Jobs in Canada

Lead Enterprise Systems Engineer in Toronto

142 active opportunities · Updated October 2026

Explore current lead enterprise systems engineer jobs in Toronto. Filter by work mode, employment type, experience, department, date posted and distance.

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📍 Toronto, Ontario, Canada
✓ High-confidence listingCompany trend -65.7%
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. Position Description: You will proactively construct and own an AI-forward research roadmap for key product pillars at Okta, operating at the intersection of Identity, Security, and Artificial Intelligence. As a Staff-level individual contributor, you will drive both qualitative and quantitative methodologies to define user experiences for non-deterministic AI agents, automated workflows, and enterprise platforms. Additionally, you leverage agentic tools and AI workflows internally to scale qualitative coding, synthesis, and research operations across the organization. In this role, you’ll get to: Drive Product-shaping Research: Lead foundational and evaluative research to inform strategic and tactical product decisions. Execute Balanced Mixed-Methods: Drive qualitative depth (contextual inquiry, cognitive walkthroughs) and quantitative rigor (large-scale surveys, behavioral telemetry, statistical modeling) to evaluate AI products. Pioneer AI Research Operations: Integrate AI tools, prompt engineering, and agentic research workflows into your daily practice to accelerate quality research outputs. Lead Cross-Discipline Collaboration: Facilitate research to drive cross-discipline clarity, executive alignment, and decision-making across complex security and admin workflows. Solve Complex Problems: Bring stakeholders together across multiple teams to scope problems and collaborate on research in ways that nurture a culture of curiosity and learning. Cultivate E

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

About Forma.ai: Forma.ai is a Series B startup that's revolutionizing how sales compensation is designed, managed and optimized. We handle billions in annual managed commissions for market leaders like Edmentum, Stryker, and Autodesk. Our growth has been fuelled by our passion for fundamentally changing and shaping how companies use sales intelligence to drive business strategy. We’re welcoming equally driven individuals who are excited about creating something big! Director, SPM Implementation About the Team The Customer Operations team partners with new and existing customers to implement and optimize the company’s platform, ensuring clients maximize the revenue-driving potential of their sales compensation programs. The team leads complex implementations, drives operational excellence, and continuously evolves Sales Performance Management (SPM) processes through data-driven insights and scalable platform solutions. As a Director of Implementation , you will lead the strategic direction of implementation and customer onboarding across a portfolio of enterprise customers. You will oversee implementation teams, guide architectural design of customer solutions, and collaborate closely with Product, Engineering, and Revenue teams to ensure the platform evolves in alignment with customer needs and business priorities. If you’re passionate about building high-performing teams, driving customer impact through data and technology, and shaping the future of sales operations , we’d love to hear from you. What You'll Be Doing Leadership & Strategy Define and lead the implementation strategy and operational framework for onboarding and scaling customer deployments. Build, mentor, and lead a high-performing implementation team , establishing best practices, processes, and standards for delivery excellence. Partner with executive leadership to align customer implementation strategy with company growth and product roadmap priorities . Establish KPI

RestAIGoExcel
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📍 Toronto, Canada· Full-time
✓ Quality checkedCompany trend -91.7%

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team As a platform company powering businesses all over the world, Stripe processes payments, runs marketplaces, detects fraud, helps entrepreneurs start internet businesses from anywhere in the world, builds world-class developer-friendly APIs, and more. The engineering teams at Stripe work on the business logic for all of that. As a software engineering manager at Stripe, you'll lead teams that build and expand APIs, services, and experiences. You'll also work with partners to launch new markets and vertical capabilities. Stripe Terminal helps our users extend their online presence to the physical world. The mission of the Terminal team is to make it as easy for businesses to accept in-person payments as the Stripe API has done for online payments—building for Unified Commerce. With Terminal, businesses can unify their in-person and online experiences, unlocking payments use cases that are right for their business model—whether it's creating a modern retail experience, extending their website to a pop-up store, or enabling a mobile point-of-sale at their next event. Within Terminal, the Commerce team focuses on the following to help make Unified Commerce a reality for businesses across the globe. Enterprise features—on-reader forms, tipping, gift cards Payment features—DCC, surcharge, multi-capture Point-of-sale integrations—enterprise-focused integrations Low-code and no-code—solutions that will enable our users to onboard quickly What you'll

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📍 Toronto, Ontario, Canada· Full-time
✓ Quality checkedCompany trend -100%

