System Engineer in Canada

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 Revenue and Financial Automation (RFA) team at Stripe is building a modern, revenue-focused, financial management platform for fast-growing, digital-native companies. 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 Usage-Based Billing, and providing recovery and retention tools to prevent customer churn. What you'll do As an engineer on the team, you'll be responsible for shaping and building a suite of products that let our users model and operate their business more efficiently. You'll work on projects that span technologies, systems, and processes where you'll design, build, test, and ship code every day. In this cross-functional role, you'll collaborate with experts in infrastructure, security, design, and operations to build business-critical internal and external features that power Stripe users around the world. Responsibilities Design the next generation of Stripe products to meet the high-growth needs of our company and customers for years to come Deliver value through a strong collaborative, user-first approach with stakeholders and customers Mentor engineers to help them grow Debug and solve critical production issues across services and multiple levels of the stack Who you are We're looking for someone who meets the

About the Team OpenAI’s User Operations team shepherds our customers’ adoption of AI and ensures that our customers' product experience is nothing short of exceptional. We are building the very first post-AGI support team. We resolve complex issues, provide technical guidance, and support customers in maximizing value and adoption from deploying our products. We work closely with Sales, Technical Success, Product, Engineering and others, to deliver the best possible experience to our customers at scale. OpenAI's customers represent a range of diverse backgrounds and maturity, from early-stage startups to established global enterprises. About the Role We’re looking for dedicated, experienced, and deeply curious individuals to help solve some of the most complex challenges faced by our customers while building the future of post-AGI support alongside us. In this role, you’ll work directly with customers through support tickets and live calls, troubleshooting high-impact issues and resolving novel, often ambiguous technical problems in one of the fastest-moving environments in technology. As AI adoption rapidly accelerates, the work you do will directly support mission-critical systems being built on OpenAI’s platform, serving as a critical line of defense for customers operating at massive scale. Beyond resolving technical issues, you’ll help define what world-class support looks like in an AGI-driven future. You’ll partner closely with Engineering, Product, and Operations to improve systems, reduce bugs, and elevate the customer experience, while leveraging automation, agents, and our own AI technology to transform how support operates at scale. This Toronto-based role is currently remote and is expected to transition to an in-office arrangement. In this role, you will: Work directly with customers to troubleshoot and resolve their most complex technical issues, including API failures, integration challenges, authentication errors, and production incidents. Providing

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. About the Role We're building out the Customer Success Engineering team at Postman, and we need business-minded engineers who can solve real problems at scale. You will partner closely with Customer Success Managers and own the “How” of technical solutioning. This is a consultative role that requires both depth and versatility. This is no support role; you'll be the technical architect of Customer Success, turning complex and nuanced challenges into repeatable solutions that benefit our entire enterprise customer base. As a CSE, you consult on the technical implementation path. When a customer needs to get from point A to point B, you figure out how to make it happen - whether that means architecting workflows within Postman, guiding integrations, or creating pragmatic workarounds when the product doesn't quite fit. A key part of this role is turning individual solutions into reusable assets that shorten time to value for future customers. We don’t believe in reinventing the wheel each time. Success in this role requires a blend of technical expertise, systems thinking, and the ability to translate complex business objectives into

About Glean: Glean is the Work AI platform that helps everyone work smarter with AI. What began as the industry’s most advanced enterprise search has evolved into a full-scale Work AI ecosystem, powering intelligent Search, an AI Assistant, and scalable AI agents on one secure, open platform. With over 100 enterprise SaaS connectors, flexible LLM choice, and robust APIs, Glean gives organizations the infrastructure to govern, scale, and customize AI across their entire business - without vendor lock-in or costly implementation cycles. At its core, Glean is redefining how enterprises find, use, and act on knowledge. Its Enterprise Graph and Personal Knowledge Graph map the relationships between people, content, and activity, delivering deeply personalized, context-aware responses for every employee. This foundation powers Glean’s agentic capabilities - AI agents that automate real work across teams by accessing the industry’s broadest range of data: enterprise and world, structured and unstructured, historical and real-time. The result: measurable business impact through faster onboarding, hours of productivity gained each week, and smarter, safer decisions at every level. Recognized by Fast Company as one of the World’s Most Innovative Companies (Top 10, 2025), by CNBC’s Disruptor 50, Bloomberg’s AI Startups to Watch (2026), Forbes AI 50, and Gartner’s Tech Innovators in Agentic AI, Glean continues to accelerate its global impact. With customers across 50+ industries and 1,000+ employees in more than 25 countries, we’re helping the world’s largest organizations make every employee AI-fluent, and turning the superintelligent enterprise from concept into reality. If you’re excited to shape how the world works, you’ll help build systems used daily across Microsoft Teams, Zoom, ServiceNow, Zendesk, GitHub, and many more - deeply embedded where people get things done. You’ll ship agentic capabilities on an open, extensible stack, with the craf

