Staff Software Engineer, AI Engineering

About the Company A well-funded health tech unicorn ($250M financing closed late 2024) building the full operating system for independent medical practices across the US. The platform serves over 140,000 providers and covers the complete practice lifecycle — clinical infrastructure, billing, compliance, revenue cycle management, and patient acquisition. A significant portion of recent funding is mandated for a root-to-branch AI transformation across the entire product and business.

The engineering culture is senior, stable, and high-retention — average tenure on the team is six to seven years.

The Role The Revenue Cycle Management team is seeking a Staff Software Engineer to lead the design, development, and adoption of AI-native capabilities across their billing and revenue cycle platform.

This role sits at the intersection of Java backend engineering and applied AI systems. You will own both the platform engineering layer and the AI transformation on top of it — designing and shipping production-grade agentic workflows, RAG systems, and intelligent automation that replace manual complexity in US medical billing. The mandate is greenfield: a brand new AI-native billing platform built from scratch, with a real end-of-year launch target.

What You'll Work On

- Design and build production-ready AI-enabled services that combine Java backend logic, APIs, and LLM-powered capabilities to support real billing and revenue cycle workflows
- Architect and implement agentic AI workflows — multi-step orchestration, stateful execution, tool use,



and human-in-the-loop patterns — on top of a high-throughput Java/Spring Boot platform
- Build and operate RAG pipelines including embeddings, vector search, retrieval architecture, and hallucination mitigation for enterprise clinical and billing data
- Integrate LLMs and external AI services into existing systems using strong engineering patterns for reliability, observability, and maintainability
- Own the event-driven data layer — Kafka/Pub/Sub pipelines feeding AI workflows at scale
- Establish engineering standards for building reliable, secure, and auditable AI-powered systems across the team
- Influence technical strategy across teams and translate complex billing domain challenges into intelligent software solutions with measurable outcomes

What We're Looking For

- 8+ years of skilled software engineering experience building scalable distributed systems
- Mastery of Java and Spring Boot for high-throughput, cloud-native backend systems — this is the primary technical bar
- 2-3+ years of hands-on experience designing, shipping, and maintaining production AI-enabled applications combining LLMs, core application logic, and business workflows
- Practical experience with AI orchestration frameworks — LangGraph,



LangChain, LlamaIndex, or CrewAI — and deep understanding of RAG, tool calling, context and state management, and HITL patterns
- Strong background in distributed systems, event-driven architectures, asynchronous processing, and messaging platforms such as Kafka
- Python proficiency for AI/ML work specifically
- Proven experience implementing production AI safeguards: real-time observability, latency and cost monitoring, automated evaluation pipelines, and robust fallback mechanisms
- Cloud-native experience across AWS, Azure, or GCP

Preferred

- Healthcare IT, RCM, billing, claims processing, fintech, or similarly regulated, high-compliance domain background
- Experience building autonomous multi-step agentic systems with multi-tier memory and recursive reasoning
- Knowledge graph construction and enterprise vector search architecture
- PyTorch, HuggingFace Transformers, custom embedding models, or fine-tuning experience
- Past experience as a Founding Engineer, Principal Architect, or early-stage platform lead driving org-wide AI/ML adoption

Logistics

- Fully remote
- Canada-based candidates with work authorization only — placed through Syndesus as employer of record
- Base salary + benefits only; no bonus or equity in current EOR structure — generous salary raises twice yearly in lieu of bonus
- Comprehensive benefits (Sun Life, 100% family coverage) administered through Syndesus
- Unlimited PTO, 15-day minimum mandate

Compensation: $180,000-$220,000 CAD + Benefits

📌 Staff Software Engineer - AI Engineering (Canada)
🏢 Syndesus
📍 Canada