Staff Software Engineer, LearnWith.AI (Remote) - $200,000/year USD

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

• TimeBack: An educational platform that drives Alpha School's 2-hour learning model, delivering 99th percentile test outcomes.
• Incept: A content generation platform responsible for producing all personalized educational material across multiple learning applications deployed at Alpha School.
• Crossover: An AI-driven hiring platform that processes tens of thousands of monthly applicants, supporting global staffing for schools and companies.
  
  

You will take ownership of one of these platforms and dedicate the majority of your time to implementing the most complex components of the codebase with a compact team (3-5 experienced engineers, no junior developers). Your architectural choices directly influence whether other teams can build new applications rapidly, integrate seamlessly, and deliver value to students. Correct decisions unlock significant leverage. Poor decisions lead to integration failures and degrade velocity across multiple teams.

You are responsible for both building and operating what you design. You define quality standards and establish patterns for your platform. We follow a spec-driven approach: design precedes implementation, and planning always comes before building. You will have high autonomy, with no committees or review boards. This is a small, cohesive team where you are accountable for what you deliver.

What You Will Be Doing

• Technical Leadership: Define strategic architectural choices and set technical patterns that guide the team.
• AI Leadership: Champion the adoption of emerging AI workflows and develop impactful playbooks.
• Implementation: Construct the intricate, high-risk components of the codebase in collaboration with your team.
• Quality Reviews: Validate that your team adheres to established patterns and upholds quality standards.
  
  

What You Won’t Be Doing

• Functioning as an architect who does not implement
• Spending time in prolonged meetings
• Managing people (this role focuses on technical leadership, not personnel management)
• Maintaining legacy systems or internal IT infrastructure
  
  

Basic Requirements

Staff Software Engineer key responsibilities

• A minimum of 5 years of professional software development experience delivering software products
• A minimum of 3 years in a role as either a lead engineer (conducting code reviews) or architect (driving key technical decisions)
• Demonstrated experience working on platform-level products where other teams integrated with your APIs
• Strong engagement with AI tools, with a track record of active experimentation and exploration
  
  

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-AE-Dubai-StaffSoftwareE.006