Chief Software Architect

Masabi; Toronto; Remote; CAD 130,000 - 170,000; Full time

Job summary

A forward-thinking technology company in Toronto is seeking a Chief Architect to shape its multi-tenant SaaS platform strategy. The ideal candidate will drive architectural leadership, mentor engineers, and champion AI/ML adoption within the organization. This remote position welcomes applicants from Canada, encouraging innovation in a supportive culture. Discover a role where you can make an impact in the transportation technology sector.

Benefits

20 days vacation plus additional options

Private Healthcare

Training allowance up to CAD$1000

CAD$325 for home office setup

Enhanced family leave

Qualifications

• Proven experience leading architectural decisions for SaaS platforms.
• Excellent mentorship skills for senior engineers.
• Strong understanding of compliance standards (SOC2, ISO27001, PCI).

Responsibilities

• Define and evolve long-term architectural vision.
• Own architectural direction with a focus on AI and Data.
• Mentor and coach Principal Engineers for technical growth.

Skills

Hands-on technical leadership

Experience in distributed systems

Cross-functional collaboration

Passionate about AI/ML

Tools

Kotlin

TypeScript

Python

AWS

Job description

Overview

Introducing Masabi

At Masabi, we’re driving the fare payment revolution, powering the journeys of millions all over the world. We build fare collection platforms that allow riders to seamlessly buy and present tickets for public transport either on their mobile phones, from a ticket machine, or by tapping their bank card to travel.

Our Justride platform is used in over 250 locations globally, including some of the largest cities in the world. With our industry-first mobile ticketing SDK, we’ve partnered with large players in the transport space, including Uber, Moovit and Transit.

Your own journey is important to us too. Choosing a role here means joining a network of innovators from all walks of life; a group of passionate individuals who consistently deliver. Here, you’ll find the tools you need to build the career you want. Whether you’re taking the direct route or trying a new path, we’ll support you no matter what.

The Role

Masabi is hiring a Chief Architect, a collaborative, deeply technical and hands-on leader to shape our technology strategy, embed architectural standards and lead our Data and AI vision for our multi-tenant SaaS platform.

You’ll be Masabi’s key architectural partner, trusted for your clarity, technical insight, and ability to bring people with you. You’ll work across all levels of the organisation to ensure that our architecture supports scalability, resilience, security, and developer experience as we grow.

You’ll partner closely with the CPO and VP of Engineering to co-own strategic implementation, switching easily between 10,000-foot architecture and working in the codebase. You’ll lead our team of four Principal Engineers, supporting their growth, aligning them on technical direction, and fostering collaboration across squads and domains.

You’ll also champion thoughtful, responsible adoption of AI / ML capabilities, both as product features and to enhance developer workflows, embedding AI in ways that deliver meaningful value and long-term impact.

Location

This is a remote leadership role, only open to candidates based in Canada (Eastern Time Zone). Occasional travel may be required for planning sessions, strategic customer engagements, or team events.

Responsibilities

• Architectural Leadership
  • Partner with the VP of Engineering to define and evolve our long-term architectural vision, acting as the ultimate design authority while aligning with delivery priorities
  • Own the architectural direction of Masabi’s multi-tenant SaaS platform, with a strategic focus on AI and Data as innovation streams
  • Integrate and balance architectural direction, performance, compliance, and security into a single, outcome-oriented plan
  • Establish and embed architectural principles and participate in key design decisions to support alignment across teams
  • Promote best practices in system design, infrastructure design, reliability, observability, and performance
  • Stay actively engaged with code, tools, and infrastructure, leading through shared standards, not gatekeeping
  • Collaborate with product, engineering, and platform teams to de-risk decisions and enable confident delivery
• AI Enablement & Technical Innovation
  • Identify and nurture opportunities to embed AI / ML into our platform and engineering processes, ensuring value to customers and teams
  • Act as a supportive expert in Data and AI development, guiding standards, contributing to code, and enabling scalable, responsible implementation
  • Evaluate and recommend emerging tools and practices that improve scalability, reliability, and developer experience
  • Partner with Product and Engineering to develop a team that identifies and pilots AI-enabled capabilities that can be commercialised and scaled into the Masabi platform
• Technical Influence & Team Alignment
  • Collaborate with Product and Engineering leadership to align platform strategy with technical sustainability and scale
  • Mentor and coach Principal Engineers and other senior ICs, investing in technical leadership development
  • Partner with the VP of Engineering to ensure teams deliver against a coherent architecture, while maintaining agility and shared ownership
  • Foster a culture of inclusion, technical excellence, and sustainable delivery practices
• Security, Resilience & Compliance
  • Collaborate with platform and security teams to ensure alignment with compliance standards (SOC2, ISO27001, PCI)
  • Embed secure-by-design and fail-safe patterns across the platform
  • Strengthen operational awareness through instrumentation and observability tooling

Our Stack

At Masabi, we take a modern, pragmatic approach to technology, optimising for scalability, resilience, and developer experience.

• Kotlin (Backend & Mobile), TypeScript (Web), Python
• KrakenD & Ktor (APIs), Vue / Nuxt (Frontend), Capacitor (Hybrid Mobile)
• Fully cloud-hosted on AWS - Fargate, Lambda, DynamoDB, S3, SSM, KMS, etc.
• Kafka / Kafka Streams, DynamoDB as the primary store, limited use of Aurora
• GitLab CI / CD, Terraform & Terragrunt (IaC), Renovate (Dependencies)
• Grafana Cloud for metrics, logs, traces and SLOs; OpenTelemetry as our instrumentation standard
• Strong emphasis on meaningful tests at all levels of the testing pyramid
• AI tooling : JetBrains Junie, Amazon Q, Kiro, GitLab Duo, CodeRabbit, ChatGPT, Gemini, Microsoft Copilot

About You

• Hands-on, empathetic technical leader, experienced in distributed systems, platform-scale SaaS, and architectural ownership
• Someone who thrives in cross-functional environments and can communicate clearly with engineers, product managers, and commercial stakeholders alike
• Experience working in high-availability, regulated, or security-conscious environments
• Passionate about AI / ML and data-driven engineering, whether in product, tooling, or ops
• Mentored senior engineers and driven technical alignment in growing orgs
• Someone who leads with empathy, humility, and pragmatism

• Bonus Points
• Experience in fare payments, mobility, fintech, or embedded systems
• Exposure to M&A or platform re-architecture in scaling environments
• Contributions to open-source, architecture communities, or thought leadership

Benefits

• 20 days of vacation per year (plus option to buy 5 more); office shut Christmas–New Year for 28+ days total
• Private Healthcare and Life Insurance via Trinet
• Menopause support
• Choice of a workstation
• Training allowance up to CAD$1000 per year
• CAD$325 per year to spend on home office
• Ability to work up to 3 months per year from any country
• Enhanced family leave
• Careers at Masabi are for people going places - mission to make transit fair and accessible

Why Join Masabi?

• Driven by Purpose – journeys made simple
• Encouraged to Accelerate – you’re in the driving seat
• Advancing with Empathy – learning culture, no blame

We welcome applications from underrepresented backgrounds and encourage you to share your pronouns at any stage. Together, we simplify journeys, remove barriers, and improve daily life for millions.

Additional Note

Whoever you are, just be yourself. We’re intentional about our tooling and open to better ways of doing things; this role will shape where we go next.