Lead Software Engineer, AI

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

📋 Description

• Develop the technical strategy and architecture for AI-driven product experiences within the learner and content-authoring ecosystem.

• Create, construct, and deploy full-stack systems utilizing TypeScript, Vue.js, Node.js, PostgreSQL, and Azure.

• Lead intricate, cross-functional projects from problem identification through to delivery, adoption, and ongoing enhancement.

• Establish reusable frameworks for retrieval-augmented generation, agentic workflows, model orchestration, prompt management, and human-in-the-loop experiences.

• Design and uphold evaluation frameworks, quality metrics, observability, and feedback loops for features powered by LLM.

• Integrate APIs from Anthropic, OpenAI, and other models while considering reliability, latency, token usage, cost, privacy, security, prompt-injection risk, and graceful degradation.

• Direct the technical trajectory for AI-enhanced content authoring and management functionalities.

• Collaborate with product, platform, design, data, and engineering teams to convert ambiguous challenges into technical plans and deployable systems.

• Identify architectural risks, elucidate tradeoffs, and balance speed, quality, maintainability, and long-term leverage.

• Elevate engineering standards through design reviews, code reviews, technical documentation, operational standards, and development practices.

• Mentor and nurture engineers in AI-assisted development, context engineering, evaluation design, system reliability, and agentic workflows.

• Utilize agentic coding tools such as Claude Code, Cursor, or similar for planning, implementation, testing, and review.

• Ensure systems are scalable, observable, secure, accessible, and economically viable in production.

• Participate in engineering-wide discussions regarding responsible AI adoption, technical standards, platform capabilities, and organizational priorities.

⛳️ Requirements

• Over 10 years of experience in building and operating customer-facing software products.

• Proven impact as a technical leader, staff engineer, principal engineer, tech lead, or in a comparable role.

• Strong foundational knowledge in full-stack engineering, including browser technologies, TypeScript, Node.js, PostgreSQL, cloud infrastructure, and distributed systems.

• Experience in designing and delivering AI-driven products utilizing LLMs, retrieval systems, evaluation frameworks, agentic workflows, or similar technologies.

• A history of leading complex initiatives that cross multiple teams, systems, or organizational boundaries.

• Capability to set technical direction without formal authority and foster alignment among stakeholders.

• Strong architectural judgment with the ability to articulate complex tradeoffs clearly to both technical and non-technical audiences.

• Experience in creating sustainable engineering patterns, platforms, or capabilities.

• A product-oriented mindset with a focus on user experience, quality, speed, and measurable outcomes.

• Comfort in navigating ambiguous environments.

• High ownership mentality across strategy, architecture, implementation, and operational follow-through.

• Experience in mentoring engineers and enhancing engineering practices.

• Commitment to reliable, secure, observable, and cost-effective AI systems.

• Ability to thrive in a remote, asynchronous-first work environment.

• Experience in a startup or organization with a high engineering standard.

• Must reside in and perform work within the United States.

• Willingness and ability to travel as necessary.

• Employees are expected to be on camera during meetings unless there are extenuating circumstances.

• Successful completion of applicable pre-employment screening requirements.

• Completion of employment eligibility verification via Form I-9.

🏝️ Benefits

• Medical insurance.

• Dental insurance.

• Vision insurance.

• Flexible spending accounts.

• Generous paid time off.

• Sponsored volunteer opportunities.

• 401(k) plan with a company match.

• Complimentary access to all Penn Foster Group online programs.

• Remote work arrangement.

• Occasional travel for team meetings, company events, conferences, and summits.