AI Tooling Engineer

The Role

We're looking for an AI Engineer to build the internal tools, prototypes, and business workflows that put AI into the hands of every team at Whatnot. You'll own ambiguous, cross-org bets end-to-end: finding real problems, shipping working software fast, hardening what works, and scaling how Whatnot gets value out of AI.

• Own 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 tool
• Build 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 quality
• Define the reusable patterns the org builds on, including reference architectures, internal libraries, MCPs, and skills/plugins that let others move faster and safer
• Embed directly with teams across CX, Trust & Safety, Ops, and GTM to find high-leverage problems, then build the solution alongside them
• Integrate AI tools with internal systems and data sources via APIs, connectors, and event-driven workflows so automations act on real state, not toy inputs
• Scale 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 builders
• Stay ahead of the AI landscape, evaluating and bringing in new models, tools, and patterns as the ecosystem evolves, and make the build-vs-buy calls

Who You Are

• A prolific builder with senior judgment—you ship fast and iterate with real users, and you know where not to invest; you measure yourself by problems solved, tools adopted, and leverage created
• Deep applied-AI fluency—extensive hands-on experience building with the current generation of LLM products (Anthropic, OpenAI, Google) and popular agent frameworks (Cowork, Glean, Dust, etc) and the production patterns around them: prompt engineering, RAG, MCP, agents, and evals
• Systems-integration chops—you've connected AI to real data and tools through APIs, webhooks, and connectors, and you reason rigorously about reliability, latency, cost, and access controls
• A pattern-setter and force multiplier—you've defined how teams build, mentored other engineers, and raised the technical bar for an org, not just your own output
• A strong communicator—you can sit with non-technical users, translate their problems into software, and teach them to build for themselves
• A low ego, high agency—you see inefficiency, build the fix, and bring people along with you