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

We are expanding platforms relied upon by thousands of students and teams:

• TimeBack: Educational platform driving Alpha School's 2-hour learning model (99th percentile test results).
• Incept: Content generation platform producing all personalized educational materials 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 will take ownership of one platform and dedicate the majority of your time to constructing the most complex components of the codebase with a compact team (3-5 experienced engineers, no junior members). The architectural choices you make will dictate whether other teams can quickly build new applications, integrate seamlessly, and deliver value to students. Correct decisions unlock massive leverage. Poor decisions generate integration failures and destroy velocity across multiple teams.

You design, build, and operate your own work. You set quality standards and define patterns for your platform. Our approach is spec-driven: design precedes implementation, planning comes before building. Expect high autonomy, no committees, no approval boards. You work within a small, focused team where accountability for what you deliver rests with you.

What You Will Be Doing

• Technical Leadership: Formulate strategic architectural choices and define technical patterns for the team to adopt.
• AI Leadership: Champion the adoption of emerging AI workflows and produce high-impact playbooks.
• Implementation: Construct the intricate, high-stakes components of the codebase working directly with your team.
• Quality Reviews: Verify your team adheres to established patterns and upholds quality standards.

What You Won’t Be Doing

• Serving as an architect without hands-on implementation
• Spending time trapped in endless meetings
• Managing people (this role focuses on technical leadership, not personnel management)
• Handling legacy maintenance or internal IT systems

Basic Requirements

Technical Lead key responsibilities

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

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-US-SandySpr-TechnicalLead.037