Tech Lead Manager, 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 Jerry’s legacy insurance policy purchase system, which currently relies on tightly coupled business logic and direct database access that introduces risk and complexity.
• Own the end-to-end orchestration of asynchronous, multi-step transactions with external insurance provider systems that lack modern APIs, requiring custom integration layers to navigate inconsistent, undocumented interfaces with precision and reliability.
• Serve as a hands-on technical leader, spending 80% of your time writing code, reviewing architecture, and pairing with engineers to refactor legacy systems into decoupled, testable, and observable components using TypeScript, Nest.js, and GraphQL.
• Drive incremental refactoring of core automation workflows, establishing new standards for state management, retry logic, and error handling to ensure system resilience during external provider outages or schema changes.
• Act as the primary architect for transitioning from a brittle, manual-heavy system to an AI-first internal tooling platform capable of scaling from 5M to 50M users by automating detection, adaptation, and recovery from external system inconsistencies.
• Deeply understand the complex, provider-specific business logic governing insurance underwriting, quoting, and policy issuance across dozens of carriers, each with unique rules, data formats, and failure modes.
• Investigate and resolve edge cases in transaction failures with forensic precision, tracking root causes from external API timeouts to malformed data payloads, and designing systematic fixes to prevent recurrence.
• Collaborate directly with the co-founder/CTO to prioritize technical initiatives, propose new architectures, and ship features rapidly without bureaucratic delays—ideas can be built and deployed within days.
• Build and maintain high-availability systems processing millions of customer interactions daily, leveraging AWS services including ECS, EKS, and Lambda to ensure real-time reliability under unpredictable load patterns.
• Use massive, real-world customer data (telematics, payment, shopping behavior) to inform system improvements, prioritize technical debt, and validate the impact of architectural changes on user outcomes.
• Mentor junior engineers by modeling best practices in system design, asynchronous workflow management, and observability, fostering a culture of ownership and technical excellence.
• Transition from hands-on development to strategic leadership as the system stabilizes, focusing on building autonomous tools that reduce manual intervention in maintaining integrations with new insurance carriers and product categories.
• Champion system reliability metrics, obsessing over success rates and failure modes, and implementing automated alerts, logs, and dashboards to provide full visibility into orchestration health.
• Collaborate across product, data, and compliance teams to ensure automated workflows align with regulatory requirements and customer experience goals in the heavily regulated insurance industry.
• Represent the Core Backend Team in cross-functional planning, translating technical constraints into product roadmaps and identifying opportunities to automate previously manual processes across Jerry’s ecosystem.

🎯 Requirements

• Proven experience as a technical leader or founding engineer in a high-growth startup with ownership over core backend systems handling high-volume, mission-critical transactions
• Deep expertise in designing and maintaining asynchronous, stateful systems with robust retry, failure recovery, and decoupling strategies—especially in environments with unreliable or undocumented external APIs
• Strong proficiency in TypeScript, Node.js (Nest.js), GraphQL, and AWS services (ECS, EKS, Lambda)
• Demonstrated ability to refactor legacy, tightly coupled codebases into modular, testable, and observable architectures
• Obsession with system reliability, success rates, and debugging complex edge cases in business logic
• Experience working in highly regulated industries (e.g., insurance, finance) with complex, provider-specific rulesets

🏖️ Benefits

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

Skills & Technologies

JavaScript

TypeScript

React

AWS

GraphQL

Backend

Senior

Onsite

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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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