[Remote] AI Tooling Engineer

Note: The job is a remote job and is open to candidates in USA. Whatnot is a live shopping platform where sellers build businesses across many product categories. The AI Tooling Engineer will build internal AI tools, prototypes, automations, and workflows, taking ambiguous cross-organizational opportunities from discovery through production. The role also defines reusable AI patterns, integrates tools with internal systems, and enables teams across the company to adopt AI effectively.

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 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 making the build-vs-buy calls

Skills

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

Benefits

• Offers Equity
• 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
• 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)
• Pension plans internationally
• Monthly allowance to dogfood the app
• 16 weeks of paid parental leave + one month gradual return to work

Company Overview

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