Staff Software Engineer - AI Platform Engineer

The Staff Software Engineer (AI Platform Engineer) is responsible for driving AI-first engineering across WellSky by architecting and building agentic solutions, automating developer workflows, and enabling engineers and the Solutions organization to deliver faster and better. The scope of this job includes setting the technical direction for agentic AI development on the Engineering Enablement team, leading org-wide enablement and training, and partnering with product engineering teams and the Solutions organization to integrate agentic workflows into the software development lifecycle and customer delivery processes. Key Responsibilities: Architect and build agentic AI solutions — including autonomous workflows, tool-calling agents, RAG pipelines, and LLM integrations — that are used daily by WellSky engineers and the Solutions organization. Set the technical direction for AI-first engineering on the Engineering Enablement team, guiding the Senior Software Engineer and defining standards for agentic development, prompt engineering, context management, and LLM integration across WellSky repositories. Own the AI enablement platform: agent skills, CI/CD automation, developer tooling, and shared libraries that raise the productivity floor for the entire engineering organization. Lead training sessions, workshops, demos, and office hours that build AI-first engineering skills and practices across WellSky’s engineering organization. Partner with the Solutions organization to identify opportunities and integrate agentic workflows into SDLC and customer-facing delivery processes. Embed directly with product engineering teams to identify where agentic AI delivers real value, then build and hand off the tooling that makes adoption stick. Evaluate agent output quality, establish evaluation and observability practices, and ensure AI tooling is safe and reliable before rollout. Serve as WellSky’s internal authority on agentic AI development patterns, emerging tooling, and best practices. Write clear, high-quality documentation, guides, and enablement materials consumed by hundreds of engineers. Collaborate with engineering leaders to prioritize the highest-value AI enablement opportunities across the organization. Perform other job duties as assigned. Required Qualifications: Bachelor’s degree in a related field, or equivalent work experience. 8-12 years of relevant software engineering experience, with substantial depth in .NET / C#. At least 2 years of hands-on experience developing with LLMs, including a minimum of 1 year architecting and building agentic AI solutions — agentic workflows, tool/function calling, RAG, prompt and context engineering, and agent evaluation. Must have shipped agentic systems to production that are used by real users; prototypes and proofs of concept alone do not meet this bar. Strong, current .NET / C# skills (.NET 8 or newer, ASP.NET Core); must be able to work directly in WellSky’s .NET codebases and embed with .NET product teams. Proficiency in Python, the primary language for AI tooling, agent platforms, and data pipelines on this team. Experience building internal developer tools, CI/CD automation, or shared libraries for other engineers — not just product features. Hands-on experience integrating LLM APIs (Anthropic, OpenAI, or Vertex AI), including tool/function calling and streaming at production scale. Daily use of AI-assisted development tools such as Claude Code, GitHub Copilot, or Cursor. Demonstrated ability to lead technical direction, guide senior engineers, and drive adoption of new practices across a team or organization. Excellent written communication skills; comfortable producing documentation and enablement materials for a large technical audience. Comfortable running training, demos, and office hours for engineers at all levels. Preferred Qualifications: TypeScript / JavaScript proficiency; React experience strongly preferred. Experience with event-driven messaging systems — Apache Kafka, Google Pub/Sub, Azure Service Bus, or RabbitMQ (Kafka is the standard on our go-forward platform). Experience with Model Context Protocol (MCP) — building MCP servers, clients, and agent integrations (strong differentiator). PostgreSQL and vector database experience — pgvector, Pinecone, Weaviate, or Vertex AI Search. Google Cloud Platform experience — Cloud Run, Vertex AI, GKE (Azure or AWS also considered). LLM evaluation and observability experience — evals, tracing, prompt regression testing. Familiarity with agent and LLM frameworks such as Claude Agent SDK, Semantic Kernel, Microsoft.Extensions.AI, LangChain, or LangGraph. Domain-Driven Design and CQRS experience (MediatR or equivalent). OpenTelemetry and distributed tracing experience — Jaeger, Seq, Datadog, or Grafana. Experience guiding or mentoring senior engineers. Healthcare industry experience preferred; HIPAA and PHI handling experience weighted highly. Consulting instinct — able to embed with a team, diagnose where AI actually helps, and say no clearly where it does not. High tolerance for ambiguity and a fast-moving tooling landscape. Job Expectations: Willing to work additional or irregular hours as needed Must work in accordance with applicable security policies and procedures to safeguard company and client information Must be able to sit and view a computer screen for extended periods of time #LI-TC1 #LI-Remote WellSky is where independent thinking and collaboration come together to create an authentic culture. We thrive on innovation, inclusiveness, and cohesive perspectives. At WellSky you can make a difference. Here are some of the exciting benefits full-time teammates are eligible to receive at WellSky: Excellent medical with Rx, dental, and vision benefits Mental Health support through EAP Generous paid time off, plus 13 paid holidays 100% vested 401(K) retirement plans Educational assistance up to $2500 per year WellSky provides equal employment opportunities to all people without regard to race, color, national origin, ancestry, citizenship, age, religion, gender, sex, sexual orientation, gender identity, gender expression, marital status, pregnancy, physical or mental disability, protected medical condition, genetic information, military service, veteran status, or any other status or characteristic protected by law. WellSky is proud to be a drug-free workplace. Applicants for U.S.-based positions with WellSky must be legally authorized to work in the United States. Verification of employment eligibility will be required at the time of hire. 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