About ShiftKey

ShiftKey is a platform that is disrupting the way healthcare facilities find licensed and certified professionals to fill available shifts. Leveraging marketplace dynamics and deep industry knowledge, the company is playing a vital role in mitigating America’s healthcare staffing shortages, enabling direct connections between facilities and healthcare professionals. By offering the opportunity to work as much or as little as they choose and putting the power back into the hands of healthcare workers, ShiftKey is bringing more licensed professionals back into the workforce, a solution that is solving a major crisis in healthcare. For more information, visit www.ShiftKey.com.

The role

ShiftKey is a healthcare workforce marketplace operating in a regulated (HIPAA) environment, and we are building toward being an AI-native company. We are past the experimentation phase but nowhere near done - and that middle stage is exactly why this role exists.

The Staff AI Engineer owns ShiftKey’s AI infrastructure layer: the organizational knowledge platform, the infrastructure for hosting and operating AI agents in the cloud, and the retrieval layer that powers both internal engineering tools and customer-facing capabilities.

A retrieval stack is already in production, serving real workflows today - this is not a from-scratch build. The next layer of the platform is in active development. And the most ambitious parts - richer retrieval over organizational knowledge, agentic infrastructure, the platform API surface, and the cost-governance model that keeps running within budget in a regulated environment - are yours to architect and own.

You will not be maintaining someone else’s finished platform, and you will not be starting from a blank page. You will inherit serious retrieval foundations and own architecture of everything that comes next. You will have high autonomy and organization-wide influence, partnering directly with the platform team, AI ambassadors across engineering, and senior engineering leadership.

Where you’ll work

This is a fully remote position based in the United States. You should be comfortable working asynchronously and partnering with teammates in different time zones.

What you’ll be doing

Evolving the AI knowledge platform - taking the retrieval, indexing, and synthesis layer (currently semantic RAG + re-ranking + HyDE) to an organization-wide platform serving both internal engineering tools and customer-facing capabilities.
Architecting and operating agentic infrastructure on AWS - multi-step, tool-using AI systems that plan, retrieve, and act on complex queries and operational events, with cost guardrails and observability built in from day one.
Designing and building graph-based, relationship-aware retrieval across the organization's data sources, enabling multi-hop queries and letting agents accumulate organizational knowledge over time. This is on our roadmap, not in production - you will define the approach.
Partnering with product engineering to define the AI platform API surface, translating infrastructure primitives into developer-ready abstractions.
Building reference agent implementations on the platform - operational-incident triage, customer support, and future agentic use cases - grounding each agent's reasoning in institutional knowledge.
Owning the AI infrastructure cost model: monitoring compute, model, and storage spend, flagging anomalies, and proposing guardrails to keep workloads within defined budgets.

What you’ll need

7+ years of professional software engineering experience, with at least 2 years building and operating production AI/LLM application systems - not research, not prototyping, not demos.
Retrieval engineering beyond the basics. Our stack already includes re-ranking and HyDE; we need someone who has worked at or above that level: hybrid search, re-ranking, query transformation, context-window management, and evaluation of retrieval quality in production.
Working experience with agentic frameworks and multi-step reasoning loops - tool use, iteration control, cost governance, and model routing trade-offs.
Production-grade software engineering fluency (strict typing, testing, async/concurrency, modern toolchain) in Go, Python, or TypeScript, with the ability to ramp into another quickly.
Hands-on experience operating AI workloads on a managed cloud AI platform (AWS Bedrock or Azure AI Foundry), including the identity/secrets model and model access governance. Bedrock preferred given our AWS stack.
Hands-on Terraform experience - able to author and provision new infrastructure independently, not just modify existing modules.
Familiarity with production observability for AI systems: metrics, structured logging for model spend and latency, and evaluation harnesses to detect regressions.
Understanding of HIPAA-style data-handling requirements in a regulated SaaS environment. Prior healthcare experience is a plus, not a requirement.

Perks of working for ShiftKey

Inclusive and collaborative work environment where all voices are valued.
Hybrid-friendly office spaces designed to be fun and engaging.
Comprehensive health, vision, and dental coverage.
Benefits begin on your first day.
Generous PTO and company-paid holidays, including flexible floating holidays.
100% 401(k) employer match up to 6%.
Paid parental leave.
Wellness support, including access to mental health resources.

#LI-Remote

Our Commitment to Diversity

ShiftKey is an equal opportunity employer and is committed to embracing diverse and individual perspectives shaping our culture and contributing to the solutions that transform the world. We actively work to create an inclusive environment for employees to thrive.

EEO Statement

ShiftKey does not discriminate based on race, religion, color, sex, gender, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status, or any other basis covered by applicable law. All employment is decided based on qualifications, merit, and business needs. ShiftKey is committed to providing reasonable accommodation to applicants with a mental or physical disability, please contact: accommodations@shiftkey.com