Software Engineer, AI Dev Tools

Whatnot is the largest livestream shopping platform in North America and Europe to buy, sell, and discover the things you love. Whether it's trading cards, fashion, electronics, or live plants, our sellers are building real businesses across hundreds of categories. We're building live commerce at a scale that's never been done in the West, and there's no playbook to copy. The people here are shaping how an entirely new industry develops.

As a remote co-located team, we're inspired by our values and anchored in hubs across the US, UK, Ireland, Poland, Germany, and Australia. We move fast, stay close to our users, and focus on the work that drives the most impact.

We're one of the fastest growing marketplaces and were recently named the #1 Best Startup Employer in America by Forbes. Check out the latest Whatnot updates on our news and engineering blogs and join us as we enable anyone to turn their passion into a business and bring people together through commerce.

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.

• 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.

Curious about who thrives at Whatnot? We’ve found that embodying a low ego, growth mindset, and high-impact drive goes a long way here.

• 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. The people you work with will span the full spectrum of technical ability.

• Bonus: 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.

• 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

  • 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 allownces run concurrently with country leave requirements which take precedence

Whatnot is 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.