Jobs in Canada

Senior Technology Leadership Professional in Canada

507 active opportunities · Updated October 2026

Explore current senior technology leadership professional jobs across Canada. Filter by work mode, employment type, experience, department, date posted and distance.

O
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listingCompany trend -63.6%

From C$136K/yr

Quick readStrong listing-quality and freshness signals

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. The Agent Gateway Team The Agent Gateway team owns the identity-aware infrastructure that connects enterprise AI agents to the tools, data, and services their organizations authorize. Every call from Claude, Agentforce, Codex, and internal/homegrown agents to a resource flows through us. We enforce authorization, isolate credentials, mint the right token per target, and produce the audit trails that security teams rely on. We are early in a rapidly evolving space. The standards for agent identity (MCP, OAuth token exchange, DCR) are being built under our feet. Our roadmap includes hardening the data plane for on-premises customer deployments, extending policy semantics beyond tool-level allowlists, adding native support for Agent-to-Agent brokered delegation, and scaling to tenants with thousands of virtual MCP servers. The Senior Software Engineer Opportunity Okta is looking for a Senior Software Engineer to help build the Agent Gateway. You will own features and components across the data and control planes, turning technical designs and product requirements into reliable production systems. Working alongside staff engineers, you will implement token exchange, request routing, credential resolution, and policy evaluation as agent identity specifications evolve. This is a hands-on software development role at the intersection of product, security, and infrastructure. You will ship services that handle agentic traffic reliably and performantly at scale. Wha

JavaAWSRestMachine Learning
R
📍 Toronto, Canada· Full-time
✓ High-confidence listingCompany trend -76.2%
Quick readStrong listing-quality and freshness signals

Join us in building the future of finance. Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading. About the team + role We are building an elite team, applying frontier technologies to the world's biggest financial problems. We're looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn't a place for complacency, it's where ambitious people do the best work of their careers. We're a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards. The Developer Infrastructure org is the engine behind Robinhood's entire engineering organization — a collection of tightly integrated teams whose collective mission is to make every engineer at Robinhood faster, more reliable, and exponentially more productive. The org spans four major teams: DevX (Developer Experience), TestX (Test Infrastructure), Backend Platform, and Mobile Platform. DevX owns Robinhood's monorepo and Bazel-based build infrastructure — the critical layer between a developer writing code and that code being ready to ship — along with the company's full CI/CD pipeline and remote build execution cluster. TestX owns the infrastructure behind Robinhood's entire test experience: the integration test environments, and personal development environments that serve as miniature simulations of the full Robinhood system, giving engineers a safe, isolated space to test their code end-to-end before it ever touches production. Backend Platform and Mobile Platform own the core language runtimes, libraries, IDEs, and developer toolchains across Python, Go, TypeScript, Swift, and Android. Together, these teams share a single north star: leveraging AI and agentic systems

TypeScriptPythonAWSKubernetes
O
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listingCompany trend -63.6%

C$108K – C$135K/yr

Quick readStrong listing-quality and freshness signals

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. This is a contract position through our staffing partner Magnit. 108,000.00 - 135,000.00 - 162,000.00 CAD Annual This role is not eligible for the Okta-sponsored benefits listed below. Magnit will provide any locally required benefits. Okta seeks a skilled Senior Recruiter to drive full-lifecycle recruitment and build strategic talent pipelines for our Engineering organization across North America. As part of our AMER Tech Recruiting team, you will be a trusted talent advisor responsible for sourcing, engaging, and delivering top-tier engineering talent while maintaining an "always recruiting" mindset in a fast-paced, high-growth environment. What You'll Be Doing Own full-lifecycle recruitment for Engineering and technical roles (Software Engineering, Site Reliability, Security, TPM, Product) across US & Canada, managing a flexible req load that scales with business priorities. Partner strategically with hiring managers and leadership to understand talent needs, define role scope, advise on talent gap mitigation, and challenge assumptions to ensure hiring decisions strengthen long-term organizational capability. Build and execute talent strategies that balance external hiring with internal mobility, creating sustainable pipelines that reflect commitment to diversity, inclusion, and high-performing engineering culture. Drive metrics-informed recruiting decisions by developing KPIs, analyzing recruiting data, and using insights to optimi

AWSRestMachine LearningAI
O
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listingCompany trend -63.6%

