AI Technical Lead

Technical Lead/Architect

Remote - United States

We're a small team within Blackboard building a new AI-native product. This is not a feature team, and it's not an enhancement to an existing product — we're building something new.

We use Claude Code, Cursor, and AI-assisted tooling to generate the majority of our code. Our engineers are architects, reviewers, and product thinkers — people who direct AI coding agents effectively rather than writing every line by hand.

As Technical Lead, you set this culture. You will establish the norms, the workflows, and the standards for how AI-native development actually works at scale on a small team. The person we're looking for is excited by this model, not threatened by it.

You are the technical leader. You will design, architect, and build the core system — a stateful, multi-layer architecture spanning data ingestion, decision logic, and AI-powered delivery — and recruit a small senior team to build alongside you.

This is a builder role first. If you're looking to step into a seat where you primarily direct others, this isn't the right fit. We need someone who still loves building — and is exceptional  will own the full technical vision and be accountable for it.

• A multi-layer system where each layer is decoupled, auditable, and independently evolvable
• A persistent learner state model built to reason across complex, longitudinal user data
• A rules-based decision layer where logic is explicit and transparent — every recommendation can be explained

• Event-driven pipelines that translate real-time platform activity into structured, reliable signals
• APIs that connect the intelligence layer to the user-facing product
• LMS integration for real-time data ingestion, designed to scale across platforms over time

• A multi-agent system backed by shared state — precision-bounded interventions, not open-ended AI responses
• Prompt engineering and guardrail systems that keep agent behavior auditable and aligned
• Observability infrastructure so every system decision can be monitored, debugged, and improved

• Establish an AI-native development culture: AI tools as the default, human judgment as the filter
• Weekly ship cycles, high observability, and a bias toward iteration over speculation
• Hire and mentor a small senior team (2–3 Product Engineers) as the product scales from v1 to v2
• Stay on the bleeding edge of the AI ecosystem — Claude Code, Cursor, OpenAI Agent SDK, MCPs, and whatever comes next. Make the call on what we adopt, when, and why. That judgment sets the standard for the whole team.

You believe that intelligence should be deterministic where it can be, and generative where it should be. You're skeptical of LLMs as decision-makers but excited about them as expression engines. You've seen what happens when AI systems are unauditable — and you've built against that failure mode.

You're energized by constraints: small team, big surface area, real stakes. You move fast, accept imperfection in v1, and know that iteration is how great systems are built. You want the work to matter.

You think in systems, not screens. You hold strong opinions, loosely held — and you care more about impact than credit.

Please include a link to your portfolio/Git Hub as part of your application.

• Proven track record shipping complex, stateful AI or data-driven systems in production — not just prototypes
• Fluency in LLM application development: orchestration, RAG pipelines, prompt engineering, guardrail design
• Experience designing multi-agent systems with shared state, async architectures, and observability infrastructure
• Strong architectural judgment — you understand why rules should decide and AI should assist, and you build accordingly
• Demonstrated ability to ship at startup velocity: high ownership, weekly cycles, bias toward action
• You work natively with AI coding tools (Cursor, Claude Code, or equivalent) — this is how you actually build, not a checkbox
• Experience recruiting and mentoring engineers
• Fluency in written and spoken English