Tech Lead Manager, Distributed Systems

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As Tech Lead Manager for Distributed Systems at Jerry Technologies Inc., you will lead the evolution of the company’s core automation infrastructure, transforming a tightly coupled, legacy system into a robust, fault-tolerant framework capable of scaling across new product categories with minimal manual intervention. This role is critical to Jerry.ai’s mission of simplifying car ownership through AI-powered automation, as the backend orchestration layer you will own directly enables the end-to-end insurance purchasing experience that differentiates the platform in a fragmented, outdated industry.
• You will spend approximately 80% of your time in hands-on technical work, diving deep into the existing TypeScript-based automation systems built with Nest.js, GraphQL, and AWS services (ECS/EKS, Lambda), while guiding a small but elite team of engineers through incremental refactoring, architectural modernization, and the introduction of AI-first internal tools. Your leadership will ensure the system evolves from a fragile web of coupled logic into a predictable, testable, and scalable platform capable of handling asynchronous state management and real-time reliability demands.
• You will report directly to the co-founder and CTO, operating in a high-autonomy, low-bureaucracy environment where ideas can be pitched, built, and deployed to production within days. This direct access to executive leadership empowers you to influence both technical direction and product strategy, leveraging insights from 5M+ customer data points spanning driving behavior, telematics, payments, and shopping patterns to inform system design and prioritization.
• You will lead Phase 1 of the transformation: deeply understanding the complex, provider-specific logic of the insurance domain while refactoring legacy automation systems into decoupled, standards-driven components. In Phase 2, you will shift focus to architecting AI-powered internal tools that will enable Jerry.ai to scale from 5 million to 50 million users, blending systems thinking with emerging AI capabilities to future-proof the platform.
• You will join a small, high-caliber team of ex-founders and senior builders who prioritize technical excellence, ownership, and egoless collaboration. The team operates with intense passion and a shared commitment to solving hard problems, creating an environment where craftsmanship, curiosity, and relentless improvement are valued over process or hierarchy.
• In this role, you will develop deep expertise in distributed systems design, asynchronous workflow orchestration, and AI-augmented tooling, while honing your ability to lead technical teams through ambiguity and change. You will gain visibility into how a high-growth consumer tech company leverages data and automation to disrupt legacy industries, positioning you to drive impact at the intersection of engineering, product, and AI innovation.

🎯 Requirements

• Proven experience as a technical leader or lead architect in early-stage startups or founder-led environments, with a track record of building and scaling complex backend systems from the ground up.
• Deep expertise in TypeScript, Nest.js, GraphQL, and AWS (ECS/EKS, Lambda), with hands-on experience designing and operating distributed, asynchronous systems at scale.
• Strong systems thinking mindset, particularly around decoupling, state management, failure recovery, and retry logic in offline or asynchronous job processing environments.

🏖️ Benefits

• Comprehensive health, dental, and vision coverage for employees and dependents.
• 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.
• Direct access to co-founder/CTO and a high-autonomy, innovation-driven culture with minimal bureaucracy.
• Opportunity to work with a small, elite team of ex-founders and senior builders on a mission-critical product impacting 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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