Technical Team Lead

About LearnWith.AI

LearnWith.AI is an edtech startup that leverages AI and subject matter experts to cultivate a new way of learning. Our unique approach leverages 50+ years of learning science, cutting-edge data analytics and AI-powered coaching. In doing so, we can help students learn more, learn faster, and learn better - and have fun while doing it. We are a remote-first company that hires globally via Crossover.

Role Overview

We are seeking Technical Team Leads to oversee delivery and quality for our application-layer products. You will manage a compact team of 3-5 engineers developing educational applications utilized by thousands of students.

This position blends individual contribution with leadership: you will spend 50% of your time implementing sophisticated features hands-on, and 50% guiding and developing your team. Your role includes defining quality expectations, creating technical patterns, conducting instructional code reviews, and facilitating engineer development. Team success is your responsibility, extending beyond personal code contributions.

Lean team structure, substantial autonomy, minimal administrative overhead. Technical leadership is yours; people management resides elsewhere.

Sample Products In Your Potential Portfolio

• Athena: AI-driven video and assessment generation producing quantifiable learning gains
• TeachTap: AI-powered platform reimagining historical figures in a TikTok-inspired educational format
• TeachTales: Customized storytelling experiences designed to enhance reading comprehension
• TrashCat: Game-based learning platform making education enjoyable and interactive

What You Will Be Doing

• Implementing sophisticated features that serve as technical examples for your team
• Conducting pull request reviews with comprehensive, educational commentary
• Developing engineers through pair programming and constructive feedback
• Organizing technical initiatives and decomposing project requirements
• Defining quality benchmarks and enforcing team adherence

What You Won’t Be Doing

• Handling HR functions (recruitment, termination, performance evaluations, career planning)
• Building platform or infrastructure-level systems
• Attending continuous meeting schedules
• Designing architecture without hands-on coding

Basic Requirements

Technical Team Lead key responsibilities

• Minimum 5 years of full-stack development experience
• Minimum 2 years in a leadership capacity (conducting code reviews, mentoring developers, defining team standards)
• Proven history of delivering SaaS products
• Practical experience incorporating AI tools into development processes
• Verified capability to elevate other engineers' skills and performance

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5738-CA-Toronto-TechnicalTeamL.001