Engineering Engineering Manager, Automation Ontario

The technical challenge:

More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time‑consuming. , we are building the first mobile app to manage it all.

Our insurance marketplace is our core product today, and our ability to automate the end‑to‑end shopping experience is our core differentiator. The Marketplace Automation Team owns the most critical part of that, the "last mile", where we orchestrate complex, multi‑step transactions with external systems to finalize insurance policy purchases. Because the industry lacks modern APIs, we build custom orchestration layers that navigate internal and external interfaces with precision.

It is a high‑stakes puzzle of asynchronous state management and real‑time system reliability.

Your challenge will be to evolve our current automation systems to a robust, fault‑tolerant framework that can handle external interface changes gracefully and scale across dozens of new categories with minimal manual intervention.

• Ownership: You’ll report directly to our co‑founder/CTO, who is actively involved in product implementation. There is no red tape, no slow‑moving processes, and no layers of approvals needed. If you have an idea, you can pitch it, build it, and see it live in days.

• Stellar team: We have a very high bar for talent, as a result, we have a small but mighty team that can move fast and accomplish a lot. You will work with likeminded peers who are equally passionate and who care intensely about what they do.

• Hands‑on: Many of our TLMs are ex‑founders, they like getting their hands dirty and solving difficult problems. You will spend 80% of your time doing hands‑on technical work (e.g. transitioning our legacy automation systems into a more decoupled, scalable architecture).

• Volume of customer data: We are a consumer‑facing business (5M+ customers) and have access to a massive amount of customer data across behaviours like driving/telematics, shopping, payment, etc. which helps guide our product, technical and business decisions.

Our first automation system was built for speed, not scale. Today, it’s a web of tightly coupled business logic and database access that makes changes risky and failures hard to debug.

• Phase 1: You’ll be deep in the code, learning both the technical and business sides of our core product (insurance is very complex and every insurance provider uses different logic and behaves differently). Then you will lead incremental refactoring of our existing automation systems: designing and implementing new standards and pairing with engineers to ensure the new system is predictable and testable.

• Phase 2: As the architecture stabilizes, you’ll shift towards using an AI‑first approach to building the next generation of internal tools that will allow us to grow from 5M to 50M users.

• A Player Coach: You likely founded a company or were a lead architect at an early stage startup. You are a builder at heart and like being in the trenches alongside your team.

• A Detective: You are obsessed with success rates. You love hunting for edge cases in complex business logic and won't stop until you understand exactly why a script failed.

• A Systems Thinker: You have a high bar for system design, especially for offline, asynchronous jobs. You understand that async work requires much stricter standards for decoupling, state management, and failure retry logic than synchronous online systems.

Type Script (Nest.js, React), Graph

QL, AWS (ECS/EKS, Lambda).

While we appreciate your interest and application, only applicants under consideration will be contacted.

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