Software Engineer, AI Dev Tools

Whatnot•Los Angeles, CA

11h•Hybrid

About The Position

We’re looking for a Senior Software Engineer to join our Developer Tools team and be a primary contributor of our AI Tooling work end-to-end. In this role, you will build and own the AI tooling that shapes how Whatnot’s engineering organization—and increasingly, non-engineering teams—write code, ship software, and operate systems faster and more effectively. This is not a machine learning or data science role. You won’t be training models—you’ll be building the tooling, infrastructure, and workflows that allow AI coding agents and assistants to operate effectively within Whatnot’s codebase and processes. You should be deeply familiar with the current generation of AI development tools, especially tools provided by the big 3 LLM companies (Anthropic, OpenAI, Google) and have broad knowledge of other AI and LLM products and services. Critically, you must be a strong software engineer first. You’ll serve as the primary interface between the Developer Tools team and Whatnot’s AI Tooling Working Group—a cross-functional community group that tracks the bleeding-edge frontier of AI tooling. You’ll gather feedback, identify high-impact opportunities, and feed that context into the team’s roadmap and build priorities. You will work on all aspects of AI tooling, including: Building and shipping AI tooling across the full spectrum—from near-term developer productivity wins to long-term autonomous agent capabilities—while helping shape what we prioritize next based on what you see working (and not working) on the ground Designing and building sandboxed, containerized environments where AI agents can operate autonomously—running code, executing tests, and iterating on solutions with appropriate guardrails Building multi-agent orchestration systems and workflows, including CI-fixing agents, SRE context agents, and other autonomous AI capabilities that reduce toil and accelerate delivery Enabling non-engineers (PMs, designers, operations) to leverage AI tools effectively through purpose-built workflows, onboarding experiences, and low-code/no-code interfaces Building and optimizing AI-aware developer infrastructure: CLAUDE.md configurations, MCP servers, prompt engineering frameworks, and context management systems that make AI assistants more effective in our codebase Deploying, monitoring, and maintaining the infrastructure supporting AI tools and workflows to ensure high availability, performance, and reliability for the organization. Evaluating and integrating emerging AI tools and platforms as the landscape evolves—staying ahead of the curve and bringing the best of the ecosystem into Whatnot This is a high-visibility, high-autonomy role. You'll have significant ownership over a space that is evolving rapidly, is a top strategic priority for Whatnot's engineering leadership, and directly shapes how our engineers work every day. We offer flexibility to work from home or our office hub, and we value in-person time for planning, problem-solving, and connection. Team members in this role must live within commuting distance of our Los Angeles or San Francisco hubs.

Requirements

5+ years of software engineering experience, with a strong track record of building and shipping production systems.
You're a software engineer first—backend-leaning is fine, but you're comfortable getting around a frontend codebase too, and ideally have enough breadth across different stacks to understand what good tooling looks like beyond your home turf.
A genuine developer tooling enthusiast who's built or improved internal tools, obsessed over local dev ergonomics, or contributed to platform infrastructure—and ideally owned some of it in production.
You see AI not just as autocomplete, but as a catalyst for reimagining how developers interact with their environments, codebases, and workflows.
Deeply familiar with the current generation of AI coding tools—Claude Code (strongly preferred), Cursor, Codex, or similar—and use them to get real work done. You have strong opinions about where this space is heading and don't need to chase every new release to stay effective.
Strong product thinking—you can translate ambiguous problem spaces into concrete plans and prioritize across competing initiatives.
You’re comfortable writing a technical design doc and can clearly communicate what you’re building and why to people outside your team.
Clear communicator who adapts naturally to your audience—whether that’s pairing with a staff engineer on an integration, onboarding a PM onto an AI workflow, or fielding questions from our VP of Engineering or CPO.

Nice To Haves

experience with agent sandboxing, containerized execution environments, multi-agent orchestration, LLM APIs and observability, prompt engineering at scale, or enabling non-technical users to leverage AI-powered workflows.

Responsibilities

Building and shipping AI tooling across the full spectrum—from near-term developer productivity wins to long-term autonomous agent capabilities—while helping shape what we prioritize next based on what you see working (and not working) on the ground
Designing and building sandboxed, containerized environments where AI agents can operate autonomously—running code, executing tests, and iterating on solutions with appropriate guardrails
Building multi-agent orchestration systems and workflows, including CI-fixing agents, SRE context agents, and other autonomous AI capabilities that reduce toil and accelerate delivery
Enabling non-engineers (PMs, designers, operations) to leverage AI tools effectively through purpose-built workflows, onboarding experiences, and low-code/no-code interfaces
Building and optimizing AI-aware developer infrastructure: CLAUDE.md configurations, MCP servers, prompt engineering frameworks, and context management systems that make AI assistants more effective in our codebase
Deploying, monitoring, and maintaining the infrastructure supporting AI tools and workflows to ensure high availability, performance, and reliability for the organization.
Evaluating and integrating emerging AI tools and platforms as the landscape evolves—staying ahead of the curve and bringing the best of the ecosystem into Whatnot

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
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
Parental Leave
16 weeks of paid parental leave + one month gradual return to work company leave allownces run concurrently with country leave requirements which take precedence