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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 2026-01-10
Job specializations:
  • Software Development
    Software Engineer, AI 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

Staff Software Engineer, Learn With.

AI (Remote) - $200,000/year USD

Location:

Remote. Posted by Crossover.

Base pay range: $100.00/hr – $100.00/hr (equivalent to $200,000/year).

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

You will take ownership of one of these platforms and dedicate the majority of your time to constructing the most complex portions of the codebase with a compact team (3–5 accomplished engineers, no junior contributors). 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 generate integration failures and erode velocity across multiple teams.

You design, build, and operate your systems. You define quality standards and establish patterns for your platform. We follow a spec‑driven approach: design precedes implementation, planning comes before building. High autonomy, no committees, no approval boards. 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 high‑value playbooks.
  • Implementation:
    Construct the complex, critical components of the codebase working directly with your team.
  • Quality Reviews:
    Verify that your team adheres to established patterns and upholds quality benchmarks.
What You Won’t Be Doing
  • Serving as an architect detached from implementation.
  • Spending excessive time in meetings.
  • Managing personnel (this role focuses on technical leadership, not people management).
  • Maintaining legacy systems or handling internal IT infrastructure.
Key Responsibilities / Basic Requirements
  • A minimum of 5 years of professional software development experience delivering 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 other teams integrated with your APIs.
  • Strong engagement with AI tools, consistently experimenting and exploring new capabilities.
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.

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.

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