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

Lead Software Architect, LearnWith.AI (Remote) - $200,000 / year USD Join to apply for the

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

role at

Crossover .

This role is a fully remote, full‑time position operating as an independent contractor through Crossover. Compensation is $100 / hr, equivalent to $200,000 / year.

Base Pay Range $100.00 / hr - $100.00 / hr

Platforms We’re operating platforms that serve thousands of students and teams in production :

TimeBack : Educational platform supporting 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 will take ownership of one of these platforms and dedicate most of your time to implementing the technically demanding components of the codebase with a small team (3‑5 strong engineers, no juniors). Your architectural choices dictate whether other teams can ship new applications quickly, integrate seamlessly, and deliver value to students. Effective decisions unlock massive leverage; poor choices create integration chaos and slow down multiple teams.

You design what you build and operate. You define quality standards and technical patterns for your platform. We follow a spec‑driven approach : you architect before you code, always design before you execute. High autonomy, no committees, no approval boards. Small, cohesive team where you’re accountable for what you deliver.

What You Will Be Doing

Technical Leadership : Make strategic architectural choices and define technical patterns for the team to adopt.

AI Leadership : Champion the adoption of new AI workflows and develop high‑impact playbooks.

Implementation : Build the complex, mission‑critical components of the codebase alongside your team.

Quality Reviews : Verify your team adheres to established patterns and upholds quality standards.

What You Won’t Be Doing

Functioning as an architect without writing code.

Spending time in endless meetings.

Managing people (this is a technical leadership position, not a people‑management role).

Working on legacy maintenance 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 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 draws 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—while having fun.

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 payment period is weekly.

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