Technical Director (AI Programs)

Location: Remote; must be based in the US or Canada with solid overlap with US Eastern or Central working hours.

Salary: $207,000–$306,630 USD; budget is approximately $275,000 USD.

Company

Robots & Pencils designs and delivers production-ready AI systems that integrate into enterprise operations and real-world workflows.

What you will do

• Provide delivery and technical oversight across roughly ten concurrent agentic AI workstreams involving up to about 100 people.
• Review architectures, designs, diagrams, tradeoffs, dependencies, risks, and blockers, correcting direction before milestones or demos.
• Set and uphold standards for agentic system design, evaluation, security, production readiness, multi-agent orchestration, tool calling, RAG, observability, and guardrails.
• Translate architecture into client business outcomes and serve as the senior technical voice with client leadership.
• Lead internal, partner, and vendor teams through influence, alignment, difficult conversations, and strategic roadmap development.
• Own high-stakes architecture, risk, and delivery decisions; mentor technical leads and shape the program’s long-term technical vision.

Requirements

• 15+ years in engineering, data, or AI, with a career that began as an engineer and progressed into leadership of large programs.
• Experience overseeing large, multi-team programs, ideally as a director or senior director from an engineering background; principal-level product or technical architects who acted as a right hand to a VP or SVP are also considered.
• Track record of accountability for business outcomes, not only technical delivery.
• Strong architectural depth, including diagramming systems, weighing tradeoffs, identifying weak designs, and reviewing technical direction without needing to code daily.
• Recent, practical agentic AI experience, including agentic platforms or builds, multi-agent orchestration, tool calling, RAG, and evaluation.
• Strong judgment in identifying incorrect problem framing or solutions that will not meet client needs.
• Exceptional communication and emotional intelligence, including executive credibility and comfort with conflict and difficult conversations.
• Experience aligning multiple vendors, partners, or organizations around shared outcomes.
• Experience in a regulated industry such as healthcare, life sciences, banking, insurance, or EdTech, including compliance regimes such as SOC 2, ISO, or FERPA.
• Working knowledge of AWS, Amazon Bedrock or other AWS GenAI offerings, and other major cloud platforms.
• Must be based in the US or Canada and overlap with US Eastern or Central working hours.

Nice to have

• Experience in both product and services environments, connecting business strategy to delivered outcomes.
• Data science or machine learning experience enabling credible participation in model and evaluation decisions.
• Experience working alongside AWS teams or on AWS-partnered engagements.

Culture & Benefits

• Leadership through ownership, direct feedback, clear commitments, and accountability.
• Fast-paced delivery environment focused on shipping production-ready AI in 30–45 days.
• Work alongside experienced teams averaging more than fifteen years of experience.
• Expect hands-on technical engagement when needed, including using tools such as Claude and Cursor to pressure-test ideas, without daily coding being required.