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Staff Software Engineer (AI-Native Systems)

Wheel

Remotelead$186k–$265kPosted 11h ago

Job description

  • A staff-level engineer who sets technical direction for agentic systems and then leads the work to ship them

  • 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

  • You operate with the scope of a domain owner, not a task owner

  • 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

  • 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

  • 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

  • Technical Leadership & Direction

  • Own the technical direction for a significant AI-native domain: agent architecture, platform abstractions, or evaluation and guardrail infrastructure

  • 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

  • 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.”

  • Establish clear technical ownership where it’s currently diffuse, so decisions have a named owner and reviews don’t stall

  • Agent Architecture & Engineering

  • Design and build production AI agents incorporating retrieval, orchestration, policy-based routing, tool invocation, evaluation harnesses, and lifecycle observability

  • 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

  • Take on the hardest parts of the build yourself. This is a hands-on role; you are expected to be in the code

  • AI Platform Foundations

  • Build and extend the abstraction layers that let teams integrate AI capabilities cleanly and safely across our services

  • Define the shared libraries, patterns, and guardrails other teams build on, and drive their adoption — a pattern nobody uses isn’t a pattern

  • 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

  • Cloud-Native Engineering

  • 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

  • Leverage modern cloud infrastructure, event-driven patterns, CI/CD, and observability to deliver scalable AI-native systems

  • Own deployment, monitoring, and troubleshooting in production, including on-call, and improve the operational posture of what you inherit

  • Stakeholder Engagement & Advisory

  • 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

  • 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

  • Communicate trade-offs, risks, and recommendations clearly to technical and non-technical audiences, up to and including the executive team

  • Influence roadmap and prioritization with a clear-eyed read of technical risk, sequencing, and cost

  • Measure & Improve

  • Own the evaluation strategy for your domain: define the metrics, test harnesses, and evaluation plans that measure agent accuracy, latency, safety, and cost-effectiveness

  • Instrument the systems so their behavior is legible after the fact, not just at demo time

  • Iterate rapidly on data, feedback, and changing requirements — and kill approaches that aren’t working, early and visibly

  • Growing the Org

  • Mentor and grow engineers through code review, design review, pairing, and direct feedback; make the people around you measurably better

  • Craft reusable patterns, documentation, and best practices that raise the engineering bar beyond your own team

  • Anchor our internal community of practice around AI-native and agentic engineering

  • What success looks like

  • 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

  • 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

  • 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

  • Medical, vision, and dental insurance

  • Flexible PTO policy

  • $500 home office stipend

  • Flexible WFH policy

  • Paid parental leave

  • $5250 personal growth stipend- Fluency with relational data and SQL

  • 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

  • A working practice of using AI development tools as a force multiplier, with judgment about when to trust, verify, or override them

  • 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)

  • Strong cloud-native engineering fundamentals; comfort with CI/CD, observability, and running what you build

  • Demonstrated ability to take a loosely defined problem and drive it to a shipped, measured, agent-powered workflow

  • Comfort with ambiguity and a bias toward shipping measurable results

  • 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

  • Clear written and verbal communication, including the ability to write a design doc that changes minds. This is a remote, cross-functional role

  • Experience with agent frameworks and multi-agent architectures at production scale

  • Model evaluation and guardrail infrastructure — measuring output quality, catching regressions, keeping agents inside safe bounds

  • Experience building platform capabilities consumed by other engineering teams

  • Background in workflow automation, forecasting-driven products, or supply-demand matching

  • Prior work in a regulated environment (healthcare/HIPAA, fintech, etc.) and an instinct for the constraints that come with using AI on sensitive data

  • Experience mentoring engineers or acting as a formal tech lead