Lead Software Architect, .AI; Remote

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

Overview

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

• Time Back:

An educational platform driving Alpha School's 2-hour learning model (99th percentile test results).

• Incept: A content generation platform producing all personalized educational content for multiple learning applications deployed at Alpha School.
• Crossover:

An AI-powered hiring platform processing tens of thousands of applicants monthly, staffing schools and companies worldwide. You will take ownership of one platform and dedicate the majority of your time to building its most complex components with a small team (3-5 senior engineers, no juniors). The architectural choices you make determine whether other teams can build new applications quickly, integrate smoothly, and deliver value to students. Strong decisions unlock massive leverage. Poor decisions generate integration failures and destroy velocity across multiple teams. You design, build, and operate your systems. You define quality standards and establish patterns for your platform. We operate on a spec-driven model: you design before implementing, always planning before building. Expect high autonomy, no committees, no review boards. You work within a small, focused team where accountability for what you ship is direct. What You Will Be Doing

• Technical Leadership:

Drive strategic architectural decisions and define technical patterns the team will follow.

• AI Leadership:

Champion the 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 that your team adheres to established patterns and upholds quality standards. What You Won’t Be Doing

• Acting as an architect without hands-on implementation
• Being trapped in continuous meetings
• Managing people (this role is technical leadership, not people management)
• Maintaining legacy systems or supporting internal IT infrastructure

Basic Requirements

• A minimum of 5 years of professional software development experience building software products
• A minimum of 3 years serving as either a lead engineer (reviewing others work) or architect (making key technical decisions)
• Experience delivering 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. Crossover Job Code: LJ-5106-CA-Toronto-Lead Software Ar . 002 #J-18808-Ljbffr Apply tot his job Apply To this Job