Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
May 26, 2026
Full Job Description
đź“‹ Description
- • Lead the design and implementation of a scalable, fault-tolerant automation framework to replace Jerry’s legacy insurance policy purchase system, which currently relies on tightly coupled business logic and direct database access.
- • Deeply own the "last mile" of end-to-end insurance transactions, orchestrating complex, asynchronous workflows across external insurer systems with no standardized APIs, requiring custom integration layers for reliability and precision.
- • Conduct hands-on refactoring of existing codebases to decouple business logic from data access, introducing standardized patterns for state management, retry logic, and failure recovery in high-stakes, offline processing pipelines.
- • Serve as both technical lead and individual contributor, spending approximately 80% of time writing, reviewing, and debugging production code alongside engineers, with direct reporting to the co-founder/CTO.
- • Diagnose and resolve edge cases in insurance provider-specific logic, where each carrier uses unique rules, data formats, and response behaviors, requiring meticulous detective work to ensure 99.9%+ transaction success rates.
- • Design and implement AI-first internal tools to enable automated handling of new insurance categories and external system changes, reducing manual intervention as Jerry scales from 5M to 50M users.
- • Collaborate with cross-functional teams to understand the full insurance purchase workflow, including underwriting rules, payment processing, and policy binding logic across dozens of U.S.-based insurers.
- • Maintain and evolve a technical stack built on TypeScript (Nest.js, React), GraphQL, and AWS services including ECS/EKS and Lambda, ensuring system observability, monitoring, and performance optimization at scale.
- • Drive adoption of testable, predictable architectures by pairing with engineers to review designs, enforce code quality standards, and document system behavior for long-term maintainability.
- • Own end-to-end system reliability for customer-facing transactions where failures directly impact user trust, policy validity, and revenue, requiring rigorous attention to data consistency and auditability.
- • Contribute to technical strategy by identifying bottlenecks in current automation, proposing architectural improvements, and prioritizing initiatives based on impact, risk, and scalability.
- • Leverage access to 5M+ customer datasets — including telematics, payment behavior, and shopping patterns — to inform technical decisions that improve system performance and user experience.
- • Participate in high-velocity product development cycles with no bureaucracy, where ideas can be pitched, built, and deployed live within days.
🎯 Requirements
- • Proven experience as a hands-on technical lead or architect at a high-growth startup or early-stage company, with ownership of mission-critical backend systems.
- • Deep expertise in building and maintaining asynchronous, offline workflows with robust state management, retry logic, and failure recovery mechanisms in cloud environments (AWS).
- • Strong proficiency in TypeScript and Node.js frameworks (e.g., Nest.js), with experience in GraphQL and serverless architectures (Lambda, ECS/EKS).
- • Demonstrated ability to refactor legacy, tightly coupled systems into decoupled, scalable, and testable architectures under high reliability constraints.
- • Obsessive attention to edge cases in complex business logic, especially in domains with non-standardized external integrations (e.g., insurance, finance, logistics).
- • Track record of leading engineering teams in high-stakes, consumer-facing environments with millions of users and real-time transactional reliability requirements.
🏖️ Benefits
- • Equity grants as part of total compensation package.
- • Comprehensive health, dental, and vision insurance coverage.
- • Paid time off and paid parental leave.
- • 401(k) plan with employer matching.
- • Wellness benefits.
- • Opportunity to work directly with co-founder/CTO in a fast-paced, high-autonomy environment with no layers of approval.
About Jerry Technologies Inc.
Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.
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