Head of Teaching and Learning

Fiveable - Milwaukee, Wisconsin or Remote - Full time

As the head of teaching and learning, you will direct all of our educational experiences both online and in-person for students and teachers. This includes overseeing our team of content managers, creators, and streamers, aligning our content to applicable standards, and optimizing the Fiveable learning experience.

Fiveable is headquartered in Milwaukee, WI. The head of teaching & learning can either be based in Milwaukee or work remotely.

Here are a few links to learn more about the company we are building and our journey so far:

👩🏽🏫 https://www.edsurge.com/news/2019-05-06-a-former-oakland-unified-teacher-now-helps-even-more-students-pass-ap-tests

🥳 https://fiveable.me/press/fiveable-fundraising-2019/


  • Collaborate with Fiveable team members to optimize all content and product designs based on College Board standards and teaching best practices
  • Manage the workflow of content production for live-streams, trivia, and all articles
  • Lead the team of content managers to maintain an active calendar of events & content
  • Recruit and hire new content creators, streamers, editors, and illustrators as needed
  • Develop resources to onboard, train, and continuously support the content team
  • Maintain organized documentation, bios, and payment information for the content team
  • Plan and execute events to build relationships with teachers like summits and happy hours
  • Analyze data to understand the learning needs of Fiveable users


  • 3+ years experience teaching an AP subject, ideally with experience as a reader
  • Proven track record as an effective team leader
  • Organized and detail-oriented with strong communication skills


  • 💰 Competitive compensation
  • 🎈 Equity .5-1%
  • 👓 Health, dental, and vision insurance
  • 🛋 Flexible work schedule and paid time off

...but most of all, you'll play a pivotal role in helping thousands of students build confidence for AP exams.

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Curriculum Design

Experience Level

Mid Level


Fiveable is a social learning platform where high school students study, collaborate, and engage after school. With a supportive community, interactive content, and practice questions, we’re the most fun all-in-one option for students studying for AP exams and beyond.

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