Lead Software Engineer, .AI; Remote

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

Lead Software Engineer, Learn With.

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

Join to apply for the Lead Software Engineer, Learn With.

AI (Remote) - $200,000/year USD role at Crossover
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Base pay range

$100.00/hr - $100.00/hr

Platform Overview

We’re operating platforms that support thousands of students and distributed teams:

• Time Back:
  Educational platform driving Alpha School’s 2‑hour learning model (99th percentile test results).
• Incept:
  Content generation platform producing all personalized educational content for multiple learning applications deployed at Alpha School.
• Crossover: AI‑powered hiring platform handling tens of thousands of applicants per month, staffing schools and companies globally.

You’ll take ownership of one of these platforms and dedicate most of your time to building the intricate components of the codebase with a small team (3‑5 senior engineers, no junior members). Your architectural choices dictate whether other teams can quickly build new applications, integrate seamlessly, and deliver value to students. Execute this well and you unlock significant leverage. Poor decisions generate integration chaos and eliminate velocity across multiple teams.

What

You Will Be Doing

• Technical Leadership:
  Drive strategic architectural decisions and define technical patterns for the team to adopt.
• AI Leadership:
  Advance adoption of emerging AI workflows and develop high‑impact playbooks.
• Implementation:
  Construct the complex, mission‑critical components of the codebase with your team.
• Quality Reviews:
  Verify your team adheres to established patterns and upholds quality standards.

What You Won’t Be Doing

• Serving as an architect without coding
• Spending time in endless meetings
• Managing people (this is a technical leadership position, not a people management role)
• Maintaining legacy systems or internal IT infrastructure

Basic Requirements

• At least 5 years of professional software development experience building software products
• At least 3 years as either a lead engineer (reviewing others’ work) or architect (making key technical decisions)
• Experience working on 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 leans on 50+ years of learning science, cutting‑edge data analytics, and AI‑powered coaching. In doing so, we 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 on this topic.

Seniority

level

Mid‑Senior level

Employment type

Full‑time

Job function

Business Development, Engineering, and Information Technology

Industries

Software Development, IT Services and IT Consulting, and Technology, Information and Internet

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