Skills
Backend engineering
AI engineering
AI agents
Conversation state management
Tool calling
Backend integrations
Production systems
System architecture
Reliability engineering
Scalable infrastructure
Regulated data workflows
Fast product development
Full-stack development
Python
Backend systems
LLM systems
SMS integrations
API integrations
Cloud infrastructure
Summary
A fast-growing insurtech is hiring a founding AI engineer with a strong backend focus to build the infrastructure behind conversational AI agents used in real insurance workflows. You will own major technical decisions, design systems for conversation state, tool calling, enterprise integrations, and safety guardrails, and work across the stack while focusing primarily on backend and AI infrastructure. This is a high-autonomy opportunity for a builder who enjoys rapid shipping, deep ownership, and solving reliability and scalability challenges in a regulated industry. The role includes meaningful equity and founding-team-level influence.
Highlights
Founding-level ownership, significant influence over core technical decisions, meaningful equity, direct impact on real customer workflows, high autonomy, and the opportunity to build and scale AI infrastructure from the ground up.
Description
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.
