Founding Head of Engineering

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take complete responsibility for the product's codebase, architecture, and roadmap.

• Lead engineering efforts for the AI-native product and manage technical direction from start to finish.

• Develop and integrate LLM-based generation, agentic workflows, evaluations, and production infrastructure.

• Deliver features from initial concepts to users, determining what to create, omit, or postpone.

• Make informed decisions regarding model selection, evaluation frameworks, data and inference pipelines, observability, latency, cost, and quality.

• Construct evaluation and observability layers for customer security, procurement, and legal teams.

• Engage in weekly customer calls and convert customer feedback into actionable product decisions.

• Recruit, interview, and hire the engineering team.

• Define and cultivate engineering culture, standards, review practices, failure management, and shipping cadence.

• Mentor future hires and establish benchmarks for code quality and delivery.

• Collaborate with product and leadership on strategy, prioritization, and customer feedback mechanisms.

⛳️ Requirements

• Experience leading engineering teams at scale while intentionally adopting a small, hands-on role.

• Background as a founding or early engineer at a venture-backed AI startup.

• Delivered agentic LLM systems to enterprise customers.

• Proven track record of making rewrite-versus-keep decisions on an existing codebase.

• Hired and mentored engineers and set a high technical standard in early-stage environments.

• Deliberately established an engineering culture that measurably enhanced team performance.

• Successfully navigated a regulated procurement gate in production, such as security reviews, bias audits, or compliance certifications.

• Full-stack proficiency across backend, frontend, and infrastructure.

• Capable of translating customer needs into technical specifications for the codebase.

• Strong communication skills with both technical and non-technical stakeholders.

• Proficient in Python.

• Familiarity with Temporal or similar workflow orchestration platforms.

• Production experience with major model providers like Anthropic or OpenAI, including migrations.

• Developed trusted customer-facing evaluations.

• Experience in delivering AI-native products within regulated industries.

• Contributions to open-source projects or technical writing in AI/ML.

• Cover letter must outline built projects, achievements, desired work, and the most challenging agentic-system decision made in the past year.

• Provide links to code, projects, or any released work.

🏝️ Benefits

• Remote work arrangement available throughout Canada.

• Opportunities for career advancement.

• A people-focused, multicultural, and diverse team environment.

• An inclusive and accessible recruitment process.

• Alternative assessment methods available upon request.

• Accommodation offered at any stage of the recruitment process.