About the Position

Technical Director, AI Programs

CA Remote

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.

Responsibilities

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
Drive the technical vision for the program as it scales, shaping how the work grows over the long term

Requirements

15+ years in engineering, data, or AI, with a career that began as an engineer and moved into leading large programs
Experience overseeing large, multi-team programs, ideally as a director or senior director who came up through engineering; a principal-level product or technical architect who operated as the right hand to a VP or SVP is also a strong fit
A history of being held accountable for business outcomes, not just technical delivery
Technical depth kept sharp: you can go deep architecturally, diagram a system, weigh tradeoffs, and call out a weak design. You don’t need to be committing code daily
Recent, real exposure to agentic AI, including agentic platforms or builds, multi-agent orchestration, tool calling, RAG, and evaluation
Strong judgment in spotting when a team is solving the wrong problem or a solution won’t meet the client’s need
Exceptional communication and EQ, including credibility with senior executives and comfort with conflict and hard conversations
Experience working across multiple vendors, partners, or organizations to align on shared outcomes
Experience in a regulated industry such as healthcare, life sciences, banking, insurance, or EdTech, including compliance regimes like SOC 2, ISO, or FERPA. Life sciences domain expertise is not required
Working knowledge of AWS and the AWS GenAI offering (e.g., Amazon Bedrock) and other major cloud platforms
Based in the US or Canada, with solid overlap with US Eastern or Central working hours

Nice to Have

Experience in both product and services environments, with a clear line from business strategy to delivered outcomes
A data science or ML background that lets you engage credibly with model and evaluation decisions
Prior experience working alongside AWS teams or on AWS-partnered engagements

We Offer

Competitive salary
Opportunity to work in a dynamic and innovative environment
Collaborative and inclusive company culture
Professional growth and development opportunities

Technical Director, AI Programs

Job description