[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, and they are seeking a Senior AI Engineer to build internal tools and workflows that leverage AI across the organization. The role involves identifying high-leverage problems, developing prototypes, and integrating AI tools into business processes to enhance operational efficiency.

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

• A prolific builder with senior judgment
• Deep applied-AI fluency
• Systems-integration chops
• A pattern-setter and force multiplier
• A strong communicator
• Low ego, high agency

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 + All Whatnauts are expected to develop a deep understanding of our product. We're passionate about building the best user experience, and all employees are expected to use Whatnot as both a buyer and a seller as part of their job (our dogfooding budget makes this fun and easy!).
• Parental Leave + 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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