
Staff Software Engineer (AI-Native Systems)
Wheel
Job description
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A staff-level engineer who sets technical direction for agentic systems and then leads the work to ship them
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You’ve built and operated agents in production, you know where they break, and you have opinions — held loosely, argued well — about how to build them so they hold up in a regulated environment
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You operate with the scope of a domain owner, not a task owner
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You take a problem that isn’t yet well-formed, define it, sequence it, and lead a group of engineers to a shipped and measured outcome
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Your impact shows up in other people’s work as much as your own: the patterns they reuse, the design decisions they don’t have to relitigate, the ambiguity you removed before it cost the team a quarter
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You treat AI two ways at once — as a product capability you build with judgment, and as a development multiplier you use fluently — and you’re the person who raises the org’s bar on both
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Technical Leadership & Direction
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Own the technical direction for a significant AI-native domain: agent architecture, platform abstractions, or evaluation and guardrail infrastructure
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Act as tech lead for a squad or a cross-team initiative — decomposing ambiguous problems, sequencing delivery, identifying and clearing blockers, and keeping the team pointed at the outcome rather than the ticket
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Write and review design docs; make and document the load-bearing architectural calls, including the ones where the answer is “not yet” or “buy, don’t build.”
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Establish clear technical ownership where it’s currently diffuse, so decisions have a named owner and reviews don’t stall
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Agent Architecture & Engineering
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Design and build production AI agents incorporating retrieval, orchestration, policy-based routing, tool invocation, evaluation harnesses, and lifecycle observability
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Set the standards for what “production-ready agent” means here — testability, rollback safety, cost ceilings, failure modes, human-in-the-loop boundaries — and hold the bar in review
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Take on the hardest parts of the build yourself. This is a hands-on role; you are expected to be in the code
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AI Platform Foundations
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Build and extend the abstraction layers that let teams integrate AI capabilities cleanly and safely across our services
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Define the shared libraries, patterns, and guardrails other teams build on, and drive their adoption — a pattern nobody uses isn’t a pattern
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Treat responsible use of AI on sensitive data as a hard engineering requirement, and translate privacy, security, and compliance constraints into concrete architecture rather than deferring them
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Cloud-Native Engineering
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Own full-stack delivery in TypeScript/Node.js and Python: service and API layers, data-processing jobs, and the internal interfaces on top of them
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Leverage modern cloud infrastructure, event-driven patterns, CI/CD, and observability to deliver scalable AI-native systems
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Own deployment, monitoring, and troubleshooting in production, including on-call, and improve the operational posture of what you inherit
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Stakeholder Engagement & Advisory
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Partner directly with product, operations, clinical operations, and business leaders as both technologist and trusted advisor — helping define which use cases are worth building and which aren’t
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Lead design sessions, proofs of concept, and build-with sessions alongside the people who’ll use the workflows, building trust and adoption as you go
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Communicate trade-offs, risks, and recommendations clearly to technical and non-technical audiences, up to and including the executive team
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Influence roadmap and prioritization with a clear-eyed read of technical risk, sequencing, and cost
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Measure & Improve
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Own the evaluation strategy for your domain: define the metrics, test harnesses, and evaluation plans that measure agent accuracy, latency, safety, and cost-effectiveness
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Instrument the systems so their behavior is legible after the fact, not just at demo time
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Iterate rapidly on data, feedback, and changing requirements — and kill approaches that aren’t working, early and visibly
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Growing the Org
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Mentor and grow engineers through code review, design review, pairing, and direct feedback; make the people around you measurably better
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Craft reusable patterns, documentation, and best practices that raise the engineering bar beyond your own team
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Anchor our internal community of practice around AI-native and agentic engineering
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What success looks like
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First 90 days: you have a working map of our AI platform surface area, have shipped something real, and have a point of view on where the leverage is
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First 6 months: you own a domain outright, are leading a team’s technical direction within it, and there’s an evaluation story for the agents you’ve shipped
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First year: patterns you established are in use by teams you don’t sit on, and engineers point to you as the reason their work got better
Benefits
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Medical, vision, and dental insurance
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Flexible PTO policy
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$500 home office stipend
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Flexible WFH policy
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Paid parental leave
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$5250 personal growth stipend- Fluency with relational data and SQL
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A track record of technical leadership as an individual contributor: owning a domain, leading multi-engineer efforts to completion, and driving decisions across team boundaries without positional authority
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A working practice of using AI development tools as a force multiplier, with judgment about when to trust, verify, or override them
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8+ years building and operating production software, with meaningful full-stack depth across a TypeScript/Node.js backend and at least one other language (Python strongly preferred)
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Strong cloud-native engineering fundamentals; comfort with CI/CD, observability, and running what you build
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Demonstrated ability to take a loosely defined problem and drive it to a shipped, measured, agent-powered workflow
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Comfort with ambiguity and a bias toward shipping measurable results
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Hands-on experience designing and deploying agentic systems in production — retrieval, orchestration, tool/function calling, and evaluation — with a clear-eyed view of where LLMs and agents work and where they don’t
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Clear written and verbal communication, including the ability to write a design doc that changes minds. This is a remote, cross-functional role
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Experience with agent frameworks and multi-agent architectures at production scale
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Model evaluation and guardrail infrastructure — measuring output quality, catching regressions, keeping agents inside safe bounds
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Experience building platform capabilities consumed by other engineering teams
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Background in workflow automation, forecasting-driven products, or supply-demand matching
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Prior work in a regulated environment (healthcare/HIPAA, fintech, etc.) and an instinct for the constraints that come with using AI on sensitive data
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Experience mentoring engineers or acting as a formal tech lead