Enterprise Systems And Architecture Director in Canada

Why join us Brex is the intelligent finance platform that enables companies to spend smarter and move faster in more than 200 markets. By combining global corporate cards and banking with intuitive spend management, bill pay, and travel software, Brex enables founders and finance teams to accelerate operations, gain real-time visibility, and control spend effortlessly. Brex’s AI-native automation and world-class service eliminate manual expense and accounting tasks for customers so they can focus on what matters most. Tens of thousands of the world's best companies run on Brex, including DoorDash, Coinbase, Robinhood, Zoom, Plaid, Reddit, and SeatGeek. Working at Brex allows you to push your limits, challenge the status quo, and collaborate with some of the brightest minds in the industry. We’re committed to building a diverse team and inclusive culture and believe your potential should only be limited by how big you can dream. We make this a reality by empowering you with the tools, resources, and support you need to grow your career. Engineering at Brex Engineering at Brex is about building systems that scale with speed and intention. Our teams span Software, Data, Security, and IT, and operate with high autonomy and deep collaboration. We tackle hard technical problems, own our outcomes, and push for excellence at every level — from architecture to deployment. It’s an environment where engineering is a craft, and builders become leaders. What you’ll do As an engineer at Brex, you will help develop new products from concept to launch, whether for a 5-person startup or a 5,000-person-strong enterprise. We’re looking for folks with an interest in building products and tools, and who are comfortable in dealing with lots of moving pieces. You’ll be building customer-facing products that will drive direct business impact and shape our long-term technical vision with a high-quality bar. You'll have the opportunity to learn and push the frontier of providing the best fin

Why join us Brex is the intelligent finance platform that enables companies to spend smarter and move faster in more than 200 markets. By combining global corporate cards and banking with intuitive spend management, bill pay, and travel software, Brex enables founders and finance teams to accelerate operations, gain real-time visibility, and control spend effortlessly. Brex’s AI-native automation and world-class service eliminate manual expense and accounting tasks for customers so they can focus on what matters most. Tens of thousands of the world's best companies run on Brex, including DoorDash, Coinbase, Robinhood, Zoom, Plaid, Reddit, and SeatGeek. Working at Brex allows you to push your limits, challenge the status quo, and collaborate with some of the brightest minds in the industry. We’re committed to building a diverse team and inclusive culture and believe your potential should only be limited by how big you can dream. We make this a reality by empowering you with the tools, resources, and support you need to grow your career. Engineering at Brex Engineering at Brex is about building systems that scale with speed and intention. Our teams span Software, Data, Security, and IT, and operate with high autonomy and deep collaboration. We tackle hard technical problems, own our outcomes, and push for excellence at every level — from architecture to deployment. It’s an environment where engineering is a craft, and builders become leaders. What you’ll do As an engineer at Brex, you will help develop new products from concept to launch, whether for a 5-person startup or a 5,000-person-strong enterprise. We’re looking for folks with an interest in building products and tools, and who are comfortable in dealing with lots of moving pieces. You’ll be building customer-facing products that will drive direct business impact and shape our long-term technical vision with a high-quality bar. You'll have the opportunity to learn and push the frontier of providing the best fin

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! About the Role Are you passionate about secure-by-design software engineering? Do you want to be at the forefront of AI innovation and enterprise security? Cohere's North team is seeking a Software Engineer with a focus on security to join our mission and make a significant impact. This isn't a review-and-advise role, you'll own and ship production security features that customers rely on every day. Your Role: As a Senior Software Engineer with a security focus, you'll play a pivotal role in building and securing North's architecture. Your responsibilities will include: Software Development: Contributing to the core development of security features such as OIDC/OAuth flows and session management, ensuring North's AI agents are secure Secure Coding: Writing secure code to handle OIDC tokens, user claims, and sensitive data, adhering to best practices for JWT validation and encryption Authentication and Data Protection: Implementing authentication mechanisms including user login, token management, and authorization checks to maintain data integrity Tool Integration: Pulling in new tools to enhance North's security capabilities Dev

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! About Cohere and North Cohere is revolutionizing enterprise AI with North, an agentic AI platform designed to securely deploy AI agents and automations within organizations' infrastructure. North empowers employees to streamline workflows, automate repetitive tasks, and unlock actionable insights while ensuring data privacy and compliance. North combines cutting-edge generative and search models with customizable integrations to drive productivity and innovation at scale. Role Overview We are seeking an Agent Harness Product Manager to own the execution layer that makes North agents reliable, capable, and production-ready. This is a role that sits at the intersection of three domains: Agent Loop and Execution: Own the core agent runtime: tool orchestration, parallel execution, sub-agent delegation, sandbox code execution, and failure recovery. You will define how North agents plan and act across long, multi-step workflows and ensure the execution environment is robust enough for the most demanding enterprise tasks. You are expected to engage at the implementation level, contributing to architecture decisions alongside engineerin

