The Remote Work Tribe Podcast: Jesse Schoberg


In this episode of the Remote Work Tribe podcast, we chat with Jesse Schoberg, Co-Founder, and CEO at

As a digital nomad since 2008, he shares his relationship with work, leadership, asynchronous communication, and management of fully distributed teams. This is a fantastic episode if you want to learn more about Jesse’s path working remotely for more than a decade, what works for him, and how to flow across time zones and workstyles.

In this episode, we discuss: 

  • What inspired Jesse to start DropInBlog. (1:30)
  • How did he prioritize projects and decide to go all-in with DropInBlog. (3:15)
  • Mindset shift from leading an agency vs. a SaaS product. (5:10)
  • How to allocate time and resources when running an agency and a SaaS product. (7:00)
  • Leadership style and async communication. (8:35)
  • Frameworks and mental models Jesse looks for when hiring new talent. (12:05)
  • Interviewing processes at DropInBlog. (13:40)
  • How Jesse found his co-founders for DropInBlog. (16:10)
  • Leading a team with partners and finding alignment. (19:45)
  • How leading an agency vs. creating a SaaS product has changed leadership dynamics. (22:30)
  • How was selling their smaller SaaS products before focusing all efforts on DropInBlog. (25:40)
  • His experience with diverse income streams and multiple jobs and how they shaped his work style. (27:25)
  • Team retreats at DropInBlog. (29:15)
  • How being a nomad changes your relation to work and your overall lifestyle. (32:35)
  • Lightning round questions. (35:30)

We hope you enjoy it!

Links mentioned on the podcast

By Sebastian Cuervo