Preston Wickersham

When it comes to digital nomadism, Sam Matthew has walked the walk. 

Today, he heads the legal team at OnDeck, a platform for entrepreneurs with a fully distributed workforce. Before that, he was general counsel for Remote Year, a company that facilitates travel for those working remotely. 

In this role, Sam witnessed many of the challenges of facilitating the employment of digital nomads firsthand: he himself worked across 20+ countries in a three year period, linking up with other Remote Year employees in Latin America, Europe, and Asia along the way.  

Here he shares with Job some of the key lessons he took from his travels, including the different approaches one can take toward tourist visas and work permits. He explains how countries across the world will have very different approaches to digital nomads, from some that are creating laws to encourage nomadism to others that legally oppose the practice.

The conversation also turns to the legal difficulties companies can run into when hiring abroad, from complying with health and safety regulations to discovering the difficulties of terminating a contract. 

How to be a legally compliant digital nomad with Sam Matthew

In this conversation, Job and Tara discuss how digital nomadism provides unique legal challenges for employers, including tax codes, information security, or health and safety compliance. They discuss the Covid-19 pandemic’s impact on law, ushering in a new era of “Zoom court” in Canada. And Tara recalls becoming the first Canadian lawyer to serve a statement of claim through Instagram! 

Legal challenges of remote working with Tara Vasdani

SafetyWing CEO Sondre Rasch joins Remote Talks to discuss the challenges of offering benefits to contractors around the world and to discuss his philosophies on remote work leadership.

Remote Talks: Episode 13 with Sondre Rasch - Freelancers, Nomads, and Benefits

This week, Ellen Pao (CEO of Project Include) and McKensie Mack (CEO of MMG) join Remote CEO Job van der Voort to discuss their new report on harassment in remote workplaces and share strategies for companies to create welcoming remote environments for all.

Remote Talks: Episode 12 with Ellen Pao and McKensie Mack - Creating People-First Remote Workplaces

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment. This week, Remote VP of Growth Elisa Rossi hosts the show with special guest Sarah Aviram. The author of Remotivation, Sarah is a Fortune 500 HR expert as well as a passionate advocate for remote workers.

Remote Talks with Sarah Aviram - Living a Better Remote Work Life

In this episode of Remote Talks, Hopin's head of remote Jonathan Killeen joins the show to talk about his new role and the future of the events industry.

Remote Talks with Jonathan Killeen - Events and the Head of Remote Role

Allison Barr Allen, co-founder and COO of Fast, joins the show this week to talk about Fast Flex, hybrid remote workplaces, and how to get more women in positions of leadership. 

Remote Talks with Allison Barr Allen - Hybrid Remote and Women in Leadership

Tigran Sloyan joins the show this week to talk about bias in hiring, the wrong (and right!) ways to conduct interviews, and how to measure the success of talent acquisition teams.

Remote Talks with Tigran Sloyan - Improving Interviews and Evaluating Talent Teams

Remote Talks is a series of video interviews with the brightest minds in remote work and global employment, hosted by Remote CEO Job van der Voort. This week, we welcome Mac Reddin, founder and CEO of Commsor, a company tackling a unique challenge: building community and empowering people to nurture those communities. 

Remote Talks: Episode 7 with Mac Reddin - Nurturing Communities and Empowering Community Builders

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