The Remote Show · Tyler Sellhorn, Matthew Hollingsworth

Ryan Chartrand, CEO at X-Team

·29 min·2 clips

X-Team gives developers $2,500 a year to spend on anything that energizes them—from video games to weekend getaways.

1. The Remote Show host Tyler Selhorn interviews Ryan Chartrand, CEO of X-Team, a remote developer network serving brands including Fox Broadcasting, Riot Games, Beachbody, Coinbase, and Sony. 2. Chartrand founded X-Team 15 years before this recording (around 2006), making it one of the earliest fully distributed developer companies; its community spans 70 countries. 3. The episode's central argument is that the hardest part of remote work is not tools or process but avoiding isolation and maintaining energy — which X-Team has spent 15 years engineering solutions for. 4. X-Team's 'Unleash Plus' perk gives every developer $2,500 per year to spend on anything that energizes them: gym memberships, video games, weekend getaways, local meetups, or starting their own community. 5. The X Outpost is a monthly rotating co-living, co-working experience: X-Team sponsors a location, developers can live and work there alongside teammates, and the company funds local expeditions — including into jungles in Brazil. 6. Rather than one-size-fits-all team events, X-Team maps events to the individual passions of developers: StarCon, for example, brought in a top astronomer for exclusive Q&A, piano trivia on sci-fi songs, and a biking challenge modeled on Mars's Jezero Crater distance. 7. Chartrand distinguishes X-Team from an agency by framing it as a 'lifestyle experience' offering 'complete freedom, flexibility, and energy' — a distinction he says has made the company hard to explain but important to maintain. 8. The 'when they need it' philosophy means no experiences are forced: developers opt in to community activities, and participation is signaled through X-Team's digital currency system rather than mandatory attendance. 9. The currency is earned through 'bounties' — gamified challenges tied to personal passions, community activities, or professional habits — and spent on X-Team collectibles and experiences. 10. Onboarding uses bounties from day one: new developers receive challenges to introduce themselves, update their LinkedIn, and connect with passion-based sub-communities — getting them engaged before the culture feels abstract. 11. 'Houses' are Harry Potter-style micro-communities within X-Team, organized around shared values or interests: Chartrand belongs to House Ragnar, a group centered on Viking culture and beer. 12. Chartrand draws a historical parallel: online job boards in the late 1990s made switching jobs easy, triggering a retention crisis for companies — exactly the dynamic of today's Great Resignation following remote work adoption. 13. He projects a third freedom revolution 15-20 years ahead, predicting work will become even more flexible and people-centered, with 'doing more of what you love' as the default rather than an exception. 14. The defining remote skill Chartrand looks for is async proactive communication: writing Slack messages assuming a two-day reply delay, pre-answering follow-up questions, and providing conditional responses to avoid multi-day back-and-forth chains. 15. He gives a specific budget-approval example: instead of 'can we increase the budget?' triggering a request-response chain, the async version answers 'yes likely; if reason A, definitely yes; if reason B, I need to check.' 16. X-Team's tagline, 'Keep Moving Forward,' is directly tied to the async mindset: the goal is for remote workers to advance work even when collaborators are unavailable or asleep. 17. Chartrand argues that technical skill is the bare minimum for X-Team candidates; the differentiating factors are soft skills, and above those, remote-specific soft skills — proactivity and async communication mastery. 18. The episode is a conversational interview with Selhorn asking follow-up and clarifying questions; Chartrand drives most of the content and speaks at length about X-Team's philosophy and operations. 19. Remote workers and developers considering joining or building distributed teams will find Chartrand's specific practices — Unleash Plus, bounties, Houses, async rules — directly applicable. 20. Listeners looking for tactical guidance on remote tools, workflows, or enterprise remote policy implementation will find the episode high-level rather than prescriptive on those topics.

As heard by us

A straightforward reminder that remote work is about flexibility and control, not just lower costs.

Ryan Chartrand and X-Team come across as an early remote-work case study: high-performing developer teams on demand, a community spread across more than 70 countries, and a push for location-independent work that dates back to 2006.

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Why you'd press play

You want a grounded case for hiring remote teams without flattening the human side.

Read the full recommendation in PlayNext →

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