Engineering Manager, Core Product Engine (Backend)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As an Engineering Manager for the Core Product Engine (Backend) at Jerry Technologies Inc., you will lead the evolution of the company’s critical automation systems that orchestrate end-to-end insurance policy purchases, a high-stakes, complex workflow involving asynchronous state management and real-time reliability due to the lack of modern APIs in the industry.
• You will spend 80% of your time in hands-on technical work, leading the refactoring of tightly coupled legacy systems into a decoupled, scalable architecture, while guiding the team through incremental improvements and setting new standards for predictability and testability.
• You will report directly to the co-founder/CTO in a flat, fast-moving organization with no bureaucratic layers, enabling rapid iteration and direct impact, where ideas can be built and deployed in days.
• You will join a small, high-caliber team of ex-founders and builders who are deeply passionate about solving complex problems, and you will leverage access to rich customer data from 5M+ users to inform technical and product decisions.
• In Phase 1, you will deepen your understanding of the insurance domain and lead the refactoring of legacy automation systems; in Phase 2, you will drive an AI-first approach to build next-generation internal tools to scale the platform from 5M to 50M users.
• You will act as a player-coach, working alongside engineers in the trenches, applying your systems thinking to improve decoupling, state management, and retry logic for asynchronous jobs, while hunting down edge cases in complex business logic to improve success rates.
• The tech stack includes TypeScript (Nest.js, React), GraphQL, and AWS (ECS/EKS, Lambda), and you will help shape its evolution to support long-term scalability and reliability.

🎯 Requirements

• Proven experience as a founder, lead architect, or senior technical leader in an early-stage startup environment with a builder mindset.
• Strong systems thinking expertise, particularly in designing fault-tolerant, asynchronous, and decoupled systems with rigorous state management and retry logic.
• Hands-on proficiency with TypeScript, Nest.js, GraphQL, and AWS services (ECS/EKS, Lambda) to lead technical work and guide architecture decisions.
• Ability to deeply understand complex business domains (e.g., insurance logic across providers) and translate them into reliable, maintainable technical solutions.
• Track record of leading incremental refactoring efforts to improve system predictability, testability, and scalability without disrupting ongoing operations.

🏖️ Benefits

• Comprehensive health, dental, and vision coverage for regular employees.
• Paid time off, paid parental leave, and a 401(K) plan with employer matching.
• Wellness benefits and access to equity opportunities as part of the total rewards package.
• Opportunity to work directly with the co-founder/CTO in a high-autonomy, low-bureaucracy environment where impact is immediate and visible.
• Access to a rich dataset from 5M+ customers to drive data-informed technical and product decisions.
• Chance to work with a small, elite team of ex-founders and passionate builders who prioritize egoless collaboration and solving real-world problems.

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Jerry Technologies Inc.

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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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