Who Are We? Postman is the world’s leading API platform, used by more than 45 million+ developers and 500,000 organizations, including 98% of the Fortune 500. Postman is helping developers and professionals across the globe build the API-first world by simplifying each step of the API lifecycle and streamlining collaboration—enabling users to create better APIs, faster. The company is headquartered in San Francisco and has offices in Boston, New York, Austin, Tokyo, London, and Bangalore - where Postman was founded. Postman is privately held, with funding from Battery Ventures, BOND, Coatue, CRV, Insight Partners, and Nexus Venture Partners. Learn more at postman.com or connect with Postman on X via @getpostman. P.S: We highly recommend reading The "API-First World" graphic novel to understand the bigger picture and our vision at Postman. The Opportunity We are looking for a Key Account Director to lead growth within a set of Postman’s most important enterprise accounts. This role is part of a new strategic go-to-market motion designed to deepen our engagement with large enterprises, expand our footprint, and deliver the full value of the Postman platform. You will be paired with a pod that includes a Principal Solutions Engineer and a Field CTO, forming a high-caliber account team focused on building long-term, value-based relationships. Together, you’ll engage senior technology leaders, uncover complex challenges, and drive adoption of Postman’s enterprise and platform solutions at scale. This is not a traditional “low-hanging fruit” sales role—this is about strategic account expansion, multi-threaded enterprise engagement, and solution selling. Location: This is a fully remote position. What You’ll Do Own and grow a portfolio of strategic enterprise accounts (e.g., Fortune 500, cloud-first companies, large-scale developer organizations). Deeply engage with senior buyers—CIOs, CTOs, VPs of Engineering, Platform, Security, and Collaboration—to position Postm

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📍 Toronto, Ontario, Canada· Full-time
✓ Quality checkedCompany trend -91.7%

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team Stripe's Financial Connections group is building technology that expands the scope of problems we tackle beyond card payments. We aspire to enable individuals and businesses to securely share their financial data to improve their product experiences. With more high-quality customer financial data, both Stripe and our users can offer better products to their customers. We have ambitious goals to enable all global businesses to run their entire financial life cycle on Stripe, and we want you to be part of our story. Technical Operations roles in Financial Connections are a dynamic and critical component of the organization's success. As Financial Connections TechOps Manager, you will lead a team of Integration Reliability Engineers who sit at the intersection of product and platform engineers, financial partners, and AI automation. Your role is to ensure that nothing is lost in translation: setting the standard for how the team operates, where it invests, and how the operational backbone of Stripe's open banking ecosystem stays reliable at scale. What you'll do Lead integration reliability and partner operations Own the health of Financial Connections' banking integrations at the team level—define what "reliable" looks like across the partner ecosystem, set the operational bar, and hold the team to it Serve as the management escalation point for complex partner issues, coordinating across financial partners, Stripe engineering, and product lea

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📍 Toronto, Canada· Full-time
✓ Quality checkedCompany trend -91.7%

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The Billing organization at Stripe builds and operates Stripe Billing, a growing product vertical inside of Stripe. Hundreds of thousands of businesses of all sizes and types use Stripe Billing to collect revenue for recurring and one-time payments across a variety of different pricing models—from selling SaaS subscriptions, to orchestrating multi-stage contracts, delivering business analytics, and providing recovery and retention tools to prevent customer churn. To support even the most unique and complex business models, our technology and products must be configurable and programmable. This requires our team to innovate in how we model different types of businesses, and how we use technology to enable customers to piece together Stripe’s Billing’s platform primitives into holistic solutions that support any type of business. Through this work, Stripe Billing allows worry-free innovation and evolution of any customer’s business model. Stripe is defining the industry’s approach to Billing solutions; we’re looking for innovators to join us. What you’ll do We’re looking for an experienced Engineering Manager to lead a team within the Stripe Billing organization. In this role, you will manage a high-performing team of engineers and partner closely with product managers and other cross-functional leaders to shape the team’s strategy and roadmap. You will excel in this role if you’re a product-focused engineering manager who can collaborate effe

O
📍 Toronto, Ontario, Canada
✓ High-confidence listingCompany trend -65.7%
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. Okta Workflows is the secure, no-code automation platform that empowers organizations to build identity-centric workflows across cloud applications — all without writing code. Our intuitive drag-and-drop interface allows enterprises to automate complex business processes at scale, enhancing productivity, enforcing security, and simplifying IT operations. Customers like Netflix, MGM, and NTT rely on Workflows to automate high-impact identity scenarios with speed and confidence. As we continue to scale, we’re investing in extensibility, developer experience, and performance. Join us to help shape the future of cloud automation and low-code development. Position Description We’re hiring a Staff Full-Stack Engineer to join the Integration Builder team within Okta Workflows. This team owns the core no-code surface that enables both internal teams and third-party developers (ISVs) to build powerful integrations and automation experiences with ease. As a Staff Engineer, you’ll lead initiatives that span front-end and back-end services — delivering performant, secure, and scalable features. You’ll help define architecture, drive implementation, and collaborate closely with Design, PM, and Platform teams. You’ll also work directly with our technical architects to help shape what we build — and how we build it. This is a high-impact role in a growing, strategic product area with strong executive visibility. Role Details: Design, build, and maintain end-to-end feature

