[![Image]() Meet Jobicy Copilot — free AI autofill for job applications + remote job alerts ›](#)   [All remote jobs](https://jobicy.com/jobs.md)Open role[![Wheel logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/01/WRILS-210112005722-210970.jpg)](https://jobicy.com/company/wheel.md)Remote opportunity at[Wheel](https://jobicy.com/company/wheel.md)

# Staff Software Engineer, AI-Native Systems

Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move.

[Apply for this job](#job-application)[View company](https://jobicy.com/company/wheel.md)Share15 Sep 2026Published31Listing views1Application actions15 Oct 2026Apply before  Opportunity details

## About this role.

AI SummaryWheel is hiring a Staff Software Engineer and technical lead to set direction and deliver production AI-native systems for a regulated virtual-care platform. The role combines hands-on full-stack engineering in TypeScript/Node.js and Python with technical leadership across agent architecture, evaluation, guardrails, cloud operations, and platform foundations. The engineer will lead ambiguous cross-functional initiatives, establish reusable engineering patterns, and mentor other engineers. Success depends on safely deploying observable, measurable AI agents that handle sensitive healthcare data while balancing accuracy, latency, cost, and operational risk.

## Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

### Job Complexity

5/5EasyHard

### Pace & Pressure

5/5RelaxedFast-paced

### Autonomy Level

5/5GuidedFull ownership

### Communication Load

5/5IndependentCollaborative

AI insightThis is a staff-level, hands-on technical leadership role requiring production agentic-AI expertise, full-stack depth, cloud operations ownership, and architectural judgment in a regulated healthcare setting. The role also demands independent domain ownership and influence across engineering, product, operations, clinical teams, and executives.

## Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job medianHighly competitive$225,113US market range$186k–$265k0$291k

AI insightThe disclosed US yearly pay range is $185,725 to $264,500 USD, with a midpoint of $225,112.50. This range is consistent with a senior staff-level software engineering and AI technical-lead role in the US; the disclosed range is used as the market range for this analysis.

## Core skills

Skills and capabilities most closely associated with this opportunity.

[Staff software engineering](https://jobicy.com/jobs?search_keywords=Staff%20software%20engineering.md)[Technical leadership](https://jobicy.com/jobs?search_keywords=Technical%20leadership.md)[Agentic AI](https://jobicy.com/jobs?search_keywords=Agentic%20AI.md)[LLM orchestration](https://jobicy.com/jobs?search_keywords=LLM%20orchestration.md)[TypeScript](https://jobicy.com/jobs?search_keywords=TypeScript.md)[Node.js](https://jobicy.com/jobs?search_keywords=Node.js.md)[Python](https://jobicy.com/jobs?search_keywords=Python.md)[Cloud-native systems](https://jobicy.com/jobs?search_keywords=Cloud-native%20systems.md)[AI evaluation and guardrails](https://jobicy.com/jobs?search_keywords=AI%20evaluation%20and%20guardrails.md)[Healthcare compliance](https://jobicy.com/jobs?search_keywords=Healthcare%20compliance.md)

Sample interview questionsDescribe a production AI agent you designed and operated. How did you handle retrieval, tool use, failures, and observability?I would explain the workflow boundary first, then describe the retrieval strategy, orchestration logic, tool contracts, and policy checks. I would include failure handling such as timeouts, retries, fallbacks, human escalation, and rollback paths, along with dashboards and traces measuring quality, latency, cost, tool failures, and user outcomes.

How would you define a production-readiness standard for an AI agent handling sensitive healthcare data?

I would require clear allowed-use boundaries, data minimization, access controls, audit logging, evaluation datasets, regression gates, prompt and model versioning, cost limits, and explicit human-in-the-loop escalation criteria. The system should have measurable safety and quality thresholds, rollback capability, and operational ownership before broad release.

Tell us about a time you turned an ambiguous problem into a delivered cross-team technical outcome without formal authority.

A strong answer would outline how I framed the problem, gathered stakeholder input, documented decision options and trade-offs, divided the work into sequenced milestones, and created clear ownership. I would quantify the shipped outcome and describe how I resolved blockers and aligned teams through technical evidence rather than hierarchy.

How would you design an evaluation strategy for an agentic workflow?

I would start with the workflow's intended business and safety outcomes, then build representative test sets covering normal, edge, and adversarial cases. I would measure task success, factuality, policy adherence, escalation quality, latency, reliability, and unit cost, using offline regression tests plus production monitoring and sampled human review.

How do you balance rapid AI experimentation with engineering reliability and regulatory constraints?

I separate low-risk experimentation from production pathways and use staged releases, feature flags, evaluation gates, and tightly scoped data access. I communicate the risk and expected value of each experiment, instrument it from the beginning, and stop or redesign approaches quickly when evidence shows they do not meet safety, quality, or cost requirements.

### Staff Software Engineer, AI-Native Systems (Tech Lead)

Location: Remote (US)

### We are

Virtual care only works if the infrastructure behind it does. Wheel builds that infrastructure — the systems that let telehealth run at scale for the patients, clinicians, and companies depending on it. We’re not bolting AI onto old workflows; we’re rebuilding them from the ground up. Our mission to put great healthcare in everyone’s reach means replacing manual, ad-hoc processes with intelligent, agent-powered systems that carry real operational load. We’re innovating in a live, regulated healthcare environment where getting it right matters. This is the next architecture of virtual care, and we’re building it now.

### You are

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.

### The Work

### 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.

### What we’re looking for

*

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).

*

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.

*

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.

*

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

*

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

*

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

*

Fluency with relational data and SQL.

