Principal Software Engineer

toronto, on, Canada • Posted June 13, 2026

Job Type: Full-time
Location: toronto, on
Posted: June 13, 2026
Category: Other-General
Application Deadline: July 23, 2026

Role Description

Our mission? To power measurable employee engagement worldwide. And we’d love for you to join us!

About the job - Principal Software Engineer

ContactMonkey's platform already runs AI in production - AI-powered template editing, a standalone ConfidenceCheck service that evaluates outgoing emails for editorial quality and link safety, Braintrust-backed evaluations, and per-organization feature gating. The next wave is bigger: grounded assistants, retrieval over customer brand and campaign history, richer agentic flows inside the composer, and data products that make sending decisions smarter.

We're forming a dedicated AI pod to own that trajectory. With the team you will be setting the technical direction for the pod, make the foundational infrastructure bets (vector store, evals, data warehouse, agent orchestration), and ship the first production systems yourself. AI is a major thrust, and the Principal Engineer will set technical direction across this work — ...

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