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! About the Role Are you passionate about secure-by-design software engineering? Do you want to be at the forefront of AI innovation and enterprise security? Cohere's North team is seeking a Software Engineer with a focus on security to join our mission and make a significant impact. This isn't a review-and-advise role, you'll own and ship production security features that customers rely on every day. Your Role: As a Senior Software Engineer with a security focus, you'll play a pivotal role in building and securing North's architecture. Your responsibilities will include: Software Development: Contributing to the core development of security features such as OIDC/OAuth flows and session management, ensuring North's AI agents are secure Secure Coding: Writing secure code to handle OIDC tokens, user claims, and sensitive data, adhering to best practices for JWT validation and encryption Authentication and Data Protection: Implementing authentication mechanisms including user login, token management, and authorization checks to maintain data integrity Tool Integration: Pulling in new tools to enhance North's security capabilities Dev

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

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. The Lyft Business organization builds the platform that lets organizations move the people they depend on employees, clients, and customers. From the foundational mechanics of a company funding and provisioning a ride to the tailored workflows that get an employee to a client meeting or home after a late shift, we sweat the small stuff to make Lyft the transportation solution businesses build their programs on. As a Staff Software Engineer on the Lyft Business Team, you will act as a critical technical leader, taking holistic ownership of complex systems that span the rider experience, the administrator experience, and the enterprise integrations behind them — defining strategic roadmaps, driving cross-functional alignment, and driving engineering excellence to improve how organizations move their people. Responsibilities: Shape the long-term architecture for systems, taking accountability for both short-term functionality and long-term health Translate high-level business goals into actionable engineering projects. Own the technical roadmap from conception to delivery, managing cross-team dependencies and mitigating risks Champion improvements in system, observability, performance, and tech debt reduction, extending your influence beyond your immediate team Establish best practices for deployment, alerting, and on-call health. Take holistic ownership of the platform's stability, tracking down issues root causes and building preventive safeguards for your immediate scope and beyond. Drive alignment across product, design, and operations. Proactively resolve bottlenecks and make decisive trade-offs to protect system architecture from competing organizational priorities Mentor and level up the engineers around you. Delegate stretch opportunities, lead cross-team reviews, and foster a culture of s

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 Opportunity: Okta Access Gateway (OAG) Enterprises run on a mix of modern cloud services and mission-critical on-premises systems (such as Oracle E-Business Suite, SAP, PeopleSoft, and custom legacy web apps). Okta Access Gateway (OAG) solves the enterprise hybrid cloud challenge by extending Okta’s cloud identity, Adaptive MFA, and Zero Trust security policies to on-premises and legacy applications without requiring custom code changes or traditional VPNs. As the Engineering Manager for Okta Access Gateway in Toronto, you will lead and grow a team of software engineers building the next generation of our hybrid access and gateway infrastructure. You will partner closely with Product Management, Architecture, Security, and Quality teams to deliver high-throughput, mission-critical security software deployed across multi-cloud and enterprise datacenters globally. What You’ll Do People Leadership & Team Growth Lead, mentor, and empower an engineering team, fostering an inclusive, high-performance, and psychologically safe engineering culture. Drive career progression, goal setting, regular 1:1s, and continuous feedback to help engineers grow their technical and leadership skills. Attract, interview, and hire diverse engineering talent to scale Okta’s engineering presence in Toronto. Delivery & Operational Excellence Own the end-to-end execution and delivery of key product roadmap initiatives, balancing feature velocity, technical debt, and softwar

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 Okta Privileged Access Management (PAM) is an identity-centric approach to a common and critical privileged access use case. Our elegant Zero Trust architecture is purpose-built for the modern cloud and helps customers solve challenging security and operations pain points at scale. We're looking for a Senior level Platform Engineer to join a team of highly skilled and talented team players who are proud of what they own and deliver. Our elite team is fast, creative, and flexible; with a weekly release cycle and individual ownership, we expect great things from our engineers and reward them with stimulating new projects, new technologies, and the chance to have significant equity in a company that is changing the cloud computing landscape forever. What you’ll do Leverage cutting-edge AI pair-programmers and LLMs (such as Copilot and Claude) to accelerate the development of secure, enterprise-grade Privileged Access Management (PAM) products. Work with engineering teams to design, develop and deliver cloud-based infrastructure projects on a modern tech stack (Kubernetes/EKS, RDS, DynamoDB, Kinesis, MKS, Redis, OpenSearch, Docker, Terraform on AWS) Drive evaluation, development, and rollout of microservices Operate, support, and upgrade shared services and frameworks. Scale these as their usage invariably grows along with Okta's business. Evaluate and scale existing systems to meet specialized requirements and support Okta’s future business ne

