Technical Support Engineer 2 in Toronto

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

Overview: Qsight is a high-growth division of Guidepoint focused on building data intelligence solutions for the healthcare sector. Qsight leverages proprietary datasets and rigorous analysis of alternative data sources to generate actionable insights for top-tier institutional investors, medical device manufacturers, and pharmaceutical companies. The Qsight team develops market intelligence products designed to be highly relevant, accurate, and scalable – delivering superior insights to a diverse, global client base. We are seeking an experienced, motivated Tehnical Operations Engineer to join our growing team. This is a multiple-hats role focused on SaaS/platform operations and tier-2 support for client-facing systems. You will own the administration and reliability of key tools, troubleshoot and resolve escalations with clear documentation, and build lightweight automation and reporting to reduce manual work as we scale. You will partner closely with Customer Success, Product, and Engineering to proactively monitor, support, and improve critical systems. Through practical, creative problem-solving, you will strengthen reliability, accelerate time to resolution, and increase operational visibility. Day to day, you will triage and resolve client technical questions, manage vendor license administration and renewals, and produce reporting that informs operational decisions. This role is a launchpad toward an SRE/Platform Engineering track as you grow into deeper automation, reliability engineering, and systems design work. This is a hybrid position based out of our Toronto office. What You’ll Do: Platform Support Own routine ops and configuration changes for critical SaaS platforms – Including Tableau, Freshdesk, Datadog, and our own client facing and internal portals Configure and maintain Freshdesk portals, routing, SLAs, permissions, integrations, etc. based on business requirements. Automate manual operations with Python, PowerAutomate, and shell scri

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. With over half a billion rides and counting, Lyft is solving hard problems in a flourishing domain with a lot of data and creative solutions in Marketplace, Mapping, Fraud, Growth and beyond. We're actively building the next-generation Machine Learning (ML) platform for low-cost, ultra-immersive transportation to improve people’s lives using modern ML with peta-byte scale data. Our Machine Learning Engineers are excited to work on these challenging problems and redefine solutions to directly impact various aspects of Lyft's primary business. If you are a student with experience in machine learning workflows, passionate about solving challenging problems using data and working in a dynamic, creative, and collaborative environment, this opportunity is for you! Responsibilities: Contribute to the design, build, train and test of Machine Learning models Write production-level code to convert ML models into working pipelines Partner with Product Managers, Data Scientists, and fellow ML Engineers to frame Machine Learning problems within the business context Analyze experimental and observational data, communicate findings to support decisions Participate in code and spec reviews to ensure code quality and distribute knowledge Experience: Currently pursuing a Bachelor's, Master's, or PhD degree in Computer Science or a related technical field from a university in Canada (required) , with a graduation date between December 2027 and Summer 2028 (required). For any candidates who are master's students who worked between their bachelor's and master's programs: candidates should also have less than 2 years of relevant full-time work experience Available during Summer 2027 for the internship in Toronto Good understanding and knowledge of ML libraries like scikit-learn, Tensorflow, PyTorch, Keras, MXNet, et

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 team The Billing team sits at the intersection of product, finance, and infrastructure. They're responsible for ensuring every observable event—errors, logs, traces, tokens—gets accurately measured, priced, and billed. Their work directly impacts company revenue and customer trust, requiring distributed systems expertise, attention to financial accuracy, and deep understanding of product usage patterns. The team works cross-functionally with product, engineering, BizOps, marketing, and sales to build systems that enable new products and pricing models. About the role As a Senior Software Engineer, you will architect and scale the core systems that power Sentry's billing infrastructure, ensuring accuracy and reliability at massive scale. You will collaborate on building the next generation of Sentry’s usage tracking pipeline, processing hundreds of billions of events daily with low latency and financial-grade accuracy. You will help design flexible pricing primitives that support everything from per-event usage billing to complex enterprise contracts, enabling product and sales teams to experiment rapidly while maintaining revenue accuracy and reduced time-to-market for new products. You will contribute to technical decisions on data consistency challenges unique to billing—like handling event delays, retroactive pricing changes, and distributed count reconciliation across our infrastructure. You'll love this job if you Want to solve the "easy to explain, hard to build" problems—like ensuring a customer's bill matches their usage perfectly, even when processing hundreds of billions of events daily across distributed

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 The Security Team is responsible for securing all things Sentry: our customers, our code, and everything in between. We are a small but growing team with broad scope, high trust, and the autonomy to tackle hard security problems with creativity and an engineering mindset. We work at a company with a strong developer culture, building a product that millions of developers genuinely love and rely on. That context shapes everything about how we operate. As a Security Engineer on this team, you'll work across application and platform security domains. You'll contribute to the practices that keep Sentry secure as we grow: security reviews, threat modeling, vulnerability management, and embedding secure coding practices into an engineering organization that cares about doing things right. You'll partner closely with product and engineering teams to influence how features are designed and built from the start. You will work as a technical collaborator who helps make the secure path the obvious one. As Sentry expands our agentic product capabilities and development practices, you'll also find yourself at the frontier of a new set of security challenges. In this role, you will Support and help mature Sentry's security review program. From secure code review, to architecture review, and threat modeling. You'll help build the processes, tooling, and culture which make security a natural part of how we ship and operate. Contribute to mature vulnerability management practices. Intake, triage, prioritization, remediation tracking, and support of our bug bounty and responsible disclosure program. Advocate for secure-by-desig

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. Our ultimate goal is to be a leader in democratizing access to private and public equity markets by making those assets available on-chain and be tradable 24/7. As a Staff Software Engineer in this role, you will work on the most critical projects across Tokenization, Robinhood Chain, and the Robinhood Wallet. Most importantly, you will proactively coach and uplift other team members, drive engineering excellence, and set the highest bar for quality. This role is based in our Toronto office, 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 do Own the technical vision and execution for Robinhood Chain, the Tokenization Engine, and the Robinhood Wallet Design, build, and operate the core services that power Robinhood Chain, the Tokenization Engine, and the Robinhood Wallet Remain deeply hands-on by writing production code, leading complex implementations, and setting the standard for engineering quality across the platform Improve

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: Sentry is expanding our Technical Customer Success team to support our growing customer base and drive deeper adoption of the Sentry Platform worldwide. As a Technical Customer Success Manager (TCSM), you’ll be a Sentry product expert responsible for ensuring customers are successfully onboarded, achieve maximum value from our platform, and uncover new opportunities for growth through additional use cases and products. You’ll play a key role in helping customers realize measurable outcomes with Sentry. In this highly cross-functional role, you’ll collaborate closely with Account Executives (AEs), Sales Engineers (SEs), