Technical Director, AI Programs

We’re looking for a Technical Director to provide senior technical leadership across a large, multi-stream agentic AI program. This is a leadership role, not a hands-on build role. You’ll lead through influence across internal, partner, and vendor teams, making sure every workstream is building the right thing, the right way, and solving the problem the client actually has.

In this role, you’ll provide delivery oversight across roughly ten concurrent workstreams and up to about a hundred people. You’ll validate that teams are on the right architectural path, connect their work back to client business outcomes, and step in early when something won’t land. You’ll act as the trusted technical voice with client leadership, working backwards from the outcomes the client is trying to achieve.

Why This Role Matters

At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate.

Every role here contributes directly to that mission. Here, you shape how AI systems integrate into enterprise operations, how teams move at real velocity, and how products create measurable impact for clients and the people they serve. We ship production-ready AI in 30 to 45 days. That pace demands people who take ownership, lead with craft, and care deeply about what they put their name on.

What You’ll Do

Delivery & Technical Oversight

Provide delivery oversight across all agentic AI workstreams, making sure each is on track to the outcomes committed to the client

Validate that each team is building the right solution architecturally, reviewing designs, diagrams, and tradeoffs closely enough to catch flaws early

Work backwards from the client’s business outcomes to test whether what’s being built will actually meet the need, and course correct well before a milestone or demo exposes a gap

Read between the lines of status updates: surface hidden risks, dependency gaps, and unspoken blockers, and push teams to name and resolve them

Join solutioning sessions, brainstorms, and client calls as needed to align direction, resolve ambiguity, and reset expectations

Set and uphold standards for how agentic systems are designed, evaluated, secured, and prepared for production, including multi-agent orchestration, tool calling, RAG, evaluation, observability, and guardrails

Stay close enough to the technology to go deep when it matters, using tools like Claude and Cursor to explore and pressure-test ideas

Collaboration & Communication

Serve as the senior technical voice to client leadership, translating between architecture detail and business outcomes

Lead across vendors, partner teams, and internal teams you don’t directly manage, building trust and alignment without relying on formal authority

Hold direct conversations when a team is sandbagging or guarded, with the EQ to probe, ask hard questions, and drive to a clear answer, live and in the room, not only in async channels

Partner with the engagement, product, and strategy leads who own scope and program management so technical direction and delivery stay in step

Co-define the AI roadmap with client and R&P leadership, operating as a peer in strategic technical conversations

Leadership & Influence

Act as the technical authority the whole program can rely on, owning high-stakes calls on architecture, risk, and delivery

Mentor technical leads across streams, raising the bar for how teams build and communicate

Define and champion the standards that shape how this program builds and operates agentic AI