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.
Similar Companies
Active Campaign
$4.2M/moActive Campaign started in 2003 as an on-premise email marketing solution built by Jason Vanderboom to fund his fine arts degree. After 10 years and 8 employees generating a couple million in revenue, he transitioned to a SaaS model starting at $9/month. The company now has over 60,000 customers generating over $50 million annually and employs 330 people, growing primarily through organic adoption, partnerships, and focus on the SMB market despite pressure to move upmarket.
Ahrefs
$3.3M/moAhrefs is a bootstrapped SaaS company providing SEO and backlink analysis tools, currently generating over $40M ARR with 45 employees. After joining in 2015, Tim Solo transformed the blog from 15,000 to 250,000+ monthly Google visitors by shifting from publishing what they wanted to write about to targeting keywords people actually search for, creating high-quality content with direct product integration, and continuously updating articles to accumulate backlinks. The company breaks conventional marketing wisdom by not using customer personas, growth hacks, or detailed analytics—instead focusing entirely on product quality and audience education through blog content.
NutriSense
$3.3M/moNutriSense is a direct-to-consumer metabolic health platform that pairs continuous glucose monitoring devices with proprietary software analytics and dietitian coaching. Launched in September 2019 with pre-sales in keto and Oura Ring Facebook groups, the company grew from under $1M MRR a year ago to $3.3M MRR today (3x growth), with 15,000-16,000 active paying customers and 170 employees. The business has raised $32M in funding across multiple rounds since a $250K seed in early 2020.
Solides
$2.6M/moSolides is the leading HR tech platform for small and medium companies in Brazil, providing talent management software for hiring, development, and retention. Founded in 2010 but pivoted to a subscription model in 2015, the company achieved $31.2M ARR as of March 2023 (100% growth YoY) with 20,000 paying customers managing close to 2 million employees. Alessandro Garcia raised a $100M Series B at an $800M valuation in 2022 and is targeting a $60M run rate by end of 2023, with plans to IPO once reaching $200M in revenue.
Calendly
$2.5M/moTope Awotona founded Calendly after three failed startups taught him the importance of solving real problems rather than chasing money. He spent six months validating the scheduling tool idea by studying competitors' products and user forums, then went all-in by emptying his bank account and hiring engineers in Ukraine. Calendly achieved product-market fit through a freemium model that optimized for invitee experience, growing to 4 million users and $30M ARR largely through organic viral growth and word-of-mouth.