Head of Software Engineering & Data

About Uride Technologies Inc.

At Uride, we're on a mission to empower underserved communities around the world by creating a marketplace that connects people in rural areas with essential services, starting with ridesharing. With operations in 25 cities across the country, Uride is Canada’s fastest-growing ridesharing company, providing over a million rides annually. Preparing for international expansion, our vision goes beyond transportation; we aim to become the leading platform for local entrepreneurs to launch service-based businesses, creating an ecosystem that benefits everyone.

By 2030, Uride will bring essential mobility – and beyond – to 1,000 cities, 10 million riders, and 100 million rides per year. To get there, Uride is scaling fast – and must evolve from scrappy to durable. We need a product-minded, seasoned engineering leader who turns customer problems into shippable solutions, measures impact, and builds the platform that powers growth. You’ll set the platform vision, build a high-performing team, and ship reliably, in quality and at high velocity.

Location: Toronto/Canada (hybrid, with in-office presence expected 2-3x/week)
Reports to: CEO
Partners with: Heads of Product & Operations

Your Mission

• Co-own Business Outcomes with Product. Define customer and business metrics (e.g., conversion, pickup ETA, trip success rate, cost/ride) and align the roadmap, architecture, and delivery plan to scale towards and beyond triple digit million CAN$ yearly revenue.
• Architect the Tech Strategy. Define the business capabilities needed, software selection (e.g. build/make vs. buy/rent) and own tech stacks for product delivery (i.e. OLTP) and company steering through data insights (i.e. OLAP).
• Shape the Platform Vision. Set the target architecture and a composable platform strategy that unlocks speed, reliability, and differentiating rider/driver experiences through innovative features.
• Drive Discovery to Delivery. Pair engineers with Product & Design in trios; run lightweight discovery, rapid prototyping, and A/B tests to de-risk bets (0..1) before scaling (1..10).
• Ship predictably. Establish clear intake, quarterly bets, design docs/ADRs, and a reliable release cadence tied to outcome metrics movement – not just output.
• Make reliability a feature. Stand up on-call, incident response, and end-to-end observability so customer experience improves alongside velocity.
• Modernize the Software Development Lifecycle (SDLC). Streamline architecture and infrastructure setup, adopt Infrastructure-as-Code (IaC), tighten CI/CD with quality gates and effective quality assurance and automated testing.
• Elevate engineering with AI. Deploy AI pair-programming, code search, and test generation across the SDLC (i.e. AI-assisted coding); auto-draft PR descriptions/reviews and release notes; use AI to keep docs/runbooks current and summarize incidents/postmortems; establish guardrails (i.e. prompt hygiene, PII protection, license/compliance); and track impact with DORA metrics (i.e. lead time, PR cycle time, MTTR, change failure rate) so rider/driver improvements ship faster.
• Raise the bar on Security & Data Privacy. Enforce secure SDLC, Role-Based-Access-Control (RBAC), secrets management, and GDPR-ready data practices as we expand.

• Impact: Measurable lifts in priority metrics (e.g., faster time-to-first-ride, improved p95 ETA, reduced failed trips, lower cost/ride).
• Delivery & Operations: End-to-end accountability for Product Delivery and Continuous Operations.
• Platform: Clear North Star for Engineering Strategy defined and approach laid out with tracked milestones; first critical services insourced with SLAs and dashboards for observability.
• Org: Domain ownership for software and data engineering in place; Engineering Culture Manifesto/Constitution defined; key leadership and individual contributor hires closed; pragmatic career paths and coaching loops active.
• Execution: Fewer context switches and less cognitive load for the tech team, visible Roadmap, stable iteration cadence; on-call with playbooks and blameless postmortems.
• SDLC: CI/CD with quality gates; IaC for core infra; improved test coverage on critical flows.

• Product-first Engineering Leadership. You’ve led software engineering and data in product companies (ideally in the mobility, marketplace or logistics space) and tie technical decisions to customer and revenue outcomes.
• Architecture & Platform depth. Pragmatic composable architecture transitions, clean service boundaries, API contracts, SLAs/SLOs, and cost-aware designs.
• Mobile & real-time systems. Comfort with mobile release trains (iOS/Android/React Native), push/telemetry, and low-latency eventing for live ops.
• Delivery excellence. Hands-on strategist and leader. You’ve implemented lightweight planning, ADRs/design docs, CI/CD with quality gates, and test automation strategies (unit/integration/e2e) that speed learning.
• Relentless Delivery Execution: You are in the details, uncompromising on accountability; clear and ambitious on expectations.
• Reliability as a feature. SRE habits – on-call design, incident command, blameless postmortems, observability/APM, and error budgets that protect customer experience.
• Data & Experimentation. Product analytics, event taxonomy, feature flags, A/B testing, and metric dashboards that inform roadmap and release decisions.
• AI-elevated Software Engineering. Hands-on with modern AI-assisted programming practices, quality safe guardrails, non-deterministic wire-fencing, etc.
• People leadership & org design. You hire and grow senior ICs/managers, shape clear domains/ownership and build Engineering Culture; you create psychological safety, establish a coaching culture and raise the bar.
• High EQ, low ego: You lead front and center, never from up and above; you can do the work of their team and show what good looks like.
• Make/build vs. bus/rent savvy. You’ve developed platform strategies with make and rent components and went through transitions effort (e.g., re-platforming), negotiated SLAs/DPAs, and sequenced insourcing without disrupting service delivery.
• Security, Data privacy & Compliance Literacy. Secure SDLC, RBAC, secrets management, SCA/vulnerability scanning; working knowledge of GDPR (and Canadian privacy norms) in production systems.
• Crisp Communication. Clear writing and exec-ready storytelling; you align cross-functional partners (Product, Design, Ops, CX) and keep the board/leadership outcome-focused.
• Tech Stack (nice-to-have): TypeScript/NestJS, React/React Native, Golang, GraphQL, AWS/serverless, Docker/K8s, Terraform/Pulumi, Snowflake/dbt, Metabase.

Compensation & Perks

• Competitive salary + performance bonus + meaningful long term incentives (i.e. equity)
• Freedom to own and shape your function and build your team in an upscaling tech business
• Travel to Uride markets and global launches and see your tech product in the real world
• Be part of a leadership team committed to co-ownership and operational excellence
• Partner directly with the CEO, fully committed to enabling your success