From C$118K/yr

Quick readStrong listing-quality and freshness signals

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. The role At Okta, we believe AI will fundamentally transform how design, research, and product development happen. We are looking for a Senior Design Operations Program Manager, Agentic Design to lead the operationalization and enablement of internal AI agents, plug-ins, and automated workflows across our Design team — reimaging how designers create in the AI era through internal AI agents. In this role, you will bridge the gap between AI tooling capabilities and practical design ops execution. You will partner closely with design, product management and design systems to govern, evaluate, deploy, and scale AI-driven design capabilities — making our 60+ person design org dramatically faster, more consistent, and highly innovative. This is a tactical, execution-focused builder role for an operations leader who is deeply curious about AI tools, understands modern UX workflows, and excels at change management, team enablement, and operationalizing new frameworks. What you'll do AI & Agentic Design Enablement Serve as the operational connective tissue driving AI adoption, evaluation, and workflow integration across Product Design, UX Research, and Content Design. Manage the intake, evaluation, and approval process for design plug-ins, Model Context Protocol (MCP) integrations, and generative AI tools (e.g., custom content design assistants, design-to-code agents). Partner with internal engineering teams to operationalize, ship, and drive adopt

AWSRestMachine LearningAI
L
📍 Toronto, Canada· Full-time
✓ High-confidence listingCompany trend -73.4%

From C$136K/yr

Quick readStrong listing-quality and freshness signals

At Lyft, our purpose is to serve and connect. We aim to achieve this by cultivating a work environment where all team members belong and have the opportunity to thrive. Our Infrastructure team is passionate about building software to solve problems at massive scale. We do this often, and when we believe our solution is worth sharing with the community, such as Envoy Proxy , we open source our ideas for the benefit of others. As a Infrastructure Engineer at Lyft, you will run our Production Infrastructure by monitoring system availability and take a holistic view of our platform health. You will build software and platforms to automate infrastructure platform operations and management. By measuring and monitoring our operations you will seek opportunities to optimize our systems in order to push our platform forward, anticipating our customers' needs in order to continually improve the platform. You will provide Lyft partner teams with operational support to help them build robust large scale distributed systems. About the Team Data Pipelines is at the heart of all critical data flowing through Lyft supporting hundreds of services that impact millions of drivers and passengers every day. Our team’s mission is to empower Lyft engineers to self-serve in building and maintaining data pipelines as needed to support products that deliver the world’s best transportation experience. We leverage a variety of technologies to store, stream and manage data making it available to our internal customers. Responsibilities: Maintain and analyze metrics from; operating systems; control planes; and applications to assist in fault detection and performance enhancement Design, develop and deploy tooling and systems that continually improve the reliability, scalability and efficiency of our platform Balance feature development speed and reliability with service-level objectives Operate and improve our Infrastructure using industry best practices and tools Participate in design and

PythonAWSDockerKubernetes
U
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listing
Quick readStrong listing-quality and freshness signals

Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond. Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn , Facebook , Instagram , TikTok , and X ; and learn more about Lifted at Go-Lifted and follow on LinkedIn . As a Senior People Operations Specialist, you will play a key role in delivering thoughtful, scalable people programs and operational support across the employee lifecycle. As part of our People Operations team, you’ll combine strong operational expertise with the judgment and partnership skills needed to support HR Business Partners, managers, and employees through both day-to-day needs and more complex people matters. You’ll own and continuously improve key people programs and processes, with a particular focus on employee lifecycle operations, immigration

Machine LearningAIGoRust
O
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listingCompany trend -63.6%

From C$136K/yr

Quick readStrong listing-quality and freshness signals

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. Senior Software Engineer, Device Identity Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are, too, let's talk. Device Identity and Access Organization The Device Identity and Access organization is at the forefront of Okta’s Zero Trust vision. As a foundational pillar within Okta Research and Development (ORD), our mission is to transform the device itself into a secure, trusted, and effortless identity factor. We are the teams responsible for ensuring users can seamlessly interact with their work from any endpoint, anywhere in the world. We engineer the end-to-end device experience—from our flagship FastPass , Okta Device Access (ODA), and Device Assurance . Our teams own the continuous authentication pipeline, device lifecycle management, and the sophisticated cloud services that analyze real-time trust and assurance signals to make frictionless, passwordless access a reality across Windows, macOS, iOS, Linux and Android. Our organization is comprised of engineers who thrive at the intersectio

JavaReactSQLMySQL
O
📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listingCompany trend -63.6%

