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.

• You'll partner with Whatnot’s AI Platform and Developer Tools teams to leverage their systems, add new functionality, and find ways to accelerate adoption by non-technical team members.
• This is a high-velocity, high-judgment builder role. You've shipped a lot of apps and prototypes—you're someone who can sit with a CX lead or an ops manager, understand their workflow in an afternoon, and have a working prototype in their hands by the end of the week.
• You create leverage for yourself by building on top of 3rd party tools where it’s advantageous but also know how to navigate lower-level interfaces where necessary.
• You also operate above any single project: you help decide where the opportunities are, define the reusable patterns and infrastructure others adopt, and raise the bar for how the whole company builds with AI.
• You move fluidly across the stack (frontend, backend, data, and the AI layer) and are deeply fluent in the current generation of AI tools and the production patterns around them—prompt engineering, RAG, MCP, agents, and evals.
• This is not a model-training or research role. You won't be training models—you'll be building the tools, workflows, and integrations that make off-the-shelf AI dependable and useful inside Whatnot's systems and processes.

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

Benefits

• Generous Holiday and Time off Policy
• 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
• Retailer; 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

EEO

We are proud to be an Equal Opportunity Employer. We value diversity, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, parental status, disability status, or any other status protected by local law. We believe that our work is better and our company culture is improved when we encourage, support, and respect the different skills and experiences represented within our workforce.