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Principal Software Engineer
About the Company
Our client is a unicorn-valued healthcare technology company building the operating system for independent medical practices across the United States. Their integrated platform serves over 140,000 providers and unifies clinical documentation, billing, scheduling, patient engagement, and practice marketing into a single purpose-built solution. With significant fresh financing closed and a clear mandate to accelerate AI across every layer of the product, the company is in the midst of a meaningful technology transformation — and this role sits at the centre of it.
About the Role
You'll operate at the intersection of hands-on engineering and senior technical leadership — owning architectural direction, writing production code, and tackling the kinds of complex problems that require both depth and creativity. Equally important is your ability to lead: mentoring engineers, aligning teams, and setting the technical bar across a strong, full-stack engineering organization. A central part of this role is driving the company's push into AI — embedding intelligent capabilities into the product and modernizing how the engineering team itself works. If you're someone who already lives and breathes AI in your day-to-day and wants to bring that energy to a team that's genuinely committed to the transformation, this is worth a conversation.
What You'll Be Doing
- AI Integration: Contribute to the integration of AI capabilities within the core product — working with LLMs, RAG pipelines, and agentic workflows — while championing AI tooling adoption across the SDLC.
- Architecture & Execution: Lead system design and contribute hands-on code for large-scale, complex backend systems with full-stack fluency where needed.
- Domain Mastery: Build genuine depth across the product, the technical stack, and the broader AI ecosystem.
- Problem Ownership: Bring creative, pragmatic thinking to hard technical challenges with a clear focus on customer outcomes.
- Collaboration: Work closely with product, QA, and DevOps partners to drive alignment and move initiatives forward effectively.
- Technical Governance: Shape and review architectural decisions to ensure consistency, scalability, and future-readiness.
- Team Development: Give engineers clear, actionable technical feedback and actively raise the team's capability in modern AI engineering practices.
What You Bring
- Experience: 12+ years in software engineering with confirmed Principal-level tenure — seasoned enough to add immediate value to a strong, experienced team.
- AI Mindset: AI is already embedded in your daily workflow — you use it to write code, investigate problems, generate tests, and accelerate delivery. You're a genuine advocate, not a sceptic.
- Languages: Strong in Python, Java, or TypeScript; comfortable navigating across all three over time.
- Frameworks: Experience across some combination of Vue, React, Flask, and Spring Boot. Full-stack fluency valued — deep backend with working frontend knowledge is the target profile.
- Cloud: AWS primary; GCP familiarity a plus.
- Databases: Comfortable across relational and NoSQL — MySQL, PostgreSQL, DynamoDB, Firestore. Vector database experience a plus.
- AI Delivery: Hands-on experience with LLMs, RAG, or agentic AI in production is a strong differentiator. LangChain, LlamaIndex, or similar orchestration frameworks a bonus.
- Product Shop Background: You've built and owned software in a product company — not an agency, consultancy, or pure freelance context. You understand what it means to be a true team member across engineering, product, and QA.
- Influence: The kind of engineer others seek out — trusted for technical judgement, clear in how you communicate it.
- Communication: Can translate complex technical concepts clearly for both engineering and non-technical audiences.
Compensation:
- $180,000-$230,000 CAD
- Unlimited Vacation
- Excellent benefits inc. Medical/Dental/Vision
The base pay range for this role is CA$180,000 – CA$230,000 per year.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
