AI Support Engineer - Toronto

About the Team The Technical Support team is responsible for ensuring that developers and enterprises can reliably build mission critical solutions using OpenAI models. We provide technical guidance, resolve complex issues and support customers in maximizing value and adoption from deploying our highly-capable models. We work closely with Technical Success, Product, Engineering and others to deliver the best possible experience to our customers at scale. We think from an automation-first mindset and leverage the latest in AI to scale our support operations. Join the Senior Support Engineering (SSE) team at OpenAI and help shape the future of Technical Support in the age of AI. About the Role We are looking for a Senior Support Engineer to collaborate directly with our strategic enterprise accounts and product teams, helping solve some of the most difficult problems faced by our Customers. You will be part of the best technical troubleshooting team 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. As a Senior Support Engineer, you will design and run operational processes to monitor our top strategic customers and a 24x7 response team. You’ll work closely with our Infrastructure and Engineering teams to deliver the best possible experience to customers at scale. 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 API platform. The nature of this role will be low volume, high difficulty. This Toronto-based role is currently remote and is expected to transition to an in-office arrangement. In this role, you will: Be among the foremost technical and troubleshooting experts for our API platform at OpenAI. You are the last line of defense before the core Engineering team. Proactively identify and implement opportunities to scale suppor

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 You are a deep technical architect. Whether it's a Fortune 500 CTO or a startup founder, you know how to read the room and steer it. You have handled enough OAuth token flows, SCIM failures, and multi-product integration edge cases to spot root issues fast. In this role, you will help shape how developers understand identity at scale. You serve as the top technical escalation point for our support team. You are our domain expert. You influence product roadmaps. You mentor engineers. You challenge standard practices. You raise the bar across the entire global team. You handle ambiguity well. You operate with full autonomy. You focus on delivering outcomes that unblock our most complex accounts. What You Do Strategic Escalations and Architecture This is not primarily a queue role. You will mostly engage on cases that exceed senior engineer scope, the ones that need architecture judgment, not triage. End-to-End Ownership: Resolve our most complex developer cases, including multi-product architectures, ISV integration designs, and strategic account escalations. Cross-Functional Bridge: Serve as the technical link between Developer Support and ISV Partnerships, working directly with strategic partners on integration design. Architectural Consulting: Join customer and partner calls to advise on architecture and resolve issues beyond standard support scope. Product and Executive Engagement Roadmap Influence: Partner with Product Management and Engineering

About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the Role At Sentry, Support is an engineering discipline. Our customers are the greatest technical minds in the world—developers at elite enterprises building the future of software—and they deserve answers that go deeper than a knowledge base link. We are architecting the Technical Support engine . We’re looking for a veteran engineer to help us redefine the standard of technical support by combining deep human expertise with autonomous agentic systems. You are a debugger of both code and systems. You will treat support volume as a data signal to build automated resolution paths, ensuring our human engineers only touch the most complex, high-impact architectural puzzles. Sentry Support Engineers aren't just clearing queues; they are Orchestrators . You will engage with our users across GitHub, Discord, and our internal systems, while acting as the Technical Lead for our Agentic Ops. You ensure that when a developer asks a complex question, our systems have the right context and a seamless "Human-in-the-Loop" path to you when deep, nuanced expertise is required. In this role you will Master the Sentry Ecosystem & Support Elite Developers Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments. Support the Great Minds: Act as a strategic consultant for senior engineers at our largest enterprise customers, solving high-stakes architectural challenges that push the boundaries of observability. Troubleshoot SDK Implementations: Go deep into the source code of Sentry’s SDKs to help developers instrument complex frameworks and custom environments. Engin