*

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

*

Comfort with ambiguity and a bias toward shipping measurable results.

### Strongly desired

*

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.

### How we work

Remote-first (US), fast-moving, tight loops between engineering, product, and the business. We’re an AI-forward engineering org — we expect AI in the toolchain and in the product, and we measure outcomes over activity. We handle sensitive healthcare data under strict controls; privacy, security, and responsible use of AI are engineering requirements here, not afterthoughts.

### Salary and Perks

Pay Range: $185,725-$264,500 USD

Final offer amounts are determined by multiple factors including, but not limited to, the scope and responsibilities of the role, the selected candidate’s work experience, education and training, the work location as well as market and business considerations.

As an employee of Wheel, you’ll enjoy our Total Rewards Program to help secure your financial future and preserve your health and well-being, including:

*

Medical, Dental and Vision

*

Ancillary: Life, Short and Long Term Disability

*

401K match

*

Flexible PTO

*

Parental Leave

*

Stock options

*

Additional programs and perks

Wheel is committed to equal employment opportunities for all team members. Every decision we make regarding employment is solely based on merit, competence, and performance. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills.

Research shows that underrepresented groups typically apply only if they meet 100% of the criteria listed. At Wheel, we encourage women, people of color, and LGBTQ+ job seekers to apply for positions even if they don’t check every box for the role.

Show more

[Apply now >](https://jobicy.com/jobs/153338-staff-software-engineer-ai-native-systems.md)

*

![Upload CV](data:image/svg+xml;base64,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)

### Upload your resume now

To unlock remote work opportunities and be discovered by global employers.

This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.

Next step

## Apply now.

Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information.

Keep exploring

## Related remote jobs.

Matched by job category10 related opportunities[Software Engineering](https://jobicy.com/categories/engineering.md) [Browse all jobs](https://jobicy.com/jobs.md)
*
![Supabase logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/06/611d3bfa-221.png)
Supabase  Sep 15

### [Postgres Engineer](https://jobicy.com/jobs/153321-postgres-engineer.md)

Supabase is the Postgres development platform, built by developers for developers. We provide a complete backend solution including Database, Auth, Storage, Edge Functions, Realtime, and Vector Search. All services are…

*
![Toptal logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/346ce7fb-221.png)
Toptal  Sep 15

### [Chief Technology Officer](https://jobicy.com/jobs/153308-chief-technology-officer-3.md)

About Toptal Toptal is a global network of top talent in business, design, and technology that enables companies to scale their teams, on-demand. With $200+ million in annual revenue and…

*
![Zuora logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/43baa0bd-221.jpg)
Zuora  Sep 15

### [Customer Solutions Engineer – Payments](https://jobicy.com/jobs/149199-customer-solutions-engineer-payments.md)

About ZuoraAt Zuora, we help businesses grow smarter and adapt faster. Our platform powers modern business models — from subscriptions and usage-based pricing to AI-driven and outcome-based offerings — helping…

*
![Fleetio logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2023/07/e571b83c37e0ed5371754d319be16e76.jpeg)
Fleetio  Sep 15

### [Director of Engineering, Leverage](https://jobicy.com/jobs/150772-director-of-engineering-leverage.md)

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge…

*
![Meta logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/750f86a9-221.jpeg)
Meta  Sep 15

### [Software Engineer (Technical Leadership)](https://jobicy.com/jobs/150665-software-engineer-technical-leadership.md)

Meta is seeking a Software Engineer to join our engineering team. The ideal candidate will have industry experience working on a range of classification and optimization problems like payment fraud,…

*
![Ashby logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/63864ee6-221.png)
Ashby  Sep 15

### [Engineering Manager – EU](https://jobicy.com/jobs/150687-engineering-manager-eu.md)

Hi 👋 I’m Colin, Director of Engineering, Europe. How do you feel about software engineers writing product specs, making product decisions, and not breaking down projects into individual tickets? If…

*
![PointClickCare logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/02/94d5c7bae5858d7e126022ed422c639c.jpeg)
PointClickCare  Sep 15

### [Canada- Sr Application Engineer (Salesforce-Agentforce Ai)](https://jobicy.com/jobs/149241-canada-sr-application-engineer-salesforce-agentforce-ai.md)

At PointClickCare our mission is simple: to help providers deliver exceptional care. And that starts with our people. As a leading health tech company that’s founder-led and privately held, we…

*
![AssetWatch logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/118c6be8-221.png)
AssetWatch  Sep 15

### [Head of AI](https://jobicy.com/jobs/149262-head-of-ai.md)

AssetWatch serves global manufacturers by powering manufacturing uptime through the delivery of an unparalleled condition monitoring experience, with a passion to care about the assets our customers care for every…

*
![Cresta logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2022/08/4d686e40b22cf2510b627c59afe5fd95.jpg)
Cresta  Sep 14

### [Senior Frontend Software Engineer (AI Receptionist)](https://jobicy.com/jobs/153297-senior-frontend-software-engineer-ai-receptionist.md)

Cresta unlocks the true potential of the customer experience, turning every conversation into a competitive advantage. Cresta’s unified AI platform combines conversational AI agents, real-time human agent augmentation, and comprehensive…

*
![UpGuard logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/474a12c7-221.png)
UpGuard  Sep 14

### [Manager, GTM Engineering](https://jobicy.com/jobs/153275-manager-gtm-engineering.md)

Who are we? At UpGuard, we are replacing manual security bottlenecks with AI-driven precision. Fresh off a US$75M Series C, we are scaling our infrastructure to process 100 billion risk…