Modern Work is a podcast where people around the world talk about the work they do & how they got there.

Interview topics include careers, childhood hobbies, education, entrepreneurship, office culture, work-life balance, remote work, digital nomads, apps, tools, processes, workflow, strategy, and more. 

The host, Katherine Conaway, is a consultant, writer & traveler.

Jason Piersialla, Programs Team Manager at Remote Year

Jason Piersialla, Programs Team Manager at Remote Year

Listen to this episode via the audio file below, or on one of these platforms:

Jason Piersialla


Jason travels the world with Remote Year, helping to ensure a seamless journey for their Remotes. He was the Operations Manager for Battuta, Remote Year's second group, from February 2016 - January 2017, and is now a Programs Team Manager. Outside of work, he enjoys traveling to new places, going hiking, and meeting street dogs. 


Episode: Jason Piersialla, Programs Team Manager at Remote Year



  • Operations Manager for Remote Year Battuta (Feb 2016 - Jan 2017)
  • Grew up in suburbs of Chicago
  • Illinois State University - Political Science 
  • Interested in politics, public policy, and environmentalism
  • Grew up outdoors, going to national parks, dad worked at a zoo


  • Studied international relations, how the world works together, how policies are made and change things
  • Minored in Middle Eastern and South Asian studies
  • International relations courses might cover broad subjects like what the UN is and how it works, or something more specific like the Israeli-Palestinian conflict
  • Studied abroad senior year in Argentina, found a marketing internship in Buenos Aires, and stayed in Argentina (skipped graduation)


  • Got a job in Cambodia managing Soksabike, a social enterprise in Badumbang, at a company that trained local college students to speak English and give them work experience
  • Cultural differences of people wanting to take on management / leadership roles
  • Studied abroad earlier in college in Bangkok, Thailand, and chose it because it was essentially a free exchange program 
  • Making international travel a priority in life
  • Finding programs and scholarships and opportunities to do things & get financial help, but you have to seek it out
  • Moved back to Chicago after Cambodia, felt the pressure of settling down and getting a good job with insurance, doing odd jobs while applying 
  • Moved to Finland for three months working with huskies at a sled dog company; lived in a cabin with one other person in freezing cold - found the job via workaway
  • Got a job at a digital consulting agency, fully remote company, working in operations on company internal policy and procedures 
  • Being organized is often mostly about writing everything down & then sort it out
  • Got laid off and applied to “business” jobs in New York
  • Applied to work at Remote Year and got the job
  • The difference between applying to jobs just for the sake of getting a job vs. being really excited about a company & position

Remote Year

  • Becoming staff on Remote Year, developing the role along with the program evolving
  • Operations Manager for Remote Year: coordinate and execute everything for the group, facilitate relationships and events for the group on the ground, fulfilling the deliverables of the company (apartment, workspace, travel)
  • Our Remote Year itinerary in South America, Europe, and SE Asia (1 month in each place): Montevideo, Uruguay; Buenos Aires, Argentina; La Paz, Bolivia; Cusco, Peru; London, England; Prague, Czech Republic; Belgrade, Serbia; Split, Croatia; Kuala Lumpur, Malaysia; Koh Phangan, Thailand; Phnom Penh, Cambodia; Ho Chi Minh City, Vietnam
  • Challenges of joining a group like Remote Year, adjusting to international travel, working remotely
  • Remote Year “breaking” cities but also building up infrastructure and technological innovations
  • The benefit of Remote Year being a year-long experience is getting to recover from and grow through experiences and challenges together, we move forward from our hard moments and develop our relationships with each other
  • Remote Year 2 Battuta demographics: age 23 - 65, average age of 29
  • Transitioning from Operations Manager to Programs Team Manager, train and support program leaders
  • Managing time differences of working US hours while traveling in other time zones; Remote Year's two itinerary options
  • Being in (and breaking out of) bubbles as a traveler - whether that bubble is being alone, groups of people from hostels, or Remote Year
  • The benefit of Remote Year (the program and the network) versus traveling on your own
Thank you for listening!



Jason is still working for and traveling the world with Remote Year, now as a Programs Team Manager (helping with various groups instead of leading one). 

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