Head Of Engineering

Summary

Join Outschool as an exceptional engineering leader to drive technical innovation and transformation, focusing on AI/ML-driven personalization and recommendations. This role requires deep engineering expertise and strong cultural leadership, with a proven track record of transforming engineering organizations or building high-performing teams. You will lead technical strategy, drive engineering excellence, scale technical operations, and build a world-class engineering team. The ideal candidate possesses extensive AI/ML expertise, strong coding abilities, and significant leadership experience. This is a hands-on, strategic role with a focus on using technology to drive significant business impact and report to the Head of Outschool/CEO.

Requirements

• 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

Responsibilities

• 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

Preferred Qualifications

Preference for SF/Bay area or a willingness to travel regularly for in-person time with our team

Benefits

• Competitive salaries, stock options, and investment plans that make saving for retirement easier
• Comprehensive health, dental, vision, disability, and life insurance coverage options for employees and their families. Our medical benefits include fertility and family planning coverage. We also provide employees with online access to coaching and therapy sessions through our partner, ModernHealth
• PTO and family leave enable our team to take the time that we need to recharge, relax, and spend time with family and friends
• With a team distributed across the US and Canada, we create a remote culture through expensable meals, virtual events, expensable home office setup, and internet allowance
• Annual budgets to self-direct our professional development as well as DEI learning. There’s also a budget for employees’ learners to take classes on Outschool!
• Outschool matches employee donations to established charities and has committed to support Outschool.org’s non-profit programs