Digital Learning Fellowship


The education fellow will work closely with the founder to develop a thoughtful learning experience for students and teachers. The primary focus will be to manage a robust calendar of live streams hosted by high quality streamers. As we scale to include more subjects and more streamers, the fellow will play a critical role in developing systems and processes to recruit, on-board, engage, and develop streamers. This includes managing monthly summits for streamers to build community and share best practices across disciplines. The fellow will also work with the streamers to manage and organize the growing database of resources to create seamless experiences for students and teachers as they search for materials. Finally, the education fellow will work to strengthen connections between Fiveable and school networks by creating new partnerships and supporting feedback loops within the pilot program. This fellowship is an opportunity to gain experience in digital learning and education technology while also developing skills in teaching, event planning, and content management.

Day to Day:

  • Create processes to recruit and on-board high quality streamers that diversify the content.
  • Support streamer development through post-stream check-ins and observations.
  • Identify and document best practices for streamers.
  • Plan and manage monthly professional development summits for stream teams.
  • Work with streamers to manage the post-production flow of content.
  • Keep the resource database organized and identify new content opportunities.
  • Work with the founder to create a standardized live stream lesson structure.
  • Support the pilot program by relaying teacher feedback to Fiveable team members.
  • Reach out to schools to create partnerships and develop brand awareness.
  • Create weekly reports on live stream attendance and engagement metrics.

Your Background:

  • You have completed at least two years of undergraduate coursework.
  • You have a basic understanding of the challenges and opportunities in secondary education and a passion for hybrid and collaborative pedagogical approaches.
  • You have some experience in the field of education through tutoring, summer camp, coursework, teaching, etc.
  • You have strong interpersonal, verbal and written communication, and creative skills.
  • You have a proven ability to manage multiple projects at a time and meet deadlines in a fast-paced work environment.
  • You have an entrepreneurial spirit and a demonstrated capacity for strategic thinking, creative problem solving, and the ability to achieve tangible results.
  • You are comfortable with Google Suite tools.

Bonus Points:

  • You have experience as an AP student or teacher in any subject, preferably in STEM.
  • You have an undergraduate or graduate degree in the field of education.
  • You are extremely comfortable with other tools that we frequently use such as Slack, WordPress, and Proofhub.

Compensation & Benefits:

This is a unique opportunity to join an early-stage startup and work closely with the founders to develop a range of professional skills. After a full semester of the fellowship, fellows may be offered full-time positions or may extend their fellowship for an additional semester.

  • Full rent and utilities covered for the house plus Netflix & Hulu!
  • Groceries for the house and monthly outings with the team
  • Weekly team dinners at Fiveable HQ
  • Monthly stipend and end of semester bonuses

Note: Recent graduates and alumni of area colleges are heavily encouraged to apply. We regret that we are unable to accept overseas applicants + cannot provide sponsorship for work visas at this moment.

Read more about Fiveable and the founders’ mission at:

Job Category: Education
Job Type: Full Time
Job Location: Milwaukee

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