Location Hybrid – Downtown Toronto (Nucleus @ MaRS Waterfront, 155 Queens Quay E) The Opportunity: Automating the Dental Economy InsideDesk builds the infrastructure that powers revenue flow across the North American dental market. We operate at the intersection of real-world financial workflows, large-scale data systems, and applied AI, where reliability and correctness matter. Dental revenue remains trapped inside outdated insurance portals, inconsistent remittance formats, and manual reconciliation workflows.

We build production systems that retrieve, parse, and reconcile millions of claims for Dental Service Organizations (DSOs) and clinics. We are entering a growth phase through 2026 and expanding our engineering team with senior engineers who want to build durable systems that operate in the real world. The Role & What You’ll Work On As a Senior Software Engineer on the Application Team, you will design and operate revenue-critical backend systems and serve as a technical anchor for a 5-person team.

You’ll work on infrastructure shaped by messy real-world data, volatile external systems, regulatory constraints (HIPAA / SOC 2), meaningful data scale, and AI operating under cost, security, and reliability constraints. This is not a ticket-execution role. Senior engineers shape architecture, drive trade-offs, and own system behavior end-to-end.

We expect you to think in systems, not features, and to make architectural decisions that stand up to real operational pressure.

Core Backend

Systems - Design and evolve services built in Python (Flask) and PostgreSQL





- Optimize queries and data models handling hundreds of millions of records
- Build background processing and job orchestration layers
- Deploy and operate services on AWS (ECS/Fargate, serverless workloads) Applied AI in Production - Integrate LLM-based parsing into real revenue workflows
- Design fallback logic and observability around AI pipelines
- Ensure AI systems meet cost, security, and compliance requirements
- Define how deterministic systems and agentic components interact safely and predictably in production This is applied AI under real production constraints, not demo-driven experimentation.

Technical

Ownership - Drive architectural decisions and system design

- Own systems through implementation and operational health
- Mentor engineers and uphold high code quality standards Ownership includes operational responsibility. When systems break or degrade, we fix and improve them deliberately.

What You

Bring - 5+ years building backend systems (Python preferred)

- Robust PostgreSQL and relational data modeling experience
- Experience optimizing performance at meaningful data scale
- Background processing / job orchestration experience




- Strong Linux/Unix fundamentals and cloud experience (AWS preferred)
- Secure coding practices You are comfortable making decisions under ambiguity and favor simple, durable solutions over unnecessary complexity.

Why This

Role - Serious Systems : Revenue-critical infrastructure used daily by real customers.

- Production AI : AI embedded into core workflows with observability, cost controls, and compliance discipline.
- Ownership : Architectural influence and end-to-end responsibility.
- Meaningful Scale : Millions of claims. Hundreds of millions of records. Real performance trade-offs.
- High-Standard Environment : Clear architectural bar. Bias toward simplicity, durability, and operational excellence. We hire deliberately and prioritize depth and judgment. This role is for engineers who care deeply about system quality, prefer solving reliability problems over building demos, thrive with autonomy and accountability, and want to build systems that must work, even when the real world behaves unpredictably. Culture & Interview Process Hybrid by Design Expect 1 – 3 days per week in our downtown Toronto office. High-bandwidth design conversations matter.

Practical

Process - Intro conversation with engineering leadership

- Live paired-coding session based on real-world problems
- In-person system design discussion
- We focus on practical signals, not LeetCode-style puzzles. Nice to Have - Exposure to React (
- Experience in Healthcare, FinTech, or RCM systems

📌 Senior Software Engineer – Application Team (Burlington)
🏢 Socket.dev
📍 Burlington