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.

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

Skills

• Proficient in building internal tools, prototypes, and business workflows that utilize AI
• Experience in shipping a high volume of apps and prototypes quickly
• Ability to define reusable patterns and shared infrastructure for the organization
• Experience embedding AI into real business contexts with appropriate PII and access controls
• Skilled in integrating AI tools with internal systems and data sources via APIs, connectors, and event-driven workflows
• Ability to evaluate and bring in new models, tools, and patterns as the AI ecosystem evolves
• Extensive hands-on experience with current generation LLM products (Anthropic, OpenAI, Google) and production patterns
• Experience in systems integration, connecting AI to real data and tools through APIs, webhooks, and connectors
• Strong communication skills to translate non-technical user problems into software solutions
• Ability to mentor other engineers and raise the technical bar for the organization

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
• Monthly allowance for wellness
• Annual allowance towards Childcare
• Lifetime benefit for family planning, such as adoption or fertility expenses
• 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.

Company Overview

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