AI Engineer
Full time
Toronto (In-Person)
Join OpenSesame as an AI engineer to design and scale the backend behind our SMS-based AI agents, powering real customer and operational workflows across insurance, from quoting and underwriting to claims, renewals, and policy servicing.
Apply Here
For decades, insurance software has been built around rigid forms, portals, and call centers that create friction for customers and operational drag for teams. Even as AI has advanced, most insurance workflows are still manual, slow, and disconnected across systems.
At OpenSesame, we believe SMS is the most powerful interface for insurance. We are building AI agents that live directly in text messages and handle quoting, follow-ups, document collection, verification, claims intake, and broker communication. These agents connect directly to carrier, MGA, and broker systems, allowing insurance work to happen naturally, in real time, without forcing users into another portal.
We are looking for a founding AI engineer with a strong backend focus to help make this real. In this role, you will own core technical decisions from day one and design and scale the systems that power our SMS agents. You will build the infrastructure that handles conversation state, tool calling, policy and claims integrations, and the guardrails required to operate safely in regulated insurance environments.
You will work across the stack, but your primary responsibility will be the backend and AI engine that connects our agents to real customer data and production insurance systems. You will ship features that directly impact how brokers, underwriters, and customers interact with insurance every day, with a strong focus on reliability, accuracy, and performance at scale.
We are looking for a builder who thrives in high-autonomy environments, loves shipping quickly, and wants meaningful ownership in a fast-growing company that is working closely with real insurance partners.
Compensation is $120–200k plus equity, a new MacBook Pro, and more.
