Senior Software Engineer, AI Experience

Job description

Position Summary: As a Senior Software Engineer, AI Experience at Pen***, you will build AI-native products end-to-end — owning features that shape how millions of learners discover, enroll in, and progress through our programs. This is a hands-on full-stack role for an engineer who treats LLMs as core product infrastructure, designing retrieval pipelines, building agentic workflows, writing evals, and pushing features from prototype to production. You will collaborate closely with product, platform, and other engineering teams, mentor peers on agentic development practices, and help set the bar for what good looks like in an AI-first engineering org. This position is fully remote. Essential Job Functions: • Design, build, and ship full-stack features end-to-end using TypeScript, Vue.js, and Node, deployed on Azure. • Write evals and observability for LLM features. • Use agentic coding tools (Claude Code, Cursor, or equivalent) as your primary development environment for planning, executing, and reviewing AI-generated work to ship faster while maintaining clean code that is ready for change. • Take ownership of AI-powered content authoring and management features. • Integrate model APIs (Anthropic, OpenAI, others) with attention to tokenization, latency, cost control, prompt-injection risk, and graceful degradation when models fail. • Collaborate closely with product, platform, and sibling engineering teams to translate ambiguous problems into shippable systems. • Lead code reviews, set technical standards for AI-assisted development, and mentor engineers on prompting, context engineering, eval design, and agentic workflows. • Ensure scalability, security, observability, and unit economics of the systems you own. Knowledge, Skills, Abilities: • 5+ years of experience building customer-facing products at a high-quality software company. • Strong UI and TypeScript fundamentals, with experience across the full stack (Browser technologies, Node, PostgreSQL). • Track record of driving complex, end-to-end features (not just incremental improvements and refactors) with visible impact on the product. • Product sensibility: you care about UX, speed, and polish, and you push back when something doesn't feel right. • Comfortable working without heavy PM overhead; you can help to shape the problem, not just implement a solution. • High ownership mentality: self-directed, full-lifecycle builder who takes a feature from idea to shipped. • Thrives in a remote, async-first environment with a lean, high-output team. • Experience at a startup or a company with a genuinely high engineering bar. 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, etc. 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 Pen*** 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 Pen***, 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 them to achieve long-term success in the workplaces of the future. Our history dates back to 1890 when our founder, Thomas Foster, pioneered distance education by offering training by mail for coal miners to get the necessary skills for safer jobs. Today, with the partners who use our education and training programs, we continue that mission of providing accessible training and education for in-demand skills and are building a workforce that’s prepared for the future job market. Equal Employment Opportunity: We strive toward Diversity, Equity, and Inclusion at Pen*** by intentionally building teams that are diverse – in identities, lived experiences, and ideas to create a culture where people feel connected to each other and have a sense of belonging. We value diversity, equity, and inclusion because it is the foundation that enables us to achieve what we set out to do as an organization – from maximizing the number of learners who can reach their goals while giving them the kinds of experiences we want them to have, to becoming the type 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 401K with a company match, plus free access to all of our online programs.