Safety Wing

Sondra Rashi had a unique vantage point on a global problem. As co-founder of SuperSide (a freelance designer platform) and with a background in economics, computer science, and policy work for the Norwegian government, he noticed something critical: the internet labor market was fundamentally global, but all the infrastructure supporting it—social safety nets, benefits, insurance—was designed locally. "If you're hiring a freelancer from Guatemala, they will not qualify for your social safety net," he observed. The insight was clear: this infrastructure needed to be rebuilt for the digital age.

In 2016-2017, Sondra set out to create a modern, internet-native version of the Norwegian social safety net. Rather than trying to solve everything at once, he strategically chose to start with one piece: health insurance. He then narrowed the initial customer segment to digital nomads—a group he knew intimately—creating a $45/month nomad insurance product that launched in 2018.

The journey from idea to market was deliberate. Sondra and co-founder Sergeant Hans talked extensively to potential users, who immediately flagged health as the top priority. The nomad insurance was elegant in its simplicity: global coverage for remote workers traveling internationally at an affordable price point. The first customers came directly through Safety Wing's website—individual digital nomads signing up for subscription plans. Within about a year, by 2019, the company hit $1 million in annual revenue.

But Sondra knew the original vision was larger. Safety Wing was just the first layer of a comprehensive global social safety net. In 2020, before COVID accelerated everything, they launched "Remote Health," a higher-priced product designed for companies wanting to offer health insurance to their distributed global teams.

The pivot from B2C nomad insurance to B2B remote health was unexpected. Sondra wasn't aggressively selling to enterprises initially—they came to him. After receiving the 100th inbound request from companies asking, "Can we buy this for our global team?," he realized he had to build it. They launched the enterprise dashboard in 2020 and it immediately resonated. SuperSide, his former company, eventually became one of Safety Wing's biggest customers—full circle from where the problem originated.

The COVID-19 pandemic was a mixed blessing. Many nomads evacuated, causing a temporary collapse in the nomad insurance segment. But the shift to remote work accelerated adoption of remote health insurance, especially after Safety Wing introduced COVID coverage. The result: 3X growth in five months by August 2020. What had been an existential crisis pivoted into an inflection point.

The company's growth strategy today focuses on multiple levers: improving customer acquisition, enhancing the claims experience (introducing a SafetyWing card to eliminate reimbursement friction), and scaling through ambassador programs and platform APIs. By focusing on the right segment and being responsive to market feedback—launching team plans when demand proved overwhelming—Safety Wing avoided the trap of being too rigid.

The pricing remained stable at $45/month for individuals since launch, with only modest inflation adjustments. The higher-priced Remote Health product for teams and individuals allowed the company to capture much more value from the market. With 25,000 active policies (a mix of nomads and team members), Safety Wing is doing roughly $2 million per month in revenue today—doubling year-over-year from a $12 million run rate to $24 million.

In 2022, Safety Wing raised a $35 million Series B at a $195 million post-money valuation—a 16x multiple on their $12 million ARR. Sondra deliberately timed this during a "plungy environment" (his word) in April 2022, when valuations were already compressing, avoiding the inflated multiples of 2021. Total funding is now $53 million across multiple rounds since their Y Combinator participation in 2018.

With a team of 60 (including 20 engineers), Safety Wing is focused on the long-term vision: building a truly global social safety net for the remote workforce. The company is investing in improving the customer experience—from direct hospital billing to the SafetyWing card—while simultaneously expanding to serve enterprise teams. Sondra's reflection on the journey: "Go straight for the thing that I most wanted instead of like a learning path." That's exactly what Safety Wing has done—solving a real problem for a real market, one customer segment at a time.