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 supporting Alpha School's 2-hour learning model (99th percentile test outcomes).
• Incept: A content generation platform producing all personalized educational materials for multiple learning applications deployed at Alpha School.
• Crossover: An AI-powered hiring platform managing tens of thousands of applicants monthly, staffing schools and companies worldwide.
  
  

You will take ownership of one of these platforms and dedicate the majority of your time to building its most complex components with a small team (3-5 senior 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 significant leverage. Poor decisions lead to integration failures and slow down multiple teams.

You design, build, and operate your own work. You define quality standards and establish 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, cohesive team where accountability for what you ship rests with you.

What You Will Be Doing

• Technical Leadership: Define strategic architectural choices and set technical patterns the team will follow.
• AI Leadership: Champion adoption of emerging AI workflows and develop high-impact playbooks.
• Implementation: Construct the complex, mission-critical portions of the codebase with your team.
• Quality Reviews: Verify that your team adheres to established patterns and upholds quality standards.
  
  

What You Won’t Be Doing

• Acting as an architect without writing code
• Spending time in continuous meetings
• Managing people (this role focuses on technical leadership, not people management)
• Maintaining legacy systems or handling internal IT infrastructure
  
  

Basic Requirements

Staff Software Engineer key responsibilities

• A minimum of 5 years of professional software development experience building software products
• A minimum of 3 years in a lead engineer role (conducting code reviews) or as an architect (driving key technical decisions)
• Experience developing platform-level products where other teams integrated with your APIs
• Active, deep engagement with AI tools, continuously 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-AE-Dubai-StaffSoftwareE.001