Senior Software Engineer (Remote - Toronto, Canada)

Contra

Location: Toronto, Canada
Job Type: full-time
Salary: $170,000 - $200,000 CAD
Posted: June 9, 2025

Job Description

Who we are and what we do

Contra is a multi-sided marketplace reinventing the future of work. We empower independents to build standout professional brands, get verified for their skills, and connect directly with top companies—without the friction of outdated hiring systems or commission fees.

For companies, Contra offers a flexible, all-in-one platform to discover, hire, and manage world-class independent talent. From onboarding to payments to collaboration, we make it seamless to work with freelancers across every stage of the project lifecycle.

We've raised over $44M from leading investors like NEA, Unusual Ventures, and Cowboy Ventures—and we're just getting started.

Why join Contra's journey?

We’re building the commission-free creative network. Think LinkedIn for creatives. We're laying the infrastructure for how the next generation works and earns.

At Contra, we believe the best work happens outside the constraints of traditional employment. With a network of over 1 million independents and 50,000 clients, we’re creating a new kind of professional network—one built on trust, transparency, and freedom.As work becomes more project-based and global, we’re helping top talent find meaningful opportunities, and helping companies scale with agility. If you’re excited about rethinking how people connect, collaborate, and thrive in the modern economy—this is the place to do it.

About You:

You understand modern AI systems, products and workflows. You have opinions and taste in these areas, and know how to build polished AI-driven user experiences that delight, not detract.
You are an excellent, independent problem solver.
You have high standards for craft, quality, and attention-to-detail for the work that you ship, and motivate others to raise the bar.
You know how to articulate and balance the tradeoffs of rapid pace exploration and building performant, scalable, reliable, and quality systems.
You have high standards for verbal and written communication and are experienced at working in a remote organization, preferring to over-communicate and collaborate synchronously when able.
You thrive in a fast-paced and dynamic environment. Our team knows how to execute and is relentless about our velocity. You smartly use AI to increase your personal velocity, but are experienced enough an engineer on your own to navigate and keep it in check.
You apply an ownership mentality to everything you ship, and collaborate cross-functionally with other teams to achieve success.
You dedicate effort to staying up to date with new technologies, patterns, and AI.

In a day at Contra, you’ll probably:

Contribute to our end-to-end TypeScript, GraphQL, React monorepo. You’ll work across the stack — including our AI stack (LLMs, embeddings, vector search, evals, etc.)
Contribute to our Vitest/Playwright test suite.
Participate in the RFC process, building alignment around new database and API schemas and new patterns.
Participate in all parts of the product development process, like design critiques, code reviews, and cross-functional planning with your team.
Work on maintaining a tidy home: eliminate technical debt, improve performance, address customer bugs, improve developer experience, etc.

Our Stack:

Backend: TypeScript, PostgreSQL, GraphQL, NodeJS, Redis, Temporal
Frontend: React, Relay, PandaCSS
Data: Airbyte, dbt, Google BigQuery
DevOps: ArgoCD, Docker, GitHub, Google Cloud Platform, Kubernetes
Testing: Playwright, Vitest
Tools: Linear, Mergify, PostHog, Slack, Turbo
AI: OpenAI, Cursor, Supermaven, CodeRabbit (for code reviews — it’s actually great!)

Total Comp:

Salary: $170,000 - $200,000 CAD
Health + dental benefits
Home Office Budget
We will provide you with a company laptop on your start date

Interview Process

Intro Call with Recruiting Team (15-20 minutes)
Technical Interview with Hiring Manager (45 minutes)
Culture & Cross-Functional Interview (45 minutes)
Paid Technical Assessment (3 hours) + Presentation (60 minutes)
1. CTO & Co-Founder
2. Engineering Manager
Interview with CEO & Co-Founder (30 minutes)

🎯 Who is this job for?

This role fits a Senior Software Engineer experienced in full-stack TypeScript and React development, with strong knowledge of GraphQL, Node.js, and scalable AI-driven systems. Candidates should be adept at working in fast-paced, remote environments, contributing across backend, frontend, and AI stacks, while emphasizing quality, performance, and collaboration. Familiarity with modern DevOps (Docker, Kubernetes, GCP) and testing frameworks (Vitest, Playwright) is essential.

💬 Potential Interview Questions

How do you build scalable AI-driven user experiences using React and TypeScript?
Design modular, performant components with React and manage complex state with tools like Relay; optimize rendering, handle async data via GraphQL, and integrate AI features (e.g., LLMs) responsibly to enhance UX.
What strategies do you use to maintain quality and reduce technical debt in a fast-paced remote team?
Implement strong testing (Vitest, Playwright), enforce code reviews, document RFCs for architecture decisions, refactor iteratively, and foster a culture of ownership and communication.
How do you balance rapid product exploration with building reliable and maintainable systems?
Use feature flags, iterative prototyping, scalable abstractions, performance monitoring, and prioritize tech debt alongside new features.
How do you design and evolve GraphQL schemas for complex, data-rich applications?
Engage in cross-team RFCs, maintain backward compatibility, modularize schema by domain, and use tools for schema validation and documentation.
What is your approach to testing in a monorepo with full-stack TypeScript and React?
Write unit tests with Vitest, end-to-end tests with Playwright, use mocks and fixtures, and automate testing in CI/CD pipelines to catch regressions early.
How do you apply AI and ML technologies effectively in a product workflow?
Integrate APIs like OpenAI thoughtfully, ensure outputs are contextually relevant, monitor model performance, and build user controls to guide AI features.
How do you ensure excellent cross-functional collaboration in a remote-first environment?
Over-communicate via synchronous and asynchronous channels, document decisions clearly, participate actively in planning and reviews, and foster a culture of trust and transparency.
Describe your experience with developer tooling and productivity enhancements in large codebases.
Use tools like Turbo for builds, code review assistants (CodeRabbit), linters, formatters, and invest in developer experience improvements to boost team velocity.
How do you manage data workflows involving tools like Airbyte, dbt, and BigQuery in a modern stack?
Coordinate data ingestion, transformation, and querying pipelines with clear contracts, automate deployments, monitor data quality, and align with product needs.
What motivates you to stay updated with evolving AI technologies and incorporate them into your engineering work?
Continuous learning through research, experimentation, community engagement, and a passion for applying AI to solve real-world user problems effectively and ethically.

📋 Job Summary

Contra is hiring a Senior Software Engineer in Toronto for a fully remote role with a salary range of CAD \$170K–\$200K. You'll work across a modern TypeScript, React, and GraphQL monorepo, contributing to AI-driven features, backend systems, and test suites. Join a fast-paced, innovative team building the future of freelance work with cutting-edge tech like LLMs, vector search, and Kubernetes. Enjoy top-tier benefits, a home office budget, and a culture of ownership and collaboration in a rapidly growing startup.