[Remote] AI Tooling Engineer

Note: The job is a remote job and is open to candidates in USA. Whatnot is the largest livestream shopping platform in North America and Europe, enabling users to buy, sell, and discover various products. The Senior AI Tooling Engineer will build internal tools and workflows to integrate AI into the company's operations, driving impactful solutions across multiple teams.ResponsibilitiesOwn ambiguous, cross-org AI bets end-to-end—identify the highest-leverage problems across the company, decide what to build, and drive it from prototype to durable production toolBuild and ship a high volume of internal apps, prototypes, and automations—going from a vague problem to a working tool in days, then iterating with users toward production qualityDefine the reusable patterns and shared infrastructure the org builds on—reference architectures, internal libraries, MCP servers, eval harnesses, and templates that let others move faster and saferEmbed directly with teams across CX, Trust & Safety, ops, GTM, and EPD to find high-leverage problems, then build the solution alongside themWire AI into real business context—building RAG and retrieval pipelines, MCP servers, and agentic workflows grounded in Whatnot's data, with appropriate PII and access controlsIntegrate AI tools with internal systems and data sources via APIs, connectors, and event-driven workflows so automations act on real state, not toy inputsScale the leverage—package successful builds into reusable skills and playbooks, and level up the whole company through enablement sessions, boot camps, and mentorship of other buildersStay ahead of the AI landscape, evaluating and bringing in new models, tools, and patterns as the ecosystem evolves, and making the build-vs-buy callsSkillsProficient in building internal tools, prototypes, and business workflows that utilize AIExperience in shipping a high volume of apps and prototypes quicklyAbility to define reusable patterns and shared infrastructure for the organizationExperience embedding AI into real business contexts with appropriate PII and access controlsSkilled in integrating AI tools with internal systems and data sources via APIs, connectors, and event-driven workflowsAbility to evaluate and bring in new models, tools, and patterns as the AI ecosystem evolvesExtensive hands-on experience with current generation LLM products (Anthropic, OpenAI, Google) and production patternsExperience in systems integration, connecting AI to real data and tools through APIs, webhooks, and connectorsStrong communication skills to translate non-technical user problems into software solutionsAbility to mentor other engineers and raise the technical bar for the organizationBenefitsFlexible Time off Policy and Company-wide Holidays (including a spring and winter break)Health Insurance options including Medical, Dental, VisionWork From Home SupportHome office setup allowanceMonthly allowance for cell phone and internetMonthly allowance for wellnessAnnual allowance towards ChildcareLifetime benefit for family planning, such as adoption or fertility expenses401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationallyMonthly allowance to dogfood the app16 weeks of paid parental leave + one month gradual return to work \•company leave allowances run concurrently with country leave requirements which take precedence.Company OverviewWhatnot is a livestream shopping platform for buying and selling products. It was founded in 2019, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is https://www.whatnot.com.Company H1B SponsorshipWhatnot has a track record of offering H1B sponsorships, with 6 in 2026, 34 in 2025, 20 in 2024, 18 in 2023, 10 in 2022. Please note that this does not guarantee sponsorship for this specific role.