Engineering Team Lead, Core Product Engine (Backend)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• Lead the design and implementation of a scalable, fault-tolerant automation framework to replace the current tightly coupled legacy system managing end-to-end insurance policy purchases across dozens of external providers with no standardized APIs.
• Serve as a hands-on technical leader, spending 80% of your time writing code, refactoring critical systems, and pairing with engineers to ensure new architecture adheres to strict standards for decoupling, state management, and retry logic in asynchronous workflows.
• Own the core "last mile" of the product: orchestrating complex, multi-step transactions between Jerry’s platform and external insurance carrier systems, ensuring reliability despite inconsistent, non-standardized interfaces.
• Diagnose and resolve failures in production automation scripts by deeply investigating edge cases in business logic unique to each insurer’s proprietary workflows, treating each failure as a puzzle to be fully solved.
• Transition existing automation systems from a monolithic, high-risk codebase into a modular, testable, and observable architecture using TypeScript (Nest.js), GraphQL, and AWS services including ECS/EKS and Lambda.
• Pioneer the development of AI-first internal tools that enable automated adaptation to external system changes, reducing manual intervention as the platform scales from 5M to 50M users.
• Collaborate directly with the CTO and engineering team to rapidly prototype, test, and deploy new features without bureaucratic delays—ideas move from concept to live in days.
• Drive technical decisions around system reliability, observability, and scalability, with a focus on offline, asynchronous processes that require higher rigor than synchronous online systems.
• Deeply understand the complexities of the U.S. auto insurance industry, including insurer-specific rules, data formats, and state-by-state compliance nuances, to build accurate and resilient automation logic.
• Mentor engineers by setting examples in code quality, debugging discipline, and architectural thinking, while maintaining an egoless, collaborative team culture.
• Analyze customer behavior data (driving/telematics, payment patterns, shopping behavior) to inform technical improvements and prioritize automation enhancements with the highest customer impact.
• Maintain ownership of system uptime and success rates for policy purchase completions, where even small failure rates directly impact customer trust and business revenue.
• Document architectural changes, failure modes, and resolution patterns to institutionalize knowledge and reduce onboarding time for new team members.
• Evaluate and introduce new tools or patterns that improve system resilience, reduce technical debt, and increase team velocity without compromising reliability.

🎯 Requirements

• Proven experience as a hands-on technical leader in early-stage startups or as a founder, with a track record of building and refactoring complex backend systems under pressure.
• Deep expertise in designing and maintaining asynchronous, stateful automation systems with robust retry logic, fault tolerance, and observability, particularly in high-stakes transactional environments.
• Strong proficiency in TypeScript, Nest.js, and AWS services (ECS/EKS, Lambda) for building scalable backend services.
• Demonstrated ability to debug and resolve failures in complex, multi-party business logic with inconsistent external interfaces, treating edge cases as critical puzzles.
• Experience working with non-standardized, legacy, or proprietary third-party systems where APIs are absent or unreliable.
• Passion for system design with an obsession for reliability, success rates, and reducing manual intervention through automation.

🏖️ Benefits

• Health, dental, and vision coverage
• Paid time off
• Paid parental leave
• 401(k) plan with employer matching
• Wellness benefits
• Equity grants as part of total compensation

Skills & Technologies

JavaScript

TypeScript

React

AWS

GraphQL

Backend

Senior

Onsite

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

Jerry Technologies Inc.

Visit Website

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.

View Company Profile

Get more remote jobs like this

Subscribe to the weekly newsletter for similar remote roles and curated hiring updates.

Weekly remote jobs and featured talent.

No spam. Only curated remote roles and product updates. You can unsubscribe anytime.