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WellSky Jobs Information

Do workers at WellSky get paid breaks?

Yes. Most people get paid breaks.
67% of people say they get paid breaks.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Does WellSky pay people when they’re sick?

Yes. Most people get paid when they’re sick.
70% of people say they would get paid if they were sick but scheduled to work.
Based on data from 10 people who took the Breakroom Quiz between January 2025 and April 2026.

At WellSky, are sick days and vacation days separate paid time off?

Only some people have separate paid time off for sick days and vacation.
43% of people say they have to use vacation days when they’re out sick.
Based on data from 7 people who took the Breakroom Quiz between June 2025 and April 2026.

Is the health insurance from WellSky affordable enough for their workers?

Most people say the health insurance costs are okay.
100% of people say the health insurance costs are okay
Based on data from 8 people who took the Breakroom Quiz between March 2025 and April 2026.

Do people get paid time off at WellSky?

Most people get paid time off work.
100% of people say they get paid time off.
Based on data from 7 people who took the Breakroom Quiz between June 2025 and April 2026.

Do workers at WellSky worry about hours?

Most people don’t worry about getting enough hours.
80% of people report they don’t worry about getting enough hours.
Based on data from 5 people who took the Breakroom Quiz between January 2025 and August 2025.

How easy is it to get time off at WellSky?

Most people find it easy to get time off.
90% of people report it’s easy to get time off.
Based on data from 10 people who took the Breakroom Quiz between January 2025 and April 2026.

How easy is it to take sick days at WellSky?

Most people find it easy to take sick days.
100% of people report that it’s easy to take time off if they are sick.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at WellSky feel treated with respect by their managers?

Most people feel treated with respect by their managers.
75% of people say they’re treated with respect by their managers.
Based on data from 8 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at WellSky get to take their breaks without interruption?

Only some people get breaks without interruption.
44% of people report that their breaks get interrupted.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Is it stressful to work at WellSky?

Most people feel stressed here.
78% of people say they often feel stressed at work.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at WellSky enjoy their jobs?

Only some people enjoy their job.
44% of people report they don’t enjoy their job.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people at WellSky recommend working with their team?

Only some people recommend working with their team.
40% of people report that they wouldn’t recommend working with their immediate team to a friend.
Based on data from 10 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people get enough training when they start at WellSky?

Most people got enough training when they started.
88% of people report they got enough training when they started working here.
Based on data from 8 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people get support to advance at WellSky?

Only some people are given support to advance their career here.
In the last year, 56% of people report not being given support to advance their career here.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Do people think WellSky’s headquarters understands what’s happening where they work?

Most people think headquarters doesn’t understand what’s happening where they work.
78% of people think that this employer’s headquarters or owners don’t have a good understanding of what’s really happening where they work.
Based on data from 9 people who took the Breakroom Quiz between January 2025 and April 2026.

Do workers feel well informed about how WellSky is doing?

Most people feel well informed about how the company is doing.
88% of people feel that they are kept well informed about how the company is doing as a whole.
Based on data from 8 people who took the Breakroom Quiz between January 2025 and April 2026.

What are the most popular job types at Wellsky?

    What are the most popular categories at Wellsky?

    Infographic showing various Customer Service job openings at Wellsky in the United States as of August 2026, with employment types broken down into 100% Full Time. Highlights an 56% Physical, and 44% Remote job distribution.

    Staff Software Engineer - AI Platform Engineer

    Wellsky

    Overland Park, KS • On-site

    $140 - $200/hr

    Other

    Medical, Dental, Vision, Retirement, PTO

    Posted 23 days ago


    WellSky rating

    7.3

    Company rating: 7.3 out of 10

    Based on 10 frontline employees who took The Breakroom Quiz

    181st of 247 rated software companies


    Job description

    ## Staff Software Engineer - AI Platform EngineerApplyremote type: Onsitelocations: Overland Park, KStime type: Full timeposted on: Posted Yesterdayjob requisition id: JR4931The **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 yearWellSky 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. Certain client-facing positions may be required to comply with applicable requirements, such as immunizations and occupational health mandates. #J-18808-Ljbffr

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