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Software Engineer, .AI; Remote

Remote / Online - Candidates ideally in
Singapore
Listing for: Crossover
Full Time, Remote/Work from Home position
Listed on 2026-01-23
Job specializations:
  • Software Development
    AI Engineer, Software Engineer
Salary/Wage Range or Industry Benchmark: 200000 SGD Yearly SGD 200000.00 YEAR
Job Description & How to Apply Below
Position: Staff Software Engineer, LearnWith.AI (Remote) - $200,000/year USD

We operate platforms that serve thousands of students and teams at scale:

  • Time Back:
    An educational platform that drives Alpha School's 2-hour learning model (achieving 99th percentile test scores).
  • Incept: A content generation platform producing all personalized educational materials for multiple learning applications deployed at Alpha School.
  • Crossover:
    An AI-driven hiring platform that processes tens of thousands of applicants monthly, staffing schools and organizations worldwide.

You will take ownership of one of these platforms and dedicate most of your time to building the most complex components of the codebase with a small team (3-5 experienced engineers, no junior developers). The architectural choices you make will determine whether other teams can build new applications quickly, integrate seamlessly, and deliver value to students. Correct decisions unlock massive leverage.

Poor decisions create integration failures and slow down multiple teams.

You design, build, and operate what you create. You set the quality standards and establish patterns for your platform. We follow a spec-driven approach: design precedes implementation, planning comes before building. High autonomy is standard, with no committees or review boards. You work in a small, cohesive team where you are accountable for what you deliver.

What You Will Be Doing
  • Technical Leadership:
    Define strategic architectural decisions and set technical patterns for the team to adopt.
  • AI Leadership:
    Champion the adoption of emerging AI workflows and develop high-impact playbooks.
  • Implementation:
    Construct the complex, mission-critical portions of the codebase working alongside 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 endless 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
  • At least 5 years of professional software development experience building software products
  • At least 3 years serving as either a lead engineer (reviewing others' work) or architect (making key technical decisions)
  • Experience developing platform-level products where other teams consumed your APIs
  • Deep engagement with AI tools, actively experimenting and pushing boundaries
About Learn With.

AI

Learn With.

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.

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