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

We are operating platforms that serve thousands of students and teams in production:

• TimeBack: An educational platform that supports Alpha School's 2-hour learning model (achieving 99th percentile test outcomes).
• Incept: A content generation platform responsible for producing all personalized educational materials across multiple learning applications deployed at Alpha School.
• Crossover: An AI-powered hiring platform that processes tens of thousands of candidates monthly, enabling staffing for schools and companies on a global scale.
  
  

You will take ownership of one platform and dedicate the majority of your time to constructing the most technically demanding 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 build new applications quickly, integrate seamlessly, and deliver value to students. Correct decisions unlock substantial leverage. Poor ones generate integration complexity and reduce velocity across the organization.

You are responsible for both building and operating the systems you design. You define quality standards and technical patterns for your platform. Our process is specification-driven: design precedes implementation, and planning always comes before building. You will have high autonomy, with no committee approvals or review boards. This is a small, focused team where you are directly accountable for what you deliver.

What You Will Be Doing

• Technical Leadership: Define strategic architectural approaches and set technical standards that the team follows.
• AI Leadership: Champion the integration of emerging AI workflows and produce high-value playbooks.
• Implementation: Develop the intricate, mission-critical sections of the codebase together with your team.
• Quality Reviews: Validate that your team adheres to established patterns and upholds quality benchmarks.
  
  

What You Won’t Be Doing

• Acting as an architect who never writes code
• Spending time in continuous meeting cycles
• Managing people (this position focuses on technical leadership, not personnel management)
• Maintaining legacy systems or supporting internal IT infrastructure
  
  

Basic Requirements

Technical Lead key responsibilities

• A minimum of 5 years of professional software development experience delivering software products
• At least 3 years serving as either a lead engineer (conducting technical reviews of others' work) or architect (driving critical technical decisions)
• Proven experience building platform-level products where other teams integrated with your APIs
• Strong 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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5106-US-SandySpr-TechnicalLead.033