Deliberate Detour invites you to grow with us! We’re seeking a talented person who understands how to build a program or project, but more than that, we’re looking for someone who loves what we do! The most important characteristics in candidates are a passion for and interest in furthering our programs.

Candidates should know that we function as a start-up. We’re scrappy. Our ideas change. A task we spend hours on may be jettisoned. Things don’t always go the way we want. Sometimes we fail. Sometimes our ideas are awful. We continue to learn. We evolve as we learn more about the subset of worldschoolers we serve and what they desire. We’re in it together. Every team member’s voice matters, and all ideas are considered.

Additionally, we plan to grow. This means that a part-time position may evolve into something long term, full-time, and full of responsibility, challenge, excitement, and creativity.

As such, candidates should be

  • Comfortable with change
  • Able to flesh out parameters of a project with minimal direction
  • Excited to offer new ideas
  • Ready to brainstorm and problem-solve
  • Delighted to work with a team of creative, passionate individuals
  • Able to find positivity when we fail
  • Committed to sticking with us as we grow

Position Overview

The Program Associate is a part-time contractor who supports other program staff in building and executing flawless, powerful, life-changing programs. Working closely with each country’s Hub Developer and the Founder, the Associate’s primary tasks include helping build complex months of programming, researching opportunities, ensuring reliable partnerships with local vendors abroad, troubleshooting when agreements dissolve, helping establish policies for families, communicating with parents, and preparing training sessions for local Hub staff.

The Associate should be incredibly detail-oriented, able to couple activities with desired impact, and a quick, efficient, decisive worker. They need to be strategic, considering how their action fits into a larger tableau of goals and desired outcomes. They should be able to keep in mind the granular and the lofty all at once, executing their work on both levels.

The Associate should also have the highest conceivable level of fluency, communicating faultlessly, succinctly, and descriptively in English.

Results Statement: The Program Associate has done their job well when they adequately, promptly, and fully respond to the needs of Hub Developers who juggle and assemble multiple details for families before, during, and after hub experiences. Additionally, they serve as a positive, supportive, responsive face of the company to our parent consumers. The Program Associate’s output should always align with Deliberate Detour’s mission and vision.

Description of Services

Program Development & Execution (70%)

  • Support Hub Developers in uncovering resources and connections for various hub activities.
  • Develop and evolve protocols and procedures for hubs, including ensuring our Safety Plan is in place in each country.
  • Source supplies for hubs as needed.
  • Assist with creating and posting for hub-based staff positions.
  • Conceive of and develop training schedule for hub staff.
  • Provide support during hub months by troubleshooting and helping pivot quickly.
  • Share the role of on-call staff when programs run.

Customer Service (25%)

  • Assist with answering general questions from enrolled families.
  • Help research and provide answers to specific questions.
  • Support with writing and sending out information to enrolled families like the Family Handbook.

Communications (5%)

  • Contribute to our newsletter and social media efforts with appropriate, timely ideas for topics and drafted articles.

Candidate Requirements

  • Extensive experience with a combination of more than one of the following: off-the-beaten-track travel, cross-cultural immersion, parenting, homeschooling, worldschooling, and/or digital nomadism.
  • At least 18 months of full-time experience in program development, program management, or education. A degree is not necessary but should be mentioned in application materials if it exists.
  • Exceptional written and verbal communication skills, with the ability to craft compelling and concise messages.
  • Ability to furnish relevant, newer, longer written samples.
  • Spanish fluency a plus.

Work Requirements + Pay

The Program Associate is a part-time contractor who will begin with a six-month contract beginning in January 2024 with the possibility of extension. While the Associate creates their schedule, work hours, and work environment, Deliberate Detour anticipates the assigned work will take about 5 hours per week.

Work will be compensated with a monthly contract rate for an associate-level job commensurate with cost of living in the country in which our Associate lives. The Associate is guaranteed one spot in a Deliberate Detour Worldschooling Hub annually at a 50% discount, and up to two spots with that discount, if we have two openings.

What We Offer

  • A vibrant, multicultural, collaborative team of co-workers.
  • The right to determine the work hours in which to perform the duties effectively.
  • The ability to work from anywhere in the world.
  • The freedom to direct how work gets completed.
  • The possibility of a full-time, permanent, fulfilling position with Deliberate Detour.

To Apply

Email a CV or resume to Deliberate Detour Founder, Stephanie Tolk, at by January 15, 2024 to be considered. Please include a cover letter in the body of your email or as an attachment addressing the characteristics and skills we seek, and use the subject line “Program Associate.” Please let us know where you live and your nationality.