Solution Architect Sigma Computing The SA role has evolved. Here’s the version we’re hiring for. The SA job in 2026 is not the SA job in 2023. Three things now sit at the center of how we evaluate this role. This hire has to do all three at a senior level, with the architectural depth to back it up. 1. Use AI every day to do the job better. If you are not using Claude, ChatGPT, Cursor, or equivalents to accelerate your account prep, architecture diagramming, prototype builds, RFP responses, and discovery synthesis, you are getting outworked by SAs who are. We expect this hire to treat AI tooling as default infrastructure, not novelty. Come with a point of view on what you run, why, and how you use it to compress weeks of work into days. 2. Sell AI into the account. Buyers want to talk about agents, MCP, A2A, context engineering, and which model is powering what. You have to be fluent. You know Sigma’s AI surface cold: Sigma Assistant in build, analyze, and plan modes, AI functions, input tables with LLM enrichment, MCP integration, and warehouse-native agent patterns. You can architect Sigma agents and warehouse agents into a customer’s stack and explain the tradeoffs to a head of data and a CISO in the same call. You also speak credibly about Claude, OpenAI, Gemini, and the broader stack the customer already runs. 3. Sell against AI. Every enterprise deal has AI competition in it. Sometimes it is Databricks Genie. Sometimes it is Snowflake Cortex Analyst. Sometimes it is a systems integrator pitching a bespoke agent built over the weekend. You know where each of these breaks at scale, where Sigma’s warehouse-native architecture wins on governance, freshness, and cost, and how to draw the line for a skeptical CDO without hand-waving. You can defend that position in an architecture review, on a security questionnaire, and across three follow-up calls. About Sigma Sigma is the AI runtime environment for the modern enterprise. Teams build apps, agents, an

Who we are About Stripe Stripe, LLC. 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. What you’ll do Responsibilities Partner with the Tax team stakeholders to design and implement features of our financial systems that include Oracle Cloud Applications (Financials, TRCS, Fusion Tax), Stripe homegrown Tax Solutions and many other tools. Identify opportunities to automate Tax processes, work on transformation initiatives, implement SOX controls and maintain our financial Applications. Lead Finance systems (primarily Tax area including but not limited to Direct and Indirect Taxes) projects and strategic initiatives - including implementation of new tools and business process changes - from requirements, tool selection, system design, implementation, UAT, training, go-live & post go-live support. Serve as a technology liaison with Tax stakeholders to understand their pain points, opportunities for process improvements, automation & efficiency gains, create strategic roadmap and provide them with technology solutions. Demonstrate an understanding of increasingly complex sales tax, transfer pricing and Tax provisioning concepts and effectively apply knowledge to develop and maintain tax systems and data flows. Design solutions and make architecture decisions by benchmarking with industry best practices to help us scale for the future. Partner with Engineering product teams to develop & deliver technical solutions to optimize financial workflow and integration with other Stripe internal sy

About Scale Scale’s mission is to develop reliable AI systems for the world’s most important decisions. As the leading AI data foundry, we provide the high-quality data and full-stack technologies that power the world’s most advanced models — fueling breakthroughs in generative AI, defense, and autonomous vehicles. We partner with leading enterprises and governments to bring AI into production that performs when it matters most, combining rigorous evaluation with full-stack deployment so our customers can build AI they can trust. About the Team Applied Intelligence Systems (AIS) is part of the Scale Generative AI Platform (SGP), focused on pushing the frontier of what agentic applications can do across diverse enterprise and government use cases. We build the infrastructure and tooling that power agentic AI in production, paired with applied ML research, design, and evaluation to ensure these systems perform reliably at the scale our customers demand. AIS spans multiple workstreams — agent evaluation and oversight, orchestration and tool-use infrastructure, model and systems optimization, and applied research on new agent capabilities — and this role is not scoped to any single one of them. We’re growing fast, with increasing traction across both commercial and public sector customers, and we’re just getting started — this team will define what dependable, production-grade agentic AI looks like. About the Role As a Staff Machine Learning Research Engineer, you will operate across the full breadth of AIS’s technical needs — wherever the hardest ML problem in agentic AI happens to be that quarter. This could mean training and fine-tuning models, designing evaluation and observability systems, building improvement loops from production data, prototyping novel agent architectures, or designing internal systems and tooling that boost productivity across teams. You’re not tied to one team’s roadmap; you’re expected to move to where the technical leverage is highest, and t

