Director of Engineering, Teachable

• We’re seeking a pragmatic, growth-minded leader who thrives in fast-paced, agile environments and knows how to balance innovation with technical rigor
• 10+ years of engineering experience in product-focused tech companies, with 5+ years managing engineering teams (including other managers)
• A track record of delivering customer-facing products in an agile, iterative environment
• Strong communication and collaboration skills — able to partner with cross-functional leads and executive stakeholders
• Deep technical expertise in web application development, with experience in service-oriented architectures. Familiarity with frameworks like Ruby on Rails is helpful, though our future is increasingly focused on technologies like Next.js and Go
• Experience evolving complex systems and legacy codebases toward modern, maintainable architectures

Desirable

• Teachable is looking for a seasoned Director of Engineering to lead our Core Engineering Team – the group responsible for the learning experience at the heart of our platform
• This includes everything from course creation and delivery to the learner experience across web and mobile
• As a key member of our Engineering Leadership, you’ll guide cross-functional teams in building intuitive, high-impact features for our customers and their students
• You’ll collaborate closely with Product and Design, shape technical strategy, and play a central role in evolving our architecture from a monolith to a more modular, service-oriented system
• This role reports to the VP of Product & Engineering and will manage multiple engineering managers and individual contributors
• Lead, mentor, and grow an organization of ~30 engineers, developing strong managers and high-performing teams
• Collaborate closely with Product and Design to define and deliver a roadmap that balances innovation with reliability and scale
• Own technical direction and architectural decisions for the Core experience — including identifying opportunities to break apart our Rails monolith into modular, scalable services
• Establish engineering best practices and ensure high standards of quality, security, and observability across the stack
• Contribute to org-wide engineering strategy and planning in collaboration with other functional leads