We're expanding platforms that support thousands of students and teams daily:
TimeBack:
Educational platform driving Alpha School's 2-hour learning model (99th percentile test results).
Incept:
Content generation platform producing all personalized educational content for multiple learning applications deployed at Alpha School.
Crossover:
AI-powered hiring platform handling tens of thousands of applicants monthly, staffing schools and companies worldwide.
You'll take ownership of one of these platforms and dedicate most of your time to building the most complex components of the codebase with a small team (3-5 strong engineers, no juniors).
Your architectural choices dictate whether other teams can build new apps quickly, integrate seamlessly, and deliver value to students. Execute this well and you unlock significant leverage. Poor decisions generate integration chaos and destroy velocity across multiple teams.
You build and operate what you architect. You define quality standards and patterns for your platform. We're spec-driven: you design before implementing, always plan before building. High autonomy, no committees, no review boards. Small tight-knit team, where you're accountable for what you deliver.
What You Will Be Doing
Technical Leadership:
Drive strategic architectural decisions and define technical patterns for the team to adopt.
AI Leadership:
Accelerate adoption of new AI workflows and develop high-impact playbooks.
Implementation:
Construct the complex, high-stakes components of the codebase with your team.
Quality Reviews:
Verify your team adheres to established patterns and upholds quality standards.
What You Won't Be Doing
Functioning as an architect without coding
Spending time in endless meetings
Managing people (this is a technical leadership position, not a people management role)
Maintaining legacy systems or internal IT infrastructure
Basic Requirements
Technical Lead key responsibilities
At least 5 years of professional software development experience building software products
At least 3 years as either a lead engineer (reviewing others' work) or architect (making key technical decisions)
Experience working on platform-level products where other teams consumed your APIs
Deep engagement with AI tools, actively experimenting and pushing boundaries
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 for more details on this topic.
Crossover Job Code:
LJ-5106-CA-Toronto-TechnicalLead.028
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