Ai Senior Systems Engineer in Canada

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

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

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

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

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

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

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

About the Team OpenAI’s User Operations team shepherds our customer’s 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 are looking for a leader to build and scale our Support Engineering team, which will collaborate directly with our strategic enterprise accounts, our product and engineering teams, as well as our field teams to solve some of the most difficult technical problems faced by our customers. You will lead one of the best technical troubleshooting teams at OpenAI, and our customers and Engineering teams will look to you for technical guidance in addressing the most technically difficult issues in our environment. You will play an integral role in building knowledge within the team and be part of strategic initiatives for organizational and process improvements. Working directly with our most strategic customers - You will be crucial to the success of the most innovative, disruptive, and high-scale AI solutions being built with the OpenAI platform. This team will handle high difficulty situations and issues. The team will be global, providing 24x7 technical coverage for our customers. This will be an opportunity to build this new team from first principles - your leadership will determine the future of this organization. The ideal candidate will have a combination of technical capabilities mixed with strong leadership and systems building strength. This Toronto-based role is currently remote and is expected to transition to a