154: Remote Year President Sam Pessin on Diversity, Equity & Inclusion and Building the World’s Largest Work-Travel Program

The Maverick Show with Matt Bowles

Sam Pessin talks about his international upbringing in London, Jerusalem and Beijing, and how that impacted his life and his passion for travel. He then talks about his professional career trajectory and ultimately deciding to co-found Remote Year in 2015. Sam takes us through the evolution of Remote Year, refining the customer experience, scaling it to over 100 employees by 2019, and being acquired by Selina in 2020. He then describes the current Remote Year offerings, ranging from one week retreats and one month workations to 4 and 12 month work-travel programs with a community of location independent professionals. Matt shares his experience on the 12-month Remote Year program in 2016 and why it was the best year of his life. Sam then describes the customer experience on Remote Year programs today and discusses safety, inclusion, positive impact, local immersion, and community building. Matt and Sam also discuss the Remote Year alumni “Citizenship” program and why it is one of the most valuable parts of the Remote Year experience. Sam then talks about the company’s Diversity, Equity and Inclusion priorities, and the progress Remote Year has made on its DEI goals over the last two years. He then opens up about the impact that the pandemic had on Remote Year, the acquisition by Selina in 2020, his current role as President, and his vision for the future of Remote Year. Next, Sam talks about Remote Year’s process for hiring amazing people, building company culture in a remote environment, and gives his tips on executive leadership. He then shares his personal productivity habits, how he manages stress, his biggest lessons learned from building Remote Year, and what he would do differently if he had to do it all over again. And finally, Sam shares his #1 Remote Year memory. FULL SHOW NOTES AVIALABLE AT: www.TheMaverickShow.com

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