Technical Lead, LearnWith.AI (Remote) - $200,000/year USD

We operate platforms relied upon by thousands of students and teams daily:

• TimeBack: An educational platform supporting Alpha School's 2-hour learning model (delivering 99th percentile test outcomes).
• Incept: A content generation platform producing all customized educational material for various learning applications deployed at Alpha School.
• Crossover: An AI-driven hiring platform managing tens of thousands of applicants monthly, supplying talent to schools and organizations worldwide.
  
  

You will take ownership of one platform and dedicate the majority of your time to constructing the most intricate components of the codebase with a compact team (3-5 experienced engineers, no junior members). The architectural choices you make dictate whether other teams can swiftly develop new applications, integrate seamlessly, and deliver value to students. Correct decisions unlock enormous leverage. Poor choices generate integration failures and erode velocity across several teams.

You are responsible for building and operating what you architect. You define quality standards and establish patterns for your platform. Our approach is spec-driven: design precedes implementation, planning always comes before building. You operate with high autonomy—no committees, no approval boards. You work within a small, cohesive team where accountability for what you deliver is direct.

What You Will Be Doing

• Technical Leadership: Shape strategic architectural choices and define technical patterns your team will implement.
• AI Leadership: Champion the integration of emerging AI workflows and develop high-impact playbooks.
• Implementation: Construct the sophisticated, mission-critical sections of the codebase together with your team.
• Quality Reviews: Verify that your team adheres to defined patterns and upholds quality benchmarks.
  
  

What You Won’t Be Doing

• Acting as an architect without writing code
• Becoming trapped in continuous meetings
• Managing personnel (this position focuses on technical leadership, not people management)
• Handling legacy maintenance or internal IT infrastructure
  
  

Basic Requirements

Technical Lead key responsibilities

• A minimum of 5 years of professional software development experience delivering software products
• A minimum of 3 years serving either as a lead engineer (conducting code reviews for others) or architect (driving critical technical decisions)
• Experience delivering platform-level products where your APIs were consumed by other teams
• Active, deep involvement with AI tools, consistently experimenting and exploring new possibilities
  
  

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-5106-IL-TelAviv-TechnicalLead.032