Technical Team Lead, LearnWith.AI

Role overview

This position is for a Technical Team Lead who will take ownership of both product quality and delivery for application-layer products used by thousands of learners. You will lead a small group of 3 to 5 engineers while also contributing directly through hands-on development.

The role is split evenly between building and leading: half of your time will be spent delivering advanced features, and the other half will focus on mentoring, coaching, and helping the team perform at a high level. You will be expected to set quality standards, establish technical examples, review code with a teaching mindset, and help engineers continue improving. Team success is measured collectively, not just by individual output.

The team structure is intentionally lean, with a high degree of autonomy and very little process overhead. You will own technical leadership, while people-management responsibilities are handled elsewhere.

Products in scope

• Athena: an AI-based system for generating videos and assessments that produces measurable learning improvement.
• TeachTap: an AI-powered educational experience that brings historical figures to life in a short-form, TikTok-like format.
• TeachTales: an adaptive storytelling product built to strengthen reading comprehension.
• TrashCat: a game-based learning platform designed to make education more engaging and enjoyable.

What you will do

• Build sophisticated features that help shape the technical direction of your team.
• Review pull requests thoroughly and provide clear, educational feedback.
• Coach engineers through pair programming and constructive guidance.
• Lead technical initiatives and break down complex requirements into workable tasks.
• Set standards for quality and make sure the team follows them consistently.

What the role does not include

• Hiring, firing, performance reviews, or career-development conversations.
• Working on platform-level infrastructure.
• Heavy meeting load or meeting-driven routines.
• Designing architecture without also implementing it in code.

About the company

LearnWith.AI is an edtech startup that combines artificial intelligence with subject matter expertise to create a new learning experience. Its approach blends more than 50 years of learning science, modern data analytics, and AI-based coaching to help students learn more effectively, learn faster, and enjoy the process.

The company operates remotely first and hires globally through Crossover.

Working arrangement

This is a long-term full-time role with a 40-hour workweek. The position is available immediately. You will work as an independent contractor under a Contractor of Record agreement with Crossover. Compensation is set at USD 100 per hour, which works out to USD 200,000 per year based on 40 hours per week and 50 weeks annually. Payment is made weekly.

Additional information

Crossover job code: LJ-5738-CA-Toronto-TechnicalTeamL.003