From C$108K/yr

Quick readStrong listing-quality and freshness signals

Secure Every Identity, from AI to Human Identity is the key to unlocking the potential of AI. Okta secures AI by building the trusted, neutral infrastructure that enables organizations to safely embrace this new era. This work requires a relentless drive to solve complex challenges with real-world stakes. We are looking for builders and owners who operate with speed and urgency and execute with excellence. This is an opportunity to do career-defining work. We're all in on this mission. If you are too, let's talk. Role Overview As the Okta Research & Design (ORD) Jira Owner & Administrator , nested within the Technical Program Management (TPM) organization, you will define and execute the strategy for how ORD plans, tracks, and reports on engineering work within the full toolchain of Atlassian Jira, Jira Advanced Roadmaps (Plans), Confluence, Rovo, and AI integrations. In this role, you act as a critical bridge between product & technical leadership, agile teams, and cross-functional business units — translating methodology, best practices, and process frameworks into practical workflow improvements that accelerate delivery and reduce manual overhead for a 1,000+ person engineering, product, and design organization. By optimizing tooling configurations, automating reporting, and eliminating fragmented management processes, you will directly accelerate ORD’s developer velocity and strengthen operational efficiency. Core Responsibilities 1. Platform Ownership & Strategic Tooling Direction Strategic Vision: Define, implement, govern an AI-led strategy for utilizing Jira for product planning, tracking, and reporting tooling that supports end-to-end portfolio tracking from high-level corporate objectives down to sprint-level stories. E2E Ecosystem Management: Complete ORD ownership of the toolchain (Jira, Jira advanced Roadmaps, AI integrations, Confluence), overseeing architecture, schema updates, workflow management, screen/notification schemes, cu

SQLAWSCI/CDGit
R
📍 Toronto, Ontario, Canada· Full-time· Remote
✓ High-confidence listingCompany trend -80%

From $10K/yr

Quick readStrong listing-quality and freshness signals

About Ramp Ramp is building the smart infrastructure for finance teams, embedded in the transaction flow of every dollar a business spends. We automate how over $200B in annualized spend flows in and out of 70,000+ companies: authorizing payments, flagging risk, categorizing spend, and closing books. The problems are high-stakes, data-dense, and unforgiving. We hire people with high agency and high urgency. We look for slope over intercept. We care less about where you trained and more about what you’ve built. At Ramp, everyone is a builder who owns problems end to end and makes consequential decisions that shape the outcome. The median Ramp customer saves 5% and grows revenue 16% in their first year – far in excess of businesses operating without Ramp. We believe every ambitious company deserves the same. If you want to build systems that directly shape how companies move and manage billions, Ramp is the place to do it. About the Role As the founding Channel Partner Manager for Canada, you will build the partner motion that helps Canadian businesses discover, evaluate, and adopt Ramp through trusted advisors and ecosystem partners. This is a zero-to-one role. You will own the full partner lifecycle, from identifying and engaging Canadian accounting, advisory, private equity, and venture capital partners through signing, enablement, activation, and partner-sourced pipeline. Your early results will help determine how Ramp scales its Canadian channel motion. You will work closely with Sales, Growth, Product, Engineering, and the broader Partnerships organization. The right person is a hands-on builder: equally comfortable opening a new relationship, running a partner meeting, solving an operational blocker, and turning early learnings into a repeatable playbook. What You’ll Do Build Ramp’s Canadian channel strategy and operating rhythm from the ground up. Research, identify, source, qualify and sign net-new Canadian partners. Create joint go-to-market and activation p

RestAIGoRust
O
📍 Canada· Full-time· Remote
✓ High-confidence listingCompany trend -100%
Quick readStrong listing-quality and freshness signals

About the Team OpenAI’s User Operations team ensures that our customers' experience is nothing short of exceptional. We resolve complex issues, provide guidance, and support customers in maximizing value with our products. Within User Operations, Ads Safety Operations helps OpenAI grow advertising in a way that is safe, trusted, and sustainable for advertisers, users and the business. The Ads Safety Support team sits within Ads Safety Operations and owns the advertiser-facing support journey: helping advertisers navigate ads products, policies, reviews, and enforcement decisions while turning frontline insights into better guidance, tooling, and product experiences. About the Role We’re looking for a Senior Advertiser Support Specialist to help build and scale advertiser support within Ads Safety Operations. You’ll work directly with advertisers through support tickets, escalations, owning high-impact questions related to ads policies, review outcomes, product behavior, and operational processes. Many cases will be novel or ambiguous, and you’ll be expected to investigate carefully, communicate clearly, and drive them to resolution in a fast-moving product environment. As OpenAI’s advertising ecosystem grows, your work will help advertisers operate successfully at scale while serving as a critical bridge between frontline support and the teams responsible for product quality, policy integrity, and platform safety. Beyond resolving individual cases, you’ll help define what world-class support looks like in an AI-native environment. You’ll turn support interactions into operational intelligence, identifying recurring friction, gaps in guidance, and emerging issues to improve support at scale, and protect the quality and safety of OpenAI’s ad ecosystem. You’ll partner closely with Engineering, Product, Policy, Legal and Go To Market partners to improve systems, reduce bugs, and elevate the customer experience, while leveraging automation, agents, and our own AI technol

