative burden, SkiSync / Outside Life needed coverage that was both hands-free and customizable for the end user. They needed a provider that could embed directly into their workflow.

The Solution: Seamlessly Embedded Trip Protection and Refund Protection

Vertical Insure partnered with SkiSync / Outside Life to embed flexible insurance products directly into their platform experience. End users can now purchase:
  • Trip Protection for group ski trips
  • Refund Protection for season pass purchases
Through partnership with the Vertical Insure team, the platforms were able to quickly and efficiently implement their new protection products before peak season to provide maximum benefit for both the platforms and the end users.

The Result: Zero Administrative Burden and Hands-Free Growth

Now, trip protection is embedded directly into the end user’s shopping journey: They can plan group trips with SkiSync / Outside Life seamlessly, then add travel insurance to protect their trip. Additionally, skiers can now opt for refund protection when purchasing season passes, a feature that wasn’t available to the platforms with their previous carrier. SkiSync / Outside Life started to see the value of embedded protection right away, with over 100 policies sold within the first five days. Although the platforms experience a peak season in the fall, they have not seen a decrease in conversion rates during their off season.

Benefits for Skiers:

  • Creates peace of mind when planning trips with multiple variables
  • Provides protection when trip logistics become complex
  • Ensures refunds in the event season passes can’t be used for covered reasons

Benefits for SkiSync / Outside Life:

  • Hands-free policy sales (especially important during peak season)
  • Clear insights into policy sales and conversion rates
  • Growing insurance program that doesn’t require continual technology updates
  • Increased conversion rates

Why Vertical Insure and SkiSync / Outside Life work well together:

  • We offer a high level of customization
  • We create a simple, streamlined user experience
  • We have a passion for protecting experiences
SkiSync and Vertical Insure just make sense together: we’re both focused on providing easy-to-use software that creates a supportive, customizable experience for the end user.

Ready to upgrade your booking platform from inflexible coverage processes?

Learn more about embedding protection seamlessly into your workflow.