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📍 Toronto, Ontario, Canada
✓ High-confidence listingCompany trend -65.7%
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 We are looking for a Principal Product Manager to lead the strategic evolution of the Auth0 Platform Infrastructure. In this highly visible, high-impact leadership role, you will be the visionary force behind the core infrastructure, consumption models, and platform capabilities that power Auth0’s immense global scale. You will own the multi-year strategy for critical platform pillars, with a heavy emphasis on redefining our rate-limiting and platform consumption frameworks. As a Principal product leader, you will navigate multi-dimensional scaling challenges (including the paradigm shift of autonomous AI agents), influence executive stakeholders, and ensure our platform remains the most resilient, secure, and performant identity solution for the world’s largest enterprises. What You’ll Do Drive the Long-Term Platform & Consumption Strategy: Define and own the multi-year roadmap for Auth0’s core infrastructure. Align deeply technical platform architecture with broader business objectives, Go-To-Market strategies, and overarching revenue goals. Spearhead the Strategic Evolution of Rate Limits & Monetization: Transform rate limits from a protective mechanism into a core business strategy. Pioneer dynamic consumption models, proactive policy-aware observability, and intelligent throttling strategies that align platform costs with customer value, reduce escalations, and unlock new SKUs. Architect Global Cloud Resilience & Scale: Champion ov

AWSAzureGCPMachine Learning
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📍 Toronto, Ontario, Canada· Full-time
✓ Quality checkedCompany trend -65.7%

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. Okta enables universal, secure access to technology for every user and organization. The Device Identity and Access team ensures that every endpoint interacting with corporate resources is trusted, healthy, and secure. Our pillar spans four domains: Device Identity, Device Authentication, Device Security Posture, and Endpoint AI Security. We are hiring a Product Manager to drive our Zero Trust Authentication group. In this role, you will lead the core execution, performance, and deployment strategy for Okta’s foundational endpoint products. You will own the operational excellence of Okta Verify , FastPass , and Device Assurance , ensuring that our core passwordless authentication flows and device posture engines remain performant, secure, and incredibly easy for global enterprises to deploy at scale. This is a critical, high-impact role designed for a highly autonomous product manager. Y

AWSLinuxRestMachine Learning
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📍 Toronto, Canada
✓ Quality checkedCompany trend +10%

Our Purpose Mastercard powers economies and empowers people in 200&#43; countries and territories worldwide. Together with our customers, we’re helping build a sustainable economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation, partnerships and networks combine to deliver a unique set of products and services that help people, businesses and governments realize their greatest potential. Title and Summary Lead Data Scientist Overview: Services within Mastercard is responsible for acquiring, engaging, and retaining customers by managing fraud and risk, enhancing cybersecurity, and improving the digital payments experience. We provide value-added services and leverage expertise, data-driven insights, and execution. The Cyber and Intelligence Solutions team is responsible for innovation, development and management of our products and services to address evolving risk and security needs for all of Mastercard’s customers across the world including Banks, Merchants, Fintechs and of course consumers. The Lead Data Scientist will be a key contributor in helping Mastercard develop and deliver actionable insights and products to help issuers, acquirers and merchants reduce fraud. What will you do? -You will be a key player in helping Mastercard extract value from existing data sources in order to better understand, detect and prevent fraud. -Use your data science expertise and skills to analyze worldwide fraud data to gain insights regarding fraud. -Apply modeling techniques to identify and understand fraud to protect the MasterCard payment network. -Build and manage new fraud related products and services that will provide value to our customers and increase revenue. All about you: <br

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Relocation support. Relocation assistance is stated. This does not establish visa sponsorship.
📍 Toronto, ON, Canada· Full-time
✓ Quality checkedCompany trend -100%

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . The Lead Industry Manager will manage the SMB Agency Sales Account Management business, responsible for revenue delivery and growth. They will lead a large vendor sales team in executing and operationalizing the strategy. What you’ll do: Drive retention and upsell across our 1K+ SMB agencies Retain and grow 7K+ managed advertisers Define the operational sales strategy by developing and standardizing operational systems to empower the SMB team to operate at scale Lead a high-performing team of sellers to deliver against quarterly revenue targets through effective planning, goal-setting, data analysis, and forecasting Manage relationship with Pinterest’s vendor partner Support team strategy for media planning, campaign management, media measurement and media channels (e-commerce, branding, formats and targeting) Motivate, m

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📍 Toronto, Quebec, Canada· Full-time
✓ High-confidence listingCompany trend -90.9%

