Lead, Rating and AI Systems

remote
Toronto, ON, Canada .
full-time . December 16, 2025

Description

About Rival

Rival Insurance Technology is building Canada’s next-generation insurance platform, powered by an AI-native engineering approach, modern data architecture, and deep domain expertise. We’re reinventing how brokers, carriers, and MGAs work by accelerating development through AI-native tooling, knowledge extraction from legacy systems, and rapid product iteration.

To compete with billion-dollar incumbents, we don’t just build software — we build the technology that builds the software.

 The Role

We’re looking for a senior technical leader to transform Rival’s Rating platform into an AI-native, agent-driven system. This role combines deep insurance rating expertise, hands-on AI engineering, and technical leadership to modernize how rating logic is designed, governed, and delivered.

This role is approximately 70% hands-on technical leadership and 30% strategy, coaching, and change management. We are fully remote across Canada.

You will design the frameworks, rule models, and AI-assisted tools that allow rating logic to be generated, validated, and deployed at unprecedented speed — including by non-developers.

 What You Will Do

AI & Rating Architecture

Design and build AI-powered, agentic rating pipelines using frameworks like LangChain, CrewAI, or similar.
Orchestrate end-to-end rating workflows, from data ingestion to final rating output.
Develop prompt engineering and RAG pipelines grounded in proprietary rating logic, actuarial data, and regulatory documentation.
Act as Human-in-the-Loop (HITL) to validate AI-generated code for accuracy, security, and compliance.
Embed AI into CI/CD pipelines for automated testing, validation, and documentation.

Rating Logic & Automation

Lead the design of manufactured rating and structured rule frameworks.
Translate regulatory filings, underwriting rules, and actuarial logic into deterministic, AI-readable formats.
Define a low-code / DSL framework that allows safe, compliant rule updates by non-engineers.
Drive automation across testing, regression detection, calculations, and comparisons.
Help drive our evolution toward daily rating releases, with a focus on reducing manual code through automation.

Strategy, Leadership & Change

Contribute to the roadmap for transitioning the Rating team to AI-native workflows.
Champion AI adoption and coach teams on prompt engineering, agent governance, and verification.
Set performance metrics tied to AI-augmented productivity and quality.
Partner closely with Product, Engineering, Data, Regulatory, and AI teams.
Model our values, including innovation, experimentation, and rapid learning.

 What You Bring

Domain Expertise

Strong background in personal lines rating (Auto or Property).
Knowledge of underwriting rules, risk classification, FSRA/provincial regulations, and CSIO standards.

Technical Skills

Experience with C# / .NET, APIs, enterprise systems, and CI/CD.
Experience modeling logic using JSON, rules engines, decision tables, or declarative systems.
Familiarity with low-code or DSL-based systems (nice to have).

AI & Leadership

Hands-on experience with LLMs, RAG, agentic workflows, and prompt engineering.
7+ years of software development experience, including senior or lead roles.
Experience building AI or automation systems in regulated environments.
Strong communicator who can explain complex logic to technical and non-technical audiences.
Curiosity, energy, and the ability to lead teams through change.

Background

Bachelor’s or Master’s degree in Computer Science, Data Science, or a related quantitative field or experience.
7+ years of software development experience.
2+ years of hands-on experience architecting and deploying AI / LLM-based systems in production.
Experience working in regulated domains (insurance, finance, healthcare) with strong audit requirements.
Background in personal lines rating (Auto or Property).
Expertise with agentic frameworks (LangChain, AutoGen, CrewAI).
Strong understanding of LLM fundamentals (RAG, prompt optimization, governance).
Experience with cloud-native development and MLOps platforms (AWS, Azure, or GCP).
Strong background in CI/CD, DevOps, and Agile delivery.
Demonstrated success delivering complex systems while building healthy, high-performing teams.

Why Join Rival

Build Canada’s first AI-native insurance rating platform
Work directly with leadership to define the future of Broker Management Platforms
Move faster than any legacy vendor or startup
Zero bureaucracy — maximum impact
A mission that actually matters to the industry

Know someone who would be a perfect fit? Let them know!