PythonAWSRestAI
G
📍 British Columbia, Canada· Full-time
✓ High-confidence listingCompany trend -100%

From C$107K/yr

Quick readStrong listing-quality and freshness signals

Location Details: At GoDaddy the future of work looks different for each team. Some teams work in the office full-time; others have a hybrid arrangement (they work remotely some days and in the office some days) and some work entirely remotely.​ Remote: This is a remote position, so you’ll be working remotely from your home. You may occasionally visit a GoDaddy office to meet with your team for events or meetings. About the Team Global Compute builds and operates the core cloud infrastructure that engineering teams rely on every day. We provision and manage AWS accounts across the company, operate the network backbone that connects them, and maintain the security guardrails that keep those environments safe, compliant, and scalable. We believe reliability is an engineering challenge, not an operations task. We automate repetitive work, build for scale before it becomes a problem, and invest heavily in observability to identify issues before they impact the business. What you'll get to do... Operate and scale AWS production infrastructure, owning the health of services that provision, secure, and manage accounts across GoDaddy AWS organisations. Design, build, and maintain cloud platform capabilities using Python, CloudFormation, AWS CDK, and automation-first practices. Drive cost optimisation initiatives that improve efficiency and deliver measurable business impact. Improve observability through monitoring, alerting, dashboards, and operational tooling. Participate in on-call rotations, lead incident response efforts, and drive long-term reliability improvements through blameless post-incident reviews. Support strategic AWS initiatives across networking, identity, governance, and multi-account architecture. Review code and designs, contribute documentation and operational runbooks, and mentor fellow engineers. Leverage AI-assisted tooling to improve engineering productivity, accelerate automation, and reduce operati

PythonAWSCI/CDGit
R
📍 Toronto, Canada
✓ Quality checkedCompany trend -76.2%

Join us in building the future of finance. Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading. About the team + role We are building an elite team, applying frontier technologies to the world's biggest financial problems. We're looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn't a place for complacency, it's where ambitious people do the best work of their careers. We're a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards. The Core Infrastructure team's mission is to build and evolve the foundational platform that every Robinhood engineering team builds on — owning the systems, primitives, and developer-facing abstractions that power 24/7 trading, crypto, and global expansion. We treat infrastructure as a product: reliable, fast to provision, and invisible to the teams above it. As a Senior Staff Software Developer on Core Infrastructure, you will own the architectural evolution of three deeply interconnected domains: service mesh and connectivity, compute platform, and infrastructure provisioning. Your decisions will directly shape engineering velocity, operational reliability, and Robinhood's ability to expand to new regions and markets. This is not an operations role — it's a once-in-a-platform-lifecycle opportunity to redesign the foundation before complexity becomes permanent! This role is based in our Toronto, ON office, with in-person attendance expected at least 3 days per week. At Robinhood, we believe in the power of in-person work to accelerate progress, spark innovation, and strengthen community. Our office experience is intentional, energizing, and designed to fully support high-p

PythonKubernetesArtificial IntelligenceAI
R
📍 Menlo Park, CA· Full-time
✓ Quality checkedCompany trend -76.2%

Join us in building the future of finance. Our mission is to democratize finance for all. An estimated $124 trillion of assets will be inherited by younger generations in the next two decades. The largest transfer of wealth in human history. If you’re ready to be at the epicenter of this historic cultural and financial shift, keep reading. About the team + role We are building an elite team, applying frontier technologies to the world's biggest financial problems. We're looking for bold thinkers. Sharp problem-solvers. Builders who are wired to make an impact. Robinhood isn't a place for complacency, it's where ambitious people do the best work of their careers. We're a high-performing, fast-moving team with ethics at the center of everything we do. Expectations are high, and so are the rewards. The Load and Fault team sits within Robinhood's Developer Infrastructure organization, with a mission to give every engineering team the tools they need to test their services under real-world conditions before those conditions test them in production. We build the platforms and frameworks that enable load testing, fault injection, and resilience validation at scale — treating reliability as a developer productivity problem, not just an operations one. Our work directly raises the quality bar for every service Robinhood ships, and we partner closely with engineering teams across the organization to make resilience testing a seamless part of the development workflow. As a Senior Software Engineer on the Load and Fault Environments team, you will design and build the infrastructure that lets Robinhood's engineers simulate load, inject faults, and validate system behavior under stress — at the scale of a fast-growing financial platform. You'll own meaningful components of the load testing and fault injection platform, write production-quality code, and collaborate with engineers across infrastructure and product teams to ensure the tooling you build gets adopted and drives real

PythonVueAWSKubernetes
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