At Scale, our mission is to develop reliable AI systems for the world's most important decisions. Our products provide the high-quality data and full-stack technologies that power the world's leading models, and help enterprises and governments build, deploy, and oversee AI applications that deliver real impact. Scale Frontier Data is the organization behind the training and evaluation data that frontier labs depend on. We build the systems, tooling, and expert workflows that turn hard human expertise into signals that models can learn from, across reasoning, coding, agentic tool use, and domain expertise. About our Customer Platform team: Our Customer Platform Team plays a pivotal role in integrating our platform with external systems and ensuring seamless, reliable connectivity for both internal users and customers. As the leader of this team, you’ll drive the strategy, architecture, and development of our connectivity solutions, focusing on API integration, distributed systems, and a robust data platform. Your role will be crucial in maintaining and enhancing our platform’s ability to meet the needs of both our internal and external stakeholders. Responsibilities: Own large areas within our product Comfortable working cross functionally, whether that be internal or external customers Build features end-to-end: front-end, back-end, system design, debugging and testing Deliver experiments at a high velocity and level of quality to engage our customers Work across the entire product lifecycle from conceptualization through production Influence the culture, values, and processes of a growing engineering team Inspire and mentor less experienced engineers Collaborating with cross-functional teams to define, design, and ship new product features and experiences. Requirements: At least 7-10 years of relevant experience is preferred Track record of shipping high-quality products and features at scale Desire to work in a very fast-paced environment Abil

About Scale AI Scale AI is the data foundation for AI, helping organizations build and deploy reliable production AI applications. We partner with the world's leading enterprises and government organizations to accelerate their AI transformation through frontier AI systems that solve real business problems. Every day, we work with organizations across finance, healthcare, manufacturing, media and telecommunications to build production AI agents that automate complex workflows, help humans, reason over enterprise knowledge, and operate safely at scale. The Opportunity Applied AI is moving faster than ever. New foundation models, reasoning techniques, agent architectures, and research papers emerge every week. Yet building AI systems that reliably solve real-world problems remains one of the hardest engineering challenges. As a Frontier Agent Engineer (Applied AI) , you'll bridge the gap between cutting-edge AI research and production deployment. You'll work directly with enterprise customers to design, evaluate, and deploy intelligent systems that combine frontier models with structured knowledge, retrieval, traditional machine learning, and enterprise software. Unlike traditional ML roles that focus on a single model or product, you'll work across a diverse portfolio of AI challenges spanning multiple industries and use cases. You may build a multi-agent research system and then participate in designing a customer intelligence platform, a healthcare copilot, or an autonomous workflow for a Fortune 100 company. If you enjoy reading new AI papers, experimenting with the latest models, and shipping production systems that create measurable business impact, you'll fit right in. What You'll Build Frontier AI Systems Design and deploy production AI agents that leverage the latest advances in large language models, reasoning, retrieval, memory, and tool use. Architect intelligent systems that combine LLMs, traditional machine learning, structured knowledge, enterprise data

About Scale AI Scale AI is the data foundation for AI, helping organizations build and deploy reliable production AI applications. We partner with the world's leading enterprises and government organizations to accelerate their AI transformation through frontier AI systems that solve real business problems. Every day, we work with organizations across finance, healthcare, manufacturing, media and telecommunications to build production AI agents that automate complex workflows, help humans, reason over enterprise knowledge, and operate safely at scale. The Opportunity Applied AI is moving faster than ever. New foundation models, reasoning techniques, agent architectures, and research papers emerge every week. Yet building AI systems that reliably solve real-world problems remains one of the hardest engineering challenges. As a Senior Frontier Agent Engineer (Applied AI) , you'll bridge the gap between cutting-edge AI research and production deployment. You'll work directly with enterprise customers to design, evaluate, and deploy intelligent systems that combine frontier models with structured knowledge, retrieval, traditional machine learning, and enterprise software. Unlike traditional ML roles that focus on a single model or product, you'll work across a diverse portfolio of AI challenges spanning multiple industries and use cases. You may build a multi-agent research system and then participate in designing a customer intelligence platform, a healthcare copilot, or an autonomous workflow for a Fortune 100 company. If you enjoy reading new AI papers, experimenting with the latest models, and shipping production systems that create measurable business impact, you'll fit right in. What You'll Build Frontier AI Systems Design and deploy production AI agents that leverage the latest advances in large language models, reasoning, retrieval, memory, and tool use. Architect intelligent systems that combine LLMs, traditional machine learning, structured knowledge, enterpri