TrustLayer's Fox launches Vail insurtech retreat as fresh funding wave threatens to replay last cycle’s mistakes

Insurtech's new capital wave is producing a generation of founders without the institutional memory to avoid repeating the last cycle's most expensive mistakes, according to TrustLayer partnerships and carrier sales leader Sharon Fox, who has launched a Vail retreat to address the gap.

The 2026 Vail Insurtech Ski Retreat runs February 22 to 25 at Edwards Estates and Vail Resort, bringing together a small group of insurtech leaders, founders and investors for four days of roundtable sessions designed to foster candid operator dialogue outside the traditional conference circuit.

With funding returning to the sector, insurtech is once again drawing entrepreneurs and investors from outside the insurance industry, many of whom have not operated through prior downturns or navigated insurance’s regulatory, carrier and distribution realities.

Fox said that dynamic makes shared experience particularly valuable.

“Coming together to share war stories – learning things to avoid, things to run towards – that’s universal,” she said. “Tech can be different, but experiences are usually pretty relatable.”

She added that while large conferences provide exposure to leaders and investors, they do not always create space for more vulnerable conversations.

“Big conferences can be overwhelming, not knowing who to connect with,” Fox said. “Insurtech can be cliquey. What I want it to be is a community.”

Fox said smaller settings allow founders to move beyond public projection and discuss operational challenges more openly — a dynamic she believes is especially important for first-time entrepreneurs testing ideas in a complex industry.

“There are a lot of people out there toying with entrepreneurship and stepping out on their own,” she said. “Exposing yourself to people in the early stages of doing that is super beneficial.”

'BUILD YOUR PELOTON'

She recalled advice from an early TrustLayer investor that continues to shape her approach: build your peloton.

“One of our investors said it’s about your network, how many people you can put in your peloton,” she said. “How many people do you put in your peloton that you can come to for help and empowerment?”

The cycling metaphor reflects the retreat’s structure: small-group roundtables designed to create sustained peer networks rather than surface-level introductions.

TrustLayer is a San Francisco-based collaborative risk management platform that automates the verification of insurance, licenses and compliance documentation between businesses and their partners.

Fox said more than 3,500 people have viewed the event page to date, underscoring what she described as strong interest in smaller-format industry gatherings.

Fox said she is also organizing a separate women-focused insurtech gathering scheduled for September 26 to 28 in Phoenix, timed to coincide with InsureTech Connect.

She said the event will aim to create a dedicated forum for women operating in the insurtech ecosystem.