Lead Software Engineer, AI

Lead Software Engineer, AI ExperiencePenn Foster Group | Fully remote within the United StatesPosition Summary As a Lead Software Engineer, AI Experience at Penn Foster Group, you will provide technical leadership for the design and delivery of AI-native products that help millions of learners discover, enroll in, and progress through our programs.You will operate across product, engineering, and platform boundaries—turning ambiguous opportunities into reliable, scalable systems and establishing the technical direction for AI experiences across the organization. This is a hands-on role requiring strong full-stack execution, architectural judgment, and the ability to influence through technical strategy, design, and mentorship.You will help define how Penn Foster builds with AI by developing retrieval pipelines, agentic workflows, evaluation systems, and production-grade model integrations. You will partner with engineering leaders and product teams to identify high-leverage opportunities, shape technical roadmaps, raise engineering standards, and guide initiatives from early exploration through production adoption.Essential Job Functions

Define technical strategy and architecture for AI-powered product experiences across the learner and content-authoring ecosystem.
Design, build, and ship full-stack systems using TypeScript, Vue.js, Node.js, PostgreSQL, and Azure.
Lead complex, cross-functional initiatives from problem definition through delivery, adoption, and ongoing improvement.
Establish reusable patterns for retrieval-augmented generation, agentic workflows, model orchestration, prompt management, and human-in-the-loop experiences.
Design and maintain evaluation frameworks, quality metrics, observability, and feedback loops for LLM-powered features.
Integrate model APIs from Anthropic, OpenAI, and other providers with careful attention to reliability, latency, token usage, cost, privacy, security, prompt-injection risk, and graceful degradation.
Own technical direction for AI-powered content authoring and management capabilities.
Partner with product, platform, design, data, and sibling engineering teams to translate ambiguous problems into coherent technical plans and shippable systems.
Identify architectural risks, clarify tradeoffs, and make decisions that balance speed, quality, maintainability, and long-term leverage.
Raise the engineering bar through design reviews, code reviews, technical documentation, operational standards, and effective development practices.
Mentor and develop engineers across teams, particularly in AI-assisted development, context engineering, evaluation design, system reliability, and agentic workflows.
Use agentic coding tools such as Claude Code, Cursor, or equivalent to accelerate planning, implementation, testing, and review while maintaining strong standards for correctness, security, and maintainability.
Ensure that systems are scalable, observable, secure, accessible, and economically sustainable in production.
Contribute to engineering-wide discussions about responsible AI adoption, technical standards, platform capabilities, and organizational priorities.

Knowledge, Skills, and Abilities

10+ years of experience building and operating customer-facing software products.
Demonstrated impact as a technical leader, staff engineer, principal engineer, tech lead, or equivalent role.
Strong full-stack engineering fundamentals, including browser technologies, TypeScript, Node.js, PostgreSQL, cloud infrastructure, and distributed systems.
Experience designing and delivering AI-powered products using LLMs, retrieval systems, evaluation frameworks, agentic workflows, or related technologies.
A track record of leading complex initiatives that span multiple teams, systems, or organizational boundaries.
Ability to set technical direction without relying on formal authority and to build alignment among engineers, product leaders, designers, and other stakeholders.
Strong architectural judgment and the ability to communicate complex tradeoffs clearly to both technical and non-technical audiences.
Experience creating durable engineering patterns, platforms, or capabilities that enable other teams to move faster.
Product sensibility and a strong focus on user experience, quality, speed, and measurable outcomes.
Comfort working in ambiguous environments where the problem, solution, and path to execution must be shaped collaboratively.
High ownership mentality, with the ability to move between strategy, architecture, implementation, and operational follow-through.
Experience mentoring engineers and strengthening engineering practices across a team or organization.
Commitment to building reliable, secure, observable, and cost-effective AI systems.
Thrives in a remote, async-first environment with a lean, high-output team.
Experience working at a startup or organization with a high engineering bar and a bias toward meaningful, measurable impact.

Working Conditions & Hiring Process

U.S. Work Location Requirement: All employees must reside in and perform work within the United States. We do not support international remote work arrangements for this role.
Travel Expectations: While this is a remote position, occasional travel may be required for team meetings, company events, conferences, summits, and similar activities. Candidates must be willing and able to travel as needed.
On-Camera Work Environment: We operate in a highly collaborative, remote, on-camera culture. Employees are expected to be on camera during meetings unless extenuating circumstances apply.
Recorded Video Interviews: All video interviews conducted during the hiring process will be recorded to support internal hiring consistency and process improvement.
Background Checks: Employment with Penn Foster Group is contingent upon successfully completing applicable pre-employment screening requirements, which may include verification of employment history, education, and criminal background, where permitted by law.
Identity Verification (Form I-9): As part of our onboarding process, all hires must complete employment eligibility verification in compliance with federal law. This includes remote Form I-9 verification, which may require an in-person identity verification step with an authorized representative.

About Us At Penn Foster Group, we are transforming online learning to help learners by uniting Penn Foster, CareerStep, Ashworth College, James Madison High School, the New York Institute of Photography, the New York Institute of Art and Design, and other education platforms. Together, we create an accelerated path to greater economic mobility through real-world skills and knowledge that enable learners to achieve long-term success.Our history dates back to 1890, when our founder, Thomas Foster, pioneered distance education by offering training by mail for coal miners to gain the skills needed for safer jobs. Today, with the partners who use our education and training programs, we continue that mission by providing accessible training and education for in-demand skills and building a workforce prepared for the future job market.Equal Employment Opportunity We strive toward Diversity, Equity, and Inclusion at Penn Foster Group by intentionally building teams that are diverse in identities, lived experiences, and ideas, creating a culture where people feel connected to each other and have a sense of belonging. We value diversity, equity, and inclusion because they enable us to maximize the number of learners who reach their goals, deliver the experiences we want them to have, and become the kind of company we want to work in.What We Offer We offer a robust benefits package that includes medical, dental, vision, flexible spending, generous paid time off, sponsored volunteer opportunities, a 401(k) with a company match, and free access to all of our online programs.