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 Safety and Customer Care (SCC) team at Lyft manages over 1.7 million monthly human and AI interactions and serves as Lyft's primary direct touchpoint with riders and drivers. We handle critical infrastructure that powers both human associates and AI agents to make riders and drivers feel safe and comfortable while riding or driving with Lyft, transforming every support interaction into a moment of genuine connection. Agentic AI is at the center of how we scale that mission. We fine-tune and align open-source models, build AI-powered support agents, and develop end-to-end AI agents for safety case management, systems that reason over complex, high-stakes cases and drive them to resolution. SCC brings together ML, data, backend, and product engineers alongside data scientists and operations partners to transform these systems. As a Machine Learning Engineer on the SCC team, you will fine-tune and align models and build AI Agents that power how riders and drivers get help. Your work spans the full loop: post-training open-source models for our domain, composing them into multi-step agents, and building the evaluation that proves they are safe to ship in a customer-facing, safety-critical setting. Post-train and adapt open-source LLMs for SCC use cases using SFT, LoRA, and preference-tuning methods (RLHF, RLAIF, RLVR). Design and build AI-powered support agents and end-to-end agents for safety case management using LangGraph or equivalent agentic frameworks. Own the evaluation data flywheel, offline and online, that defines what "good" looks like and build benchmarks for the team to hill-climb. Turn interaction feedback into training data and learning signals, closing the data flywheel that continuously improves the models. Responsibilities: Conduct literature review and build post-training fra

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. We're looking for a Workato/Boomi Integration Engineer to build and support enterprise automation, with a focus on Legal systems integration (CLM, e-signature, matter management, compliance). You'll work across iPaaS, APIs, and AI/agentic tooling (Workato Genie, AI Skills, MCP servers) to connect Legal and other business systems. Responsibilities: Design and build Recipes and process automations across multiple systems, including AI-powered workflows using Workato Genie and MCP servers. Build and support AI Agents (Genies) for Legal and business-process automation, including prompt design and IDP for unstructured Legal content (contracts, filings). Design and manage secure API endpoints (REST/SOAP) and SFTP connections; build ETL/data-sync pipelines across formats (JSON, XML, CSV, EDI). Deploy and manage On-Premises Agents (OPA) for secure, behind-firewall connectivity. Maintain platform environments and security (RBAC, SSO, versioning); monitor jobs and troubleshoot failures. Build employee-facing tools (Workbot/ChatOps, Workflow/AgentX Apps, Slack integrations) with human-in-the-loop steps. Integrate business applications (CRM, HR, Finance, LMS, Legal, Budget & Forecast) via Boomi, with emphasis on Legal, Financial, and Supply Chain integrations. Write and optimize SQL/PL-SQL and custom scripts (Java/Groovy/JavaScript/Python); manage code via Git/GitHub; provide production support and on-call as needed. Partner with Legal, Compliance, and IT stakeholders to gather requirements and translate them into working integrations. Experience: 6–8 years of integration/automation experience, with hands-on Workato and Boomi. 4–6 years building and managing APIs (API Gateway, OAuth/SAML/JWT) and SFTP-based file transfers. 2+ years supporting Legal systems integrations (CLM, e-signature, matter management, c

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. About Okta Secures AI Team The Okta for AI Agents Team is building the future of digital identity management. The way companies are using agents and allowing them access is undergoing a fundamental shift, enabling teams to move fast while staying secure. Our North Star is clear: To get AI right, you have to get identity right. We are not just managing identities; we are building the industry's first Identity Security Fabric for the agentic era. As organizations rapidly deploy AI, these non-human entities are acting with access to critical tools, often bypassing traditional perimeters and creating a 'Shadow AI' crisis. Our mission is to move identity from a reactive gatekeeper to a unified control plane, transforming AI risk into business ROI. We are tackling this by implementing a comprehensive four-pillar maturity model: Discover, Onboard, Protect, and Govern. We are driving innovation by defining the standards for Agentic Identity—including pioneer work with securing AI Agents and support for protocols like MCP. You will be helping us build the infrastructure that allows enterprises to scale AI safely, ensuring every access decision—whether made by a human or an automated agent—is authenticated, authorized, and audited at scale. We are a diverse team of engineers, product managers, and designers who are bringing Okta’s expertise in identity to define the future of Agent Identity management, focusing on enablement while staying secure. About the role