From C$98.4K/yr

Quick readStrong listing-quality and freshness signals

We are looking for a Lead, Data Development, AI Platform to lead the team building and operating the technical platform behind Hootsuite's Analytics MCP. This includes routing infrastructure, orchestration services, agent infrastructure, and data pipelines that enable reliable AI-driven analysis at scale. You will set technical direction for the team, strengthen engineering practices, and translate target architecture and integration standards into secure, production-grade systems that Data Analytics & AI teams can confidently build on. This is a hands-on technical leadership role. You will stay close to the code while owning delivery outcomes, engineering quality, and the team's culture of craft and accountability. You will develop strong, well-reasoned recommendations on how the platform and orchestration architecture should evolve, seek approval at the Senior Manager and Director level, and then guide the team through disciplined execution. You will also partner closely with AI Context & Integration and AI Data Architecture to ensure the platform, context layer, semantic layer, and downstream agent workflows operate as one coherent system. WHAT YOU’LL DO: Lead the design and delivery of the orchestration layer that connects the Analytics MCP platform across its most complex surfaces, including query execution across schemas and models, federated data access between the data warehouse and external source systems, and multi-step agent workflows for cross-functional business processes. Develop clear technical recommendations for platform and orchestration architecture evolution, align those recommendations with Senior Manager and Director-level direction, and guide the team through disciplined execution within the approved architecture. Own the operational reliability, scalability, quality, and observability standards for core Analytics MCP components, including routing and agent infrastructure. Guide the team to build and operate these systems to prod

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📍 Toronto, Ontario, Canada· Full-time
✓ High-confidence listing

$175K – $225K/yr

Quick readStrong listing-quality and freshness signals

About Clutch Clutch is Canada's largest online used car retailer, delivering a seamless, hassle-free car-buying experience to drivers everywhere. Customers can browse hundreds of cars from the comfort of their home, get the right one delivered to their door, and enjoy peace of mind with our 10-Day Money-Back Guarantee. Named one of Canada's Top Growing Companies two years in a row and awarded a spot on LinkedIn's Top Canadian Startups list, we're looking to add curious, hard-working, and driven individuals to our growing team. Headquartered in Toronto, Clutch was founded in 2017. Clutch is backed by world-class investors including Canaan, BrandProject, Real Ventures, D1 Capital, and Upper90. To learn more, visit clutch.ca Technology Full TypeScript stack for front- and back-end, with some legacy JavaScript Front-end: ReactJS app with functional components and context API Back-end: ExpressJS with PostgreSQL database and Sequelize ORM Microservices architecture using Docker, Terraform, AWS ECS, and other AWS services Interservice communication via RabbitMQ and Apache Kafka About the role Clutch is seeking a Team Lead, Software Engineering to lead a team of engineers building and scaling our platform. This is a player-coach role: you'll split your time roughly evenly between hands-on engineering and team leadership, mentoring engineers, owning team delivery, and partnering with product to ship work that moves the business forward. You'll partner closely with other engineering leaders on technical direction and cross-team initiatives while owning the health, growth, and execution of your team. What you'll do Lead a team of 3–5 engineers, owning their growth, performance, career development, and day-to-day delivery Stay hands-on, contributing roughly half your time to code, architecture, and technical design across the stack Partner with Product, Design, and Data to translate business priorities into a clear roadmap and well-scoped engineering work Drive execution and de

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📍 Toronto, Canada· Full-time
✓ High-confidence listingCompany trend -74%

From C$102K/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. Data is at the heart of Lyft’s products and decision-making. You will leverage data and rigorous, analytical thinking to shape our products and make business decisions. This will involve performing rigorous product deep dives, identifying opportunities for product enhancements, and measuring the impact of product changes. The Airports team, within the Driver organization, focuses on the airport marketplace and the unique products designed for this use case. Airports are one of the most important, impactful, and complex parts of Lyft’s Rideshare business, as they are a key part of both the rider and driver Lyft experience and have unique dynamics. As an Analytics Lead on the Airport team, you will collaborate with our team of engineers, product managers, and designers to conduct thorough data deep dives on airport performance, challenge our current strategy, and recommend enhancements to facilitate market growth. The ideal candidate can apply strong business acumen to propose product and marketplace changes, and is comfortable working with a highly cross functional team. In this role, you will help us tackle problems such as: How should we determine pricing and earnings for airport rides? Who are our current airport drivers and what segment can we focus on to grow our supply? How does this strategy interact with driver bonuses? Which airports are underperforming and which key metrics can we use to identify and classify airport performance? What targets should we set for these key metrics and how do we efficiently monitor these metrics? What is driving high cancellation rates today and which types of riders/drivers are cancelling? What product changes can we implement to reduce cancellation rates? How are riders and drivers using different ride modes at airports, and how do we design

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