Sr. Director of Engineering

SENIOR DIRECTOR, PRODUCT ENGINEERING

Build AI that clinicians and educators can trust.

A builder‑leader role for someone who can move from architecture to prototype to production in a high‑trust, mission‑driven domain.

VP of Product, Design, & Engineering

Remote / Hybrid; occasional in‑person

Minimal

$250K-$280K base + bonus

Every year, clinicians and educators rely on WPS to support children with autism, learning differences, and developmental needs. We are building the next generation of tools for high‑stakes assessment work – tools that are rigorous, humane, reliable, and ready for responsible AI.

We are hiring a Senior Director of Product Engineering to help lead that transformation. You will set product engineering architecture, lead applied AI development, build the technical foundation for safe AI features, and ship customer‑facing capabilities that make practitioners faster, more precise, and more confident.

Real ownership

Visible authority over architecture, technical standards, and applied AI direction.

Meaningful impact

Build tools that support clinicians, educators, children, families, and care teams.

Careful AI

Join a culture that values judgment, evidence, privacy, safety, and trust over AI hype.

• Own product engineering architecture: modernize what slows the business down and ship what moves customers forward.
• Build the WPS AI foundation: permissions‑aware content retrieval, evaluation harnesses, telemetry, audit logs, and feedback loops.
• Design, prototype, and ship AI/LLM‑powered capabilities, including RAG pipelines, agent workflows, and evaluation frameworks.
• Set technical strategy alongside Product, Design, Clinical, Research, and Sales stakeholders.
• Establish standards for cloud architecture, CI/CD, observability, model governance, privacy, safety, and accessibility.
• Define metrics that matter: system reliability, delivery velocity, model quality, adoption, and practitioner trust.
• Mentor engineers and build a culture where technical excellence and shipping velocity are both expected.

• 10+ years in software engineering, including meaningful architecture and product delivery ownership.
• 3+ years leading engineers, with evidence that you can still go deep technically.
• Production software experience in a high‑accuracy, high‑trust, or regulated environment.
• Hands‑on experience shipping or evaluating LLM‑powered features, RAG systems, agent workflows, or AI‑enabled product surfaces.
• Experience modernizing an existing product or platform while continuing to ship customer value.
• Strong cross‑functional judgment with Product, Design, domain experts, and non‑technical executives.

• Clinical, education, assessments, healthcare, publishing, or expert‑content domain experience.
• Built or led an applied AI engineering team.
• Experience with model governance, MLOps, evals, safety guardrails, and auditability.
• Cloud‑native systems architecture across AWS, GCP, or Azure; distributed systems, APIs, and data platforms.
• A track record of moving quickly and responsibly in ambiguous environments.
• Curiosity about emerging technologies without being locked into a single tool, stack, or preference.

• Owning the path from architecture to prototype to production.
• Building high‑performing teams while staying close to the work.
• Using AI thoughtfully to increase leverage, not replace judgment.
• Partnering with Product to translate customer problems into technical solutions.

• You prefer strategy decks to shipped systems, evals, user feedback, and production tradeoffs.
• You want to manage managers from a distance and avoid hands‑on technical work.
• You are casual about clinical accuracy,…