Chief Software Architect

myGwork - LGBTQ+ Business Community; Toronto; Remote; CAD 120,000 - 150,000; Full time

Job summary

A leading technology firm is seeking a Chief Software Architect for a remote leadership role. The successful candidate will drive technology strategy, embed AI/ML capabilities, and lead a team of Principal Engineers. Applicants should have a strong background in distributed systems and SaaS, with empathy and leadership skills. The position offers competitive benefits including vacation days, healthcare, and a collaborative work environment.

Benefits

20 days vacation + 5 optional buy

Private Healthcare and Life Insurance

Training allowance up to CAD$1000/year

CAD$325/year for home office

Enhanced family leave

Qualifications

• Experience with distributed systems and platform-scale SaaS.
• Ability to mentor and align technical teams.
• Familiarity with security and compliance standards.

Responsibilities

• Define and evolve architecture for scalability and resilience.
• Identify opportunities for AI/ML integration.
• Collaborate with security teams for compliance.

Skills

Hands-on technical leadership

Strong communication

Experience in AI/ML

Empathy in leadership

Tools

Kotlin

Python

TypeScript

AWS

GitLab CI/CD

Job description

Overview

Overview Join to apply for the Chief Software Architect role at Masabi. This is a remote leadership role based in Canada (Eastern Time Zone) with occasional travel. Masabi is an inclusive employer and a member of myGwork – the largest global platform for the LGBTQ+ business community.

Masabi is driving the fare payment revolution with the Justride platform, powering journeys in over 250 locations worldwide. You will shape technology strategy, embed architectural standards, and lead the Data and AI vision for a multi-tenant SaaS platform. You will work closely with the CPO and VP of Engineering, lead a team of four Principal Engineers, and champion AI / ML capabilities across products and developer workflows.

Location: Remote leadership role (Canada Eastern Time Zone). Occasional travel may be required for planning sessions, strategic customer engagements, or team events.

Note: This job is with Masabi, an inclusive employer and a member of myGwork. Please do not contact the recruiter directly.

Responsibilities

• Architectural Leadership: Define and evolve Masabi2f to ensure scalable, resilient, secure architecture; align with delivery priorities; act as the ultimate design authority.
• AI Enablement & Technical Innovation: Identify opportunities to embed AI / ML into the platform and engineering processes; guide standards and enable scalable, responsible implementation.
• Technical Influence & Team Alignment: Align platform strategy with technical sustainability and scale; mentor Principal Engineers and senior ICs; ensure coherent architecture with agile, shared ownership.
• Security, Resilience & Compliance: Collaborate with security teams to meet compliance standards (SOC2, ISO27001, PCI); embed secure-by-design patterns; strengthen observability.

Technical Stack & Approach

• Kotlin (Backend & Mobile), TypeScript (Web), Python
• APIs: KrakenD & Ktor; Frontend: Vue / Nuxt; Hybrid Mobile: Capacitor
• AWS: Fargate, Lambda, DynamoDB, S3, SSM, KMS; Kafka / Kafka Streams; DynamoDB as primary store
• CI / CD: GitLab CI / CD, Terraform & Terragrunt, Renovate; Observability: Grafana Cloud, OpenTelemetry
• Testing: meaningful tests across the testing pyramid; AI tooling including JetBrains Junie, Amazon Q, Kiro, GitLab Duo, CodeRabbit, ChatGPT, Gemini, Copilot

About You

• Hands-on, empathetic technical leader with experience in distributed systems, platform-scale SaaS, and architectural ownership
• Strong communicator across engineers, product managers, and commercial stakeholders
• Experience in high-availability, regulated, or security-conscious environments
• Passionate about AI / ML and data-driven engineering
• Mentored senior engineers and driven technical alignment in growing organizations
• 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 or architecture communities

Benefits

• 20 days vacation + 5 days optional buy; closed for Christmas–New Year (28+ days)
• Private Healthcare and Life Insurance
• Menopause support
• Choice of workstation; training allowance up to CAD$1000 / year
• CAD$325 / year for home office; remote work up to 3 months / year from any country
• Enhanced family leave; collaborative environment focused on making a difference

Careers at Masabi are for people going places — driven by a mission to make transit fair and accessible for all. We welcome applications from underrepresented backgrounds and encourage you to share your pronouns. We simplify journeys, remove barriers, and improve daily life for millions.

Why Join Masabi?

• Driven by Purpose — journeys made simple; the work is challenging but rewarding
• Encouraged to Accelerate — opportunities to grow and explore new paths
• Advancing with Empathy — people-first culture with shared responsibility

We are already powering journeys — are you ready to join us?

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