Tech Lead Manager, Automation

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As Tech Lead Manager, Automation at Jerry Technologies Inc., you will lead the evolution of the company’s core automation systems into a robust, fault-tolerant framework capable of handling external interface changes and scaling across dozens of new insurance and car ownership categories with minimal manual intervention. This role is critical to Jerry.ai’s mission of simplifying car ownership through AI-powered automation, directly impacting the experience of over 5 million customers by ensuring seamless, reliable end-to-end insurance policy purchases.
• You will spend 80% of your time in hands-on technical work, transitioning legacy automation systems into a decoupled, scalable architecture using TypeScript (Nest.js, React), GraphQL, and AWS (ECS/EKS, Lambda). Your day-to-day includes deep diving into complex business logic across diverse insurance providers, leading incremental refactoring efforts, designing new system standards, and pairing with engineers to ensure predictability, testability, and resilience in asynchronous, state-heavy workflows.
• You will report directly to the co-founder and CTO, operating in a high-ownership, low-bureaucracy environment where ideas can be pitched, built, and deployed live within days. You’ll join a small, elite team of ex-founders and builders who are intensely passionate about solving real-world problems through technical excellence and systems thinking.
• As the architecture stabilizes, you will lead the shift toward an AI-first approach to building next-generation internal tools that will enable Jerry.ai to scale from 5M to 50M users, leveraging the company’s vast customer data ecosystem (driving/telematics, shopping, payment behaviors) to inform product and technical decisions.
• You will grow as a systems thinker and player-coach, refining your ability to hunt edge cases in complex business logic, design fault-tolerant asynchronous systems, and mentor engineers through technical ambiguity — all while contributing to a product that is redefining a $1T+ industry and has already achieved #1 rating and 4.7 stars in the App Store.

🎯 Requirements

• Proven experience as a technical lead or founder/lead architect in an early-stage startup, with a track record of building and scaling complex automation or orchestration systems.
• Deep expertise in TypeScript, Nest.js, React, GraphQL, and AWS services (ECS/EKS, Lambda), with strong understanding of asynchronous job processing, state management, and fault-tolerant system design.
• Demonstrated ability to lead hands-on technical work while mentoring engineers, with a preference for candidates who thrive in high-ownership, low-process environments and enjoy getting ‘in the trenches’.

🏖️ Benefits

• Comprehensive health, dental, and vision coverage for regular employees.
• Paid time off, paid parental leave, and a 401(K) plan with employer matching.
• Equity grant opportunities as part of the total rewards package.
• Access to wellness benefits and the opportunity to work on a mission-driven product impacting over 5M customers.

Skills & Technologies

JavaScript

TypeScript

React

AWS

GraphQL

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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