Technical Team Lead at Crossover

We are seeking Technical Team Leads to oversee delivery and quality for our application-layer products. In this role, you will guide a compact team of 3-5 engineers developing educational applications that serve thousands of students.

Potential Products Include

• Athena: AI-powered video and assessment generation delivering quantifiable learning outcomes
• TeachTap: AI-driven platform bringing historical personalities to life in a TikTok-inspired learning format
• TeachTales: Customized, immersive storytelling designed to enhance reading comprehension
• TrashCat: Game-based learning that makes education engaging and enjoyable

This position blends individual contribution with leadership: approximately 50% dedicated to hands-on development of sophisticated features, and 50% focused on mentoring and empowering your team. You will define quality expectations, create technical patterns, conduct code reviews with an instructional approach, and support engineer development. Team results fall under your accountability, extending beyond your personal contributions.

Compact team structure, significant ownership, minimal process overhead. Your focus is technical leadership; people management is handled separately.

What You Will Be Doing

• Developing sophisticated features that establish technical patterns for the team
• Conducting pull request reviews with comprehensive, instructional commentary
• Mentoring engineers through pair programming and constructive feedback
• Organizing technical initiatives and decomposing product requirements
• Defining quality benchmarks and ensuring team adherence

What You Won’t Be Doing

• Handling personnel management (recruitment, termination, evaluations, career development discussions)
• Building platform or infrastructure-level systems
• Attending excessive meetings
• Designing architecture without hands-on implementation

Basic Requirements

Technical Team Lead key responsibilities

• At least 5 years of full-stack development experience
• At least 2 years in a lead role (reviewing others' work, mentoring engineers, establishing team practices)
• Track record of shipping SaaS products
• Experience with AI tools in development workflow
• Demonstrated ability to help other engineers improve and grow

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.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

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.002