Why Gig Work Is The Future Of Work & How To Lead A Virtual Team

Today my guest is Sondre Rasch. Sondre is co-founder and CEO of SafetyWing, a membership-based global social safety net for remote workers and teams. He previously co-founded Superside, a platform that helps freelance designers collaborate and complete design projects for enterprise companies. Both startups have received funding from Y Combinator, whose previous investments include Airbnb, Door Dash, Stripe, Instacart, Dropbox, and Coinbase. After receiving his Master of Science from the Norwegian School of Economics, Sondre developed new education and social policies for the government of Norway.

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Entrepreneurial Upstart to Startup Success

Growing up in Norway, Sondre’s flair for enterprise emerged by the time he was a teenager when he started a web hosting company in his childhood bedroom with his mobile phone providing customer support. While at university, Sondre studied economics and computer science before going to work as a governmental advisor on social and education policy. Ultimately frustrated by the pace of change, he returned to the world of startups, first as a co-founder at Superside, a collaborative tool for freelance designers, and most recently launching SafetyWing, a platform through which companies can administer health insurance benefits for remote teams in today’s increasingly nomadic workplace environment. Both ventures have received backing from Y Combinator (the investor behind such success stories as Airbnb, Door Dash, Dropbox, and Instacart).

The Gig Economy: Factors and Forecast

The pandemic has challenged and reshaped the gig economy, redefining remote worker status. Sondre shares thoughts on the new hybrid model, which he says have fostered 40 percent annual growth in the freelance sector. “Being able to use freelancers or freelance pools for the right functions can make your company more productive and flexible,” he explains. It makes sense for contract employees, who want the flexibility and freedom gig work offers and is both a cost-saver and practical tool for companies that want to remain nimble. Whether labeled “freelance” or “remote worker,” these distributed relationships are exploding, along with cultural impacts, adaptations, and a need for platforms like Superside and SafetyWing.

What It Takes to Build an Effective Virtual Team

Sondre has learned first-hand, through his startup ventures, what it takes not only to build but scale and sustain effective teams. His best practices include:

#1 Get Clear Right from the Start: From the outset at SafetyWing, Sondre and his co-founders took the time to establish a guiding vision. They articulated overarching goals and ensured that their values aligned. If those guardrails are well established for all to see, Sondre says, a unity of purpose smooths coordination and minimizes the kind of chaos that can crop up across workplace geographies, cultures, projects, and timelines. It doesn’t have to be a huge investment of time, but it’s critical to set priorities and get buy-in on those goals. As a result of that early intentionality, Sondre has seen SafetyWing grow and evolve relatively seamlessly into a mission-driven, values-focused company.

#2 Be Intentional about Cadence: Sondre and his team pay close attention to the balance, style, and content of communications. When the foundational vision is clear to everyone in the company, Sondre has found the need for constant, interminable meetings are drastically reduced. It’s no longer about meetings. It’s about coordination, cohesiveness, and culture. There are multiple tools to support collaborative work: Google sheets available for all members of a team to see and repurpose as necessary. A standing (but limited) rotation of predictable weekly meetings within timeframes that work across multiple time zones. “Digital Cleanup” dates to work as a team to clear out stale, duplicative or messy data on channels such as Slack. Free-wheeling company-wide Town Hall-style meetings without a set agenda or more intimate meetings that foster icebreakers and community, especially for remote workers who are feeling isolated. There are all kinds of cadences, says Sondre, but whichever you’re deploying at any given time should be executed thoughtfully to avoid tedium and burnout among freelance and remote workers who value their time.

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#3 Apply the Right Model. Teams within a startup culture should not be expected to adopt strategies better suited to larger, more entrenched enterprises. Avoid getting top-heavy, creating roles, and growing teams prematurely. Staying lean and focused helps cut down on “useless bureaucracy.” Startup teams need to be focused on concrete, short-term qualitative goals (fleshed out with quantitative data); not processes. Ultimately, as a startup matures, qualitative goals will evolve into a fully fleshed-out product roadmap with detailed quarterly goals. But all along the way, weekly goal-setting and tracking are critical to momentum for the whole team — whether virtual or onsite.

#4 Monitoring Productivity: It’s About Leadership and Judgment

The go-to for managers conditioned to full-time traditional workplace environments is control — or the illusion of it. It’s hard to validate that someone is in their cubicle when that workspace is a hundred or a thousand miles away. Some executives keep an eye on workers through surveillance devices (random screenshots, keystroke loggers, or other tracking software). But in his experience, Sondre doesn’t think it’s the way to go. At SafetyWing they went with a paradigm shift: Instead of measuring input, they measure outcomes. Are their freelancers on schedule and on point? It can be more labor-intensive and interactive, requiring initial goal setting and road mapping, but the time is well invested. Sondre’s approach has resonated and built mutual trust as well as productivity among his virtual teams. Advice for adapting to this change: Resist the urge to suffocate freelance or remote workers with check-ins and monitoring that serves no ultimate purpose. “It starts with a decision,” says Sondre. “You just have to take a big step into the unknown. If you’re the type of leader who only thinks people are working if you can see them, then honestly you’re not going to be able to lead the team.”

The Future of Work Without Geographic Constraints

Sondre predicts gradual but significant population redistribution over the next five years as a result of the shift to remote work. Much like the advent of the automobile once drove suburban development, the virtual workplace is opening up an entirely new landscape. “What I’m seeing from on the frontier is people are starting cities, people are starting towns, people are starting Nomad hotels, remote work villages,” he says. Remote workers under this new model can follow their bliss, base their lives where they long to be instead of where jobs dictate they reside. This shift has generated new market opportunities for companies like SafetyWing, which offers health and travel insurance vehicles for freelance and distributed workers (domestic and internationally). It’s subscription-based ($42 per month), offers flexible terms, and covers remote teams in a variety of circumstances through a simple benefits dashboard app.


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SafetyWing is your home country online. They are building a global social safety net for remote workers worldwide: from health insurance and remote retirement to a truly borderless world.

List of products they have:

– Nomad Insurance is travel medical insurance. They cover people from all over the world, while outside their home country.

– Remote Health, their full global health insurance solution, can cover everyone in the remote companies’ teams, no matter where they are in the world, all under one plan. Remote Health insurance works globally, so you can hire the best talent in the world.

SafetyWing Product Roadmap: Remote Doctor, Remote Retirement, Disability Coverage, Remote Therapist, Parental Leave, Income Protection, Life Insurance.





4x Best-Selling Author, Speaker, & Futurist. Founder of FutureOfWorkUniversity.com. Exploring Leadership, Employee Experience, & The Future of Work

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Jacob Morgan

Jacob Morgan

4x Best-Selling Author, Speaker, & Futurist. Founder of FutureOfWorkUniversity.com. Exploring Leadership, Employee Experience, & The Future of Work

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