AI Tooling Engineer

Whatnot•Los Angeles, CA

1d•$200,000 - $260,000•Remote

About The Position

Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops. As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact. We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce.

Requirements

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 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
Low ego, high agency—you see inefficiency, build the fix, and bring people along with you

Responsibilities

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 and shared infrastructure the org builds on—reference architectures, internal libraries, MCP servers, eval harnesses, and templates that let others move faster and safer
Embed directly with teams across CX, Trust & Safety, ops, GTM, and EPD to find high-leverage problems, then build the solution alongside them
Wire 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 controls
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 making the build-vs-buy calls

Benefits

Flexible Time off Policy and Company-wide Holidays (including a spring and winter break)
Health Insurance options including Medical, Dental, Vision
Work From Home Support
Home office setup allowance
Monthly allowance for cell phone and internet
Care benefits
Monthly allowance for wellness
Annual allowance towards Childcare
Lifetime benefit for family planning, such as adoption or fertility expenses
Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally
Monthly allowance to dogfood the app
16 weeks of paid parental leave + one month gradual return to work company leave allowances run concurrently with country leave requirements which take precedence.