[Hiring] Head of Engineering @Outschool

We're seeking an exceptional engineering leader to drive technical innovation and transformation, with a special focus on AI/ML-driven personalization and recommendations for our marketplace. The ideal candidate will either have experience transforming engineering cultures or building high-performance engineering organizations from the ground up. This role combines hands-on technical leadership with strategic vision to scale our platform and drive significant business impact. This role will report into the Head of Outschool/CEO.

At Outschool, we’ve decided to take an unconventional approach to titles that aligns with our values and is more focused on impact above status - this role would typically be called a VP or SVP of Engineering and we are looking for candidates who bring that level of experience to the role. You can read more about our titling philosophy here. 

• Lead technical strategy and hands-on development of AI/ML capabilities, focusing on personalization and recommendations
• Drive engineering excellence through mentorship, best practices, and quality standards
• Transform or build engineering culture focused on learning, innovation, and high performance
• Scale technical operations while maintaining agility and innovation
• Architect and implement core platform capabilities
• Establish data-driven performance metrics aligned with business objectives
• Foster deep collaboration between engineering, product, and design teams
• Build and retain world-class engineering talent
• Drive technical decisions that create competitive advantages
• Lead evaluation and modernization of technical stack

You're a technical leader who combines deep engineering expertise with strong cultural leadership. You have a track record of either transforming engineering organizations or building high-performing teams from scratch. You're hands-on, strategic, and passionate about using technology to drive business impact.

• Deep expertise in AI/ML, particularly recommendation systems and personalization
• Strong coding abilities and system design experience
• 10+ years engineering leadership experience
• Led engineering organizations of 30+ people
• Track record of successful product launches in consumer marketplaces or consumer software is critical
• Experience scaling technical platforms
• Proven ability to attract, develop and retain exceptional talent
• Strong technical decision-making capabilities
• Excellence in stakeholder communication and management
• Preference for SF/Bay area or a willingness to travel regularly for in-person time with our team

Our organization is built on three core values that shape everything we do:

We value learning by doing, using startup methods, which inherently means embracing risk and change. We look to the future rather than holding onto the past. We are positive, bold and resilient to setbacks. We hone our craft by trying new approaches and learning together.

We value scaling to grow our impact for many more learners. Achieving scale requires building a large, profitable, global business to enable our mission for the long-term. We use our scale to better understand, and sustainably serve, the broad and diverse needs of all learners.

We value disrupting the status quo in service of our mission. The status-quo education system is unacceptable to us, so we are willing to embrace challenge, discomfort and even controversy in service of fast progress. We make hard decisions, take ownership and bias towards action.

These core values manifest in how we work every day:

• Embrace experimentation and calculated risks
• Learn through rapid iteration and feedback
• Stay resilient through setbacks
• Focus on continuous improvement

• Build for growth while maintaining quality
• Make data-driven decisions
• Think strategically about long-term scalability
• Balance speed with sustainability

• Push boundaries in technical solutions
• Challenge status quo when needed
• Maintain strong opinions, loosely held
• Embrace and drive transformation

• Actively participate in technical discussions
• Deliver high-quality output
• Remove obstacles for the team
• Maintain attention to detail

• Prioritize long-term company success
• Make decisions aligned with strategic goals
• Focus on collective impact
• Build for the greater good