Principal Software Engineer (AI) (CAD) at PointClickCare

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 empower our employees to push boundaries, innovate, and shape the future of healthcare. With the largest long-term and post-acute care dataset and a Marketplace of 400+ integrated partners, our platform serves over 30,000 provider organizations, making a real difference in millions of lives. We also reinvest a significant percentage of our revenue back into research and development, ensuring our employees have the resources to innovate and make a lasting impact. Recognized by Forbes as a top private cloud company and honored as one of Canada’s Most Admired Corporate Cultures, we offer flexibility, growth opportunities, and meaningful work.  At PointClickCare, we empower our people to be the architects of a smarter healthcare future; one that is human-first and accelerated by AI to create meaningful and lasting change. Employees harness AI as a catalyst for creativity, productivity, and thoughtful decision-making. By integrating AI tools into our daily workflows, collaboration is enhanced, outcomes are improved, and every team member has the proficiency to maximize their impact. It all starts with our hiring practices where we uncover AI expertise that complements our mission, and we continue to invest in training and development to nurture innovation throughout the employee journey. Join us in redefining healthcare — so it doesn’t just survive, it thrives. To learn more about PointClickCare, check out Life at PointClickCare and connect with us on Glassdoor and LinkedIn. **Travel to Office expectations** For Remote Roles: If this role is remote, there will be in-office events that will require travel to and from the Mississauga and/or Salt Lake City office. These will include, but not limited to, onboarding, team events, semi-annual and annual team meetings. For Hybrid Roles: If this role is Hybrid, there will be an expectation to reside within commutable distance to the office/location specified in the job listing. This will include, but not limited to, weekly/bi-weekly/monthly events in the office with your specific team. This is a requirement for this role.   Team Summary: The role sits within the AI Engineering & Enablement team, which accelerates AI adoption across the PEO by building shared platforms, establishing best practices, and enabling teams to embed AI and data capabilities into their products and workflows.   Job Summary: The Principal AI Engineer is a senior technical leader responsible for driving PointClickCare’s AI first and data first transformation across products and platforms. This role defines and delivers production grade AI systems, including agentic and data driven solutions—that are secure, observable, scalable, and aligned with healthcare regulatory requirements.  Beyond hands on technical leadership, the Principal AI Engineer acts as a coach and mentor to engineering teams, elevating AI and data engineering maturity across the organization. This role partners closely with Product, Engineering, Architecture, Advanced Technology, and SaaS Operations to identify high value opportunities for AI driven innovation and to transition prototypes into reliable, measurable business outcomes.    Key responsibilities: Lead the reference architecture for AI and agentic systems within key product domains, defining standards and reusable patterns for reasoning loops and orchestration, tool/function calling, memory and state management, data integration and retrieval, safety, governance and interoperability. Design and deliver production ready AI systems, ensuring reliability, scalability, observability, performance, and cost efficiency across the full lifecycle.  Establish platform level AI and data components, including Model broker and multi-model routing strategies, orchestration and workflow services, evaluation and experimentation frameworks, prompt, configuration, and versioning systems and telemetry, monitoring, and cost governance tooling. Lead the design of end-to-end AI data pipelines, including document ingestion, OCR, NER, and preprocessing, chunking, embeddings, vector stores, and hybrid search and offline and online evaluation for quality, latency, safety, and cost. Responsibilities Continued: Partner with data and analytics teams to align AI solutions with measurable product and business outcomes.  Partner with Product Management to identify, shape, and validate AI driven opportunities that improve clinical, operational, and business outcomes.  Help product teams move from problem framing to AI enabled solutions, balancing feasibility, value, risk, and regulatory constraints.  Contribute to innovation efforts by evaluating emerging AI tools, models, and frameworks  Prototyping new approaches in collaboration with Advanced Technology  Translating successful experiments into scalable platform capabilities  Ensure all AI solutions are production grade, with strong practices for observability, logging, alerting, and incident response, performance testing and cost optimization, safe rollout, experimentation, and rollback strategies  Embed responsible AI and security by design principles, including RBAC, audit logging, and privacy controls, alignment with healthcare regulations and standards (e.g., HIPAA, NIST AI RMF, ONC aligned guidance) and close collaboration with Security, Privacy, Regulatory, and Platform teams  Mentor and coach senior and intermediate engineers, raising overall capability in AI and data architecture, production AI engineering practices, evaluation, experimentation, and systems thinking  Drive adoption of shared AI and data best practices, enabling teams to reuse platform components, contribute improvements back to shared frameworks, consistently evolve domain specific AI capabilities    Qualification and Skills: Proven experience leading and delivering production AI systems across multiple engineering teams.  Strong background in AI engineering with a data first mindset, including experience with largescale data pipelines and analytics driven evaluation.  Strong background in AI engineering with a data first mindset, including experience with largescale data pipelines and analytics driven evaluation.  Hands on experience extending or building with modern AI/agent frameworks such as LangChain, LangGraph, AutoGen, CrewAI, LlamaIndex, or equivalent.  Deep understanding of RAG and agentic architectures, including embeddings, vector databases, evaluation harnesses, and cost/latency tradeoffs.  Experience designing or contributing to offline and online evaluation methodologies tied to product metrics and business outcomes Experience implementing security by design and responsible AI practices in regulated or enterprise SaaS environments Preferred skills: Experience deploying AI systems in healthcare or other regulated industries (e.g., HIPAA aligned environments).  Familiarity with model serving infrastructure, model broker patterns, and multi-model routing for performance and cost optimization.  Experience partnering closely with Product Management to identify and deliver AI enabled product capabilities.  Master’s degree in Artificial Intelligence, Computer Science, or a related field, or equivalent practical experience.  #LI-AV1 #LI-Remote  PointClickCare Benefits & Perks: Benefits starting from Day 1! Retirement Plan Matching Flexible Paid Time Off Wellness Support Programs and Resources Parental & Caregiver Leaves Fertility & Adoption Support Continuous Development Support Program Employee Assistance Program Allyship and Inclusion Communities Employee Recognition … and more! It is the policy of PointClickCare to ensure equal employment opportunity without discrimination or harassment on the basis of race, religion, national origin, status, age, sex, sexual orientation, gender identity or expression, marital or domestic/civil partnership status, disability, veteran status, genetic information, or any other basis protected by law. PointClickCare welcomes and encourages applications from people with disabilities. Accommodations are available upon request for candidates taking part in all aspects of the selection process. Please contact [Upgrade to PRO to see contact] should you require any accommodations. As part of our commitment to a streamlined and equitable hiring experience, PointClickCare uses AI tools to assist with candidate screening and assessment. When you apply for a position, your information is processed and stored with Lever, in accordance with Lever’s Privacy Policy. We use this information to evaluate your candidacy for the posted position. We also store this information, and may use it in relation to future positions to which you apply, or which we believe may be relevant to you given your background. When we have no ongoing legitimate business need to process your information, we will either delete or anonymize it.  If you have any questions about how PointClickCare uses or processes your information, or if you would like to ask to access, correct, or delete your information, please contact PointClickCare’s human resources team: [Upgrade to PRO to see contact]  PointClickCare is committed to Information Security. By applying to this position, if hired, you commit to following our information security policies and procedures and making every effort to secure confidential and/or sensitive information.