About the Role

We're looking for a Senior Backend Engineer to architect the infrastructure that will scale us 25-30X over the coming months as we become the operating system for workplace mobility. As one of the first 10 engineers, you'll own critical systems handling millions of commuter transactions across hundreds of enterprise clients—potentially the largest transformation in urban transportation infrastructure since ride-sharing.

Why Now?

Three massive shifts are converging: companies are wrestling with return-to-office policies and need better commute solutions, new compliance and sustainability mandates are forcing mobility program changes, and employees expect seamless, intelligent benefits experiences. We're building the infrastructure layer for this transformation, and the next 12 months will define the category winner.

The backend challenges are significant and exciting. You'll be designing systems that need to handle real-time routing across multiple transportation modes, process high-volume financial transactions, manage complex enterprise integrations, and power AI-driven insights—all while maintaining the reliability and performance that enterprise customers demand. We're talking about building infrastructure that needs to be bulletproof at scale while shipping new capabilities weekly.

AI is central to our technical architecture. You'll be building the backend systems that power intelligent route optimization, predictive analytics for mobility patterns, and automated program management. We're integrating LLMs into production workflows in novel ways, which means designing APIs and data pipelines that support both traditional and AI-driven features. This isn't AI as a feature—it's AI deeply embedded in our infrastructure.

As product-driven engineers, we're committed to creating polished experiences while obsessing over the performance and reliability of what we build. We challenge the status quo and strive to find the best way to solve problems. We strongly follow the ship early and ship often strategy in almost everything we do. Instead of meticulously crafting the perfect product, we start at v0 and iterate towards the perfect vision. It's an ethos that's instrumental to our growth and one of our most cherished company practices in creating better work faster.

You'll work closely with the founding team and own large portions of our backend architecture. We're a small, exceptional team that moves fast and trusts each other completely. This role comes with meaningful equity—you're not just building infrastructure, you're building your own wealth alongside ours. This is a unique opportunity for someone who wants to be at the ground floor of a game-changing company with a clear path to technical leadership as we scale.

What You'll Be Doing (Responsibilities)

• Design and build scalable backend systems supporting millions of transactions across hundreds of enterprise clients
• Architect APIs and data models that power both customer-facing features and internal AI capabilities
• Build and optimize data pipelines for real-time routing, financial processing, and analytics at scale
• Implement caching strategies, database optimization, and service architecture to handle exponential growth
• Integrate and maintain AI/LLM capabilities in production, including prompt engineering and model management
• Set up observability, monitoring, and alerting systems to maintain reliability as we scale
• Establish engineering standards and processes as the company grows
• Provide technical feedback through code reviews, design reviews, and architectural decision-making
• Set a high bar for execution in both code quality and system reliability
• Hire, cultivate, and mentor new engineers as they join the team
• Join the founding team and be a part of all major future decisions

Whom We're Looking For (Requirements)

• 5+ years of backend engineering experience with proven ability to design and scale distributed systems
• Deep expertise in Python & Django REST or similar frameworks (Ruby on Rails, Java/Spring, Node.js)
• Strong track record shipping high-quality products in fast-moving environments
• Experience designing RESTful or GraphQL APIs that serve both web and mobile clients
• Proven ability to take ownership of large-scale backend systems from design through deployment
• Experience with relational databases (Postgres, MySQL) including query optimization and schema design
• Familiarity with caching strategies (Redis, Memcached) and when to apply them
• Experience building with AI tools like OpenAI, Anthropic, LangChain—integrating LLMs into production applications
• Strong background using git, version control, performing code reviews, and working in an agile environment
• Strong verbal and written communication skills for technical design discussions
• You're highly motivated, have a strong sense of ownership, and thrive in a fast-paced, dynamic work environment where you can take initiative and make things happen

Nice to Haves

• Familiarity with our tech stack (Python, Django REST, Postgres, Redis, AWS, Docker)
• Experience with frontend technologies (React, TypeScript) for full-stack contributions when needed
• Experience building fintech infrastructure: payment processing, transaction ledgers, financial reporting
• Previous experience at a transportation, mobility, or logistics company
• Background in DevOps and infrastructure: CI/CD pipelines, observability tools, container orchestration
• Experience with message queues, background job processing, and async workflows
• Knowledge of geospatial systems and routing algorithms
• Previous founding/startup experience or an itch to start a company in the future. We will invest in you!
• Experience in hiring and/or leading a team of highly motivated engineers
• Genuine excitement about equity ownership and being part of building something from the ground up

Tech Stack

• Backend: Python, Django REST API
• Database: Postgres, Redis
• Infrastructure: AWS, GCP, Docker
• AI/ML: OpenAI, Anthropic, LangChain
• Frontend: React, TypeScript (for context)
• Mobile: React Native, TypeScript (for context)

Location

Hybrid with 2-3 days per week in our Toronto office.