About Glean: Glean is the Work AI platform that helps everyone work smarter with AI. What began as the industry’s most advanced enterprise search has evolved into a full-scale Work AI ecosystem, powering intelligent Search, an AI Assistant, and scalable AI agents on one secure, open platform. With over 100 enterprise SaaS connectors, flexible LLM choice, and robust APIs, Glean gives organizations the infrastructure to govern, scale, and customize AI across their entire business - without vendor lock-in or costly implementation cycles. At its core, Glean is redefining how enterprises find, use, and act on knowledge. Its Enterprise Graph and Personal Knowledge Graph map the relationships between people, content, and activity, delivering deeply personalized, context-aware responses for every employee. This foundation powers Glean’s agentic capabilities - AI agents that automate real work across teams by accessing the industry’s broadest range of data: enterprise and world, structured and unstructured, historical and real-time. The result: measurable business impact through faster onboarding, hours of productivity gained each week, and smarter, safer decisions at every level. Recognized by Fast Company as one of the World’s Most Innovative Companies (Top 10, 2025), by CNBC’s Disruptor 50, Bloomberg’s AI Startups to Watch (2026), Forbes AI 50, and Gartner’s Tech Innovators in Agentic AI, Glean continues to accelerate its global impact. With customers across 50+ industries and 1,000+ employees in more than 25 countries, we’re helping the world’s largest organizations make every employee AI-fluent, and turning the superintelligent enterprise from concept into reality. If you’re excited to shape how the world works, you’ll help build systems used daily across Microsoft Teams, Zoom, ServiceNow, Zendesk, GitHub, and many more - deeply embedded where people get things done. You’ll ship agentic capabilities on an open, extensible stack, with the craf

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 Red Team team’s mission is to proactively identify and simulate real-world threats against Robinhood’s platforms, properties, and people. Through red teaming and adversarial simulations, the team evaluates security controls, uncovers vulnerabilities, and helps continuously strengthen Robinhood’s overall security posture in close partnership with Detection & Response, Physical Security, and Engineering. As a Staff Offensive Security Engineer, you will take a hands-on role in designing and executing stealthy adversarial simulations to validate assumptions and uncover gaps in detection and response. You’ll leverage threat modeling, penetration testing, and research-driven techniques to emulate sophisticated attackers, while collaborating cross-functionally to improve defenses and shape more secure systems. This role is based in our Toronto, Canada office(s), 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-performing teams. What you’ll

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. Robinhood's Enterprise Security team is at the forefront of AI security, designing safety guardrails for cutting-edge AI and driving modern enterprise-wide security tooling standards. As a Senior Corporate Security Engineer on our Corporate Systems team, you will operate at the center of our enterprise security infrastructure, maintaining the control plane for user-facing security tooling and building innovative solutions that keep our employees and platform secure! In this role, you will combine security engineering, systems administration, and hands-on AI agent development to drive key automation and safety initiatives. Joining a lean, high-impact team, you will have high visibility and direct empowerment to take strategic initiative, solve complex technical challenges, and shape Robinhood's AI security posture. This role is based in our Menlo Park or Bellevue office(s), 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-performing teams.

Overview We are seeking a hands-on Director of AI Software Engineering to lead and scale AI engineering efforts supporting multiple business units across Governance, Risk, and Compliance (GRC). This role sits at the intersection of product delivery, platform evolution, and applied AI—driving real-world impact across core workflows. This is not a pure management role. We are looking for a builder who leads from the front, someone who has recently written production code, shipped systems end-to-end, and can operate comfortably in ambiguity while aligning teams and stakeholders. What You’ll Do Lead AI Engineering Across GRC Own delivery of AI-powered capabilities embedded directly into business unit workflows (e.g., risk analysis, compliance automation, reporting, due diligence) Partner with product, data, and platform teams to translate business problems into scalable AI systems Stay Hands-On Contribute to architecture, code reviews, and critical path implementation Prototype and validate new approaches (LLMs, agents, retrieval systems, classification pipelines, etc.) Set engineering standards for performance, reliability, and cost efficiency Build and Scale Teams Lead and mentor a high-performing team of AI/ML and software engineers Drive hiring, coaching, and career development Establish a culture of ownership, speed, and technical excellence Drive Execution Deliver production-grade systems—not experiments Balance speed with rigor (security, privacy, compliance) Operate across multiple concurrent initiatives with clear prioritization Communicate and Influence Act as a bridge between engineering and business stakeholders Clearly articulate trade-offs, risks, and outcomes to senior leadership Align cross-functional teams around shared goals and timelines What We’re Looking For Proven Builder 10+ years in software engineering, with recent hands-on coding experience Demonstrated track record of shipping production systems at scale Experience with modern

About Dialpad Dialpad is the AI platform for customer experience, built to resolve customer problems in real time across voice and digital. Our AI agents learn from your best human agents and improve with every interaction, helping organizations understand their customers, deliver better experiences, increase operational efficiencies, and build a lasting competitive advantage. Unlike legacy systems built to route and answer, or standalone agentic bot vendors built to deflect, Dialpad was built to resolve. Our AI agents and human agents operate on a single platform with shared context, allowing Agentic AI to resolve issues, advance deals, and eliminate busywork through automation while seamlessly handing conversations to humans when needed, with full context preserved. Market-leading brands, including Randstad, Motorola Solutions, Netflix, the San Diego Padres, the Colorado Rockies Baseball Club, and Cal Athletics, trust Dialpad. Dialpad is backed by Andreessen Horowitz, GV, ICONIQ Capital, and T-Mobile. Being a Dialer At Dialpad, AI isn’t just a feature; it’s how our teams do their best work every day. We put powerful AI tools in every employee’s hands so they can move faster, think bigger, and achieve more. We believe every conversation matters. And we’ve built the platform that turns those conversations into insight and action, for our customers and ourselves. We look for people who are intensely curious and hold themselves to a high bar. Our ambition is significant, and achieving it requires a team that operates at the highest level. We seek individuals who embody our core traits: Scrappy, Curious, Optimistic, Persistent, and Empathetic . Your role As a Sr. SDET in Agentic QA, you will own the test automation and quality frameworks that support Dialpad’s AI Voice Agent services. You will develop automated tests for end-to-end product experiences, from frontend UI to backend services to APIs to audio/text interactions. You will test orchestration flows, agent conf

About Dialpad Dialpad is the AI platform for customer experience, built to resolve customer problems in real time across voice and digital. Our AI agents learn from your best human agents and improve with every interaction, helping organizations understand their customers, deliver better experiences, increase operational efficiencies, and build a lasting competitive advantage. Unlike legacy systems built to route and answer, or standalone agentic bot vendors built to deflect, Dialpad was built to resolve. Our AI agents and human agents operate on a single platform with shared context, allowing Agentic AI to resolve issues, advance deals, and eliminate busywork through automation while seamlessly handing conversations to humans when needed, with full context preserved. Market-leading brands, including Randstad, Motorola Solutions, Netflix, the San Diego Padres, the Colorado Rockies Baseball Club, and Cal Athletics, trust Dialpad. Dialpad is backed by Andreessen Horowitz, GV, ICONIQ Capital, and T-Mobile. Being a Dialer At Dialpad, AI isn’t just a feature; it’s how our teams do their best work every day. We put powerful AI tools in every employee’s hands so they can move faster, think bigger, and achieve more. We believe every conversation matters. And we’ve built the platform that turns those conversations into insight and action, for our customers and ourselves. We look for people who are intensely curious and hold themselves to a high bar. Our ambition is significant, and achieving it requires a team that operates at the highest level. We seek individuals who embody our core traits: Scrappy, Curious, Optimistic, Persistent, and Empathetic . Your role As a Software Engineer, you’ll be responsible for developing and maintaining features to enhance customers’ day-to-day communication experience. You’ll work closely with customers and customer-facing teams to provide industry-leading calling workflows. On this team, you’ll be participating in an effort to combine tradi

Who are we? Cohere is the leading security-first enterprise AI company. We build cutting-edge foundation AI models and end-to-end products that are designed to solve real-world business problems. We’re training and deploying frontier models for enterprises who are building AI systems. We believe that our work is instrumental to the widespread adoption of AI and we are looking for folks that want to be part of that. We obsess over what we build. Each one of us is responsible for contributing to increasing the capabilities of our models and the value they drive for our customers. Cohere is a team of researchers, engineers, designers, and more, who are all passionate about their craft. We are a global technology company headquartered in Toronto with key offices in London, New York City, San Francisco, Montreal, Paris, Berlin and Seoul. Join us! Why this role? This role will focus on breaking down engineering tasks such as reporting, component search and handling of material billing/information into individual steps that can be tackled through tool use. Your breakdown will teach the Cohere model the logic needed to complete each task. Please Note: This is a part-time independent contractor position available within Canada . We seek candidates who are able to commit to 16 hours per week minimum at a 30 CAD/hour contract rate. This role is BYOD 💻 - Bring Your Own Device (laptop). Remote work within Canada. 12 month contract. Performance incentives included! As a Data Annotation Specialist, you will: Evaluate the model's ability to respond to engineering procedures and workflows Task models to complete engineering tasks along with verified information to evaluate the accuracy of the model's responses Label, proofread, and improve machine-written and human-written engineering-related outputs. Follow our style guide, and make recommendations on unique situations that fall outside of its scope. You may be a good fit if you have: 3+ years of industry experience working in eng

Who are we? Cohere is the leading security-first enterprise AI company. We build cutting-edge foundation AI models and end-to-end products that are designed to solve real-world business problems. We’re training and deploying frontier models for enterprises who are building AI systems. We believe that our work is instrumental to the widespread adoption of AI and we are looking for folks that want to be part of that. We obsess over what we build. Each one of us is responsible for contributing to increasing the capabilities of our models and the value they drive for our customers. Cohere is a team of researchers, engineers, designers, and more, who are all passionate about their craft. We are a global technology company headquartered in Toronto with key offices in London, New York City, San Francisco, Montreal, Paris, Berlin and Seoul. Join us! Why this role? This role will focus on evaluating coding tasks, requiring you to review and debug code, navigate repository architecture, and analyze model trajectories. Your work will contribute to our model development efforts and the logic our models apply when completing task requests. Please note : This is a part-time independent contractor position available within Canada. We seek candidates who are able to commit to 16 hours per week minimum at a 40 CAD/hour contract rate. This role is BYOD 💻 - Bring Your Own Device (laptop). Remote work within Canada. 12 month contract. Performance incentives included! As a Data Annotation Specialist, you will: Evaluate the model's ability to respond to coding requests, workflows, and code base-related questions using available tools. Assess agent trajectories and model capabilities for code generation and debugging requests. Prompt models to complete complex coding tasks and review the accuracy of generated responses. Label, proofread, and improve machine-written and human-written software engineering-related outputs. Report quality and performance trends related to model/agent behavio

About Us Twitch is the world’s biggest live streaming service, with global communities built around gaming, entertainment, music, sports, cooking, and more. It is where thousands of communities come together for whatever, every day. We’re about community, inside and out. You’ll find coworkers who are eager to team up, collaborate, and smash (or elegantly solve) problems together. We’re on a quest to empower live communities, so if this sounds good to you, see what we’re up to on LinkedIn and X , and discover the projects we’re solving on our Blog . Be sure to explore our Interviewing Guide to learn how to ace our interview process. About the Role Platform Core Engineering (PCE) builds the foundational systems, frameworks, and tooling that Twitch's engineers build on every day. As a Senior Product Manager on PCE, your customers are developers, and your success depends on earning their trust. You will own a platform product area and be measured on whether developers actually adopt, rely on, and advocate for what you ship. This is a deeply technical, senior individual-contributor role. You are expected to be hands-on with modern AI development tools, to understand the technology you are shaping at a real level (not just at the surface), and to hold credibility in a room full of engineers. You can be based out of one of the Twitch offices including San Francisco, Seattle, Los Angeles, Irvine, or New York City. You Will: Own the strategy and roadmap for a PCE platform area, balancing near-term developer needs with a 1 to 2 year technical vision. Treat developers as your customers: understand their workflows, earn their trust, and prioritize the capabilities that make them faster and more effective. Work directly with Senior Engineering Managers and Principal Engineers to define technical and organizational needs and build a cohesive platform ecosystem. Define and drive the platform metrics that matter. Drive alignment across dependent

About Us Twitch is the world’s biggest live streaming service, with global communities built around gaming, entertainment, music, sports, cooking, and more. It is where thousands of communities come together for whatever, every day. We’re about community, inside and out. You’ll find coworkers who are eager to team up, collaborate, and smash (or elegantly solve) problems together. We’re on a quest to empower live communities, so if this sounds good to you, see what we’re up to on LinkedIn and X , and discover the projects we’re solving on our Blog . Be sure to explore our Interviewing Guide to learn how to ace our interview process. About the Role Platform Core Engineering (PCE) builds the foundational systems, frameworks, and tooling that Twitch's engineers build on every day. As a Senior Product Manager on PCE, your customers are developers, and your success depends on earning their trust. You will own a platform product area and be measured on whether developers actually adopt, rely on, and advocate for what you ship. This is a deeply technical, senior individual-contributor role. You are expected to be hands-on with modern AI development tools, to understand the technology you are shaping at a real level (not just at the surface), and to hold credibility in a room full of engineers. You can be based out of one of the Twitch offices including San Francisco, Seattle, Los Angeles, Irvine, or New York City. You Will: Own the strategy and roadmap for a PCE platform area, balancing near-term developer needs with a 1 to 2 year technical vision. Treat developers as your customers: understand their workflows, earn their trust, and prioritize the capabilities that make them faster and more effective. Work directly with Senior Engineering Managers and Principal Engineers to define technical and organizational needs and build a cohesive platform ecosystem. Define and drive the platform metrics that matter. Drive alignment across dependent

About Dialpad Dialpad is the AI platform for customer experience, built to resolve customer problems in real time across voice and digital. Our AI agents learn from your best human agents and improve with every interaction, helping organizations understand their customers, deliver better experiences, increase operational efficiencies, and build a lasting competitive advantage. Unlike legacy systems built to route and answer, or standalone agentic bot vendors built to deflect, Dialpad was built to resolve. Our AI agents and human agents operate on a single platform with shared context, allowing Agentic AI to resolve issues, advance deals, and eliminate busywork through automation while seamlessly handing conversations to humans when needed, with full context preserved. Market-leading brands, including Randstad, Motorola Solutions, Netflix, the San Diego Padres, the Colorado Rockies Baseball Club, and Cal Athletics, trust Dialpad. Dialpad is backed by Andreessen Horowitz, GV, ICONIQ Capital, and T-Mobile. Being a Dialer At Dialpad, AI isn’t just a feature; it’s how our teams do their best work every day. We put powerful AI tools in every employee’s hands so they can move faster, think bigger, and achieve more. We believe every conversation matters. And we’ve built the platform that turns those conversations into insight and action, for our customers and ourselves. We look for people who are intensely curious and hold themselves to a high bar. Our ambition is significant, and achieving it requires a team that operates at the highest level. We seek individuals who embody our core traits: Scrappy, Curious, Optimistic, Persistent, and Empathetic . Your role Dialpad is looking for a Senior Engineering Manager to lead the team at the very core of the Dialpad experience: calling. Reporting directly to the VP of Engineering, you'll own the calling experience end-to-end: frontend, backend, and hardware devices (first-class desk phones, Room Phones, ATAs, and DECT solutions). Y