Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
May 26, 2026
Full Job Description
📋 Description
- • Lead the design and implementation of a robust, fault-tolerant automation framework to replace legacy systems that orchestrate complex, multi-step insurance policy purchases across heterogeneous external provider systems with no modern APIs.
- • Spend 80% of time in hands-on technical work: refactoring tightly coupled business logic and database access into a decoupled, testable, and scalable architecture using TypeScript (Nest.js), GraphQL, and AWS services (ECS/EKS, Lambda).
- • Own the ‘last mile’ of customer transactions — the critical system layer where asynchronous state management, retry logic, and real-time reliability determine success rates for policy finalization.
- • Deeply understand complex insurance industry workflows, where each provider has unique rules, data formats, and failure modes, and build systems that can adapt to these variations with minimal manual intervention.
- • Lead incremental migration of existing automation systems by establishing new coding standards, conducting code reviews, and pairing with engineers to ensure predictability, observability, and debuggability of mission-critical workflows.
- • Design and implement AI-first internal tools to scale the platform from 5M to 50M+ users, leveraging massive customer behavioral datasets (telematics, payment, shopping, etc.) to automate decision-making and reduce dependency on manual configuration.
- • Act as a Player-Coach: directly contribute to high-impact technical decisions while mentoring engineers, fostering a culture of ownership, and maintaining a high bar for system design and reliability.
- • Investigate and resolve edge cases in business logic with detective-like precision — tracing failures through asynchronous workflows, external system timeouts, data mismatches, and state inconsistencies.
- • Build systems with strict standards for offline job handling, including idempotency, state snapshots, dead-letter queues, and automated retry cascades that exceed those of typical synchronous online systems.
- • Collaborate directly with the co-founder/CTO with no red tape; propose, build, and ship technical solutions within days without layers of approval or bureaucracy.
- • Work alongside a small, high-performing team of ex-founders and senior engineers who are deeply invested in solving hard technical problems and moving fast with minimal overhead.
- • Evolve the Core Product Engine to support expansion into new vehicle-related categories beyond insurance — such as financing, maintenance, and safety services — while maintaining system integrity and automation fidelity.
- • Ensure all systems are observable, well-documented, and monitored for performance, error rates, and transaction success metrics across diverse external provider environments.
- • Translate complex insurance business rules into executable, automated workflows that are resilient to external system changes, vendor API deprecations, and data schema drift.
🎯 Requirements
- • Proven experience as an Engineering Manager or Lead Developer in a high-growth startup or early-stage company with ownership of mission-critical backend systems
- • Deep hands-on expertise in building and refactoring asynchronous, stateful automation systems using TypeScript (Nest.js) and AWS services (ECS/EKS, Lambda)
- • Strong systems thinking with expertise in designing fault-tolerant, decoupled architectures for offline/async workflows with rigorous failure recovery and retry logic
- • Experience navigating complex, legacy business logic with no standardized APIs, particularly in regulated industries like insurance or financial services
- • Demonstrated ability to lead technical refactoring efforts while maintaining system reliability during high-traffic, customer-facing operations
- • Obsessive attention to detail in debugging edge cases and optimizing success rates in multi-system transaction workflows
🏖️ Benefits
- • Health, dental, and vision coverage
- • Paid time off and paid parental leave
- • 401(k) plan with employer matching
- • Wellness benefits
- • Equity grant opportunities
- • Direct reporting to co-founder/CTO with rapid decision-making and minimal bureaucracy
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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