Director of Education

Telecommute · Boston, Massachusetts, United States · Boston


We are looking for someone to lead all education products at thoughtbot. Currently, this includes our online education site Upcase and our books. It could be expanded to include our podcasts, in-person workshops, and other areas related to education. As Director of Education, you will have the agency to choose the exact responsibilities of the role and future growth, including making changes to the existing services and potentially adding new ones.

thoughtbot has been providing training since 2008. In 2012 we began to move our in-person workshops online, along with other education materials, and in 2014 we gave our online community a brand of its own: Upcase. Over that time, our education efforts have progressed from helping dozens of people a year to a thriving community of thousands of developers that not only take our online workshops, but work with us and each other to improve and maintain their development skills. These products and services combined have had over 10,000 customers and just under $2mm of revenue.

In 2011 we published our first book available for individual purchase, Backbone.js on Rails, which has been purchased by over 3800 people. Since 2011 we have released 10 other books on a range of topics from Ruby to DNS. From the beginning, we have sought to do something different with our books. By using Markdown and GitHub to author the book and giving early repository access to purchasers as we write, readers can follow along, view diffs, comment on individual lines of the work, and use Github Issues to provide feedback.

We believe that there is a better way to do development and we want to bring that to as many people as possible. As Director of Education you will be a core part of that mission, taking ownership over these two businesses and more, and helping to take them to the next level.


The ideal candidate will have experience with:

While a background in Rails development is preferred, and the opportunities for doing development on these products exist, this is primarily a product management and business growth position and not a developer position. While your development skills will be useful in achieving product goals, the product management, content production, and growth will your primary day to day focus.

Boston is the preferred location for this position (our recording studio is here), but any city where we have an office could work, and we will also consider well-qualified remote candidates.


The position includes a competitive salary with benefits, relocation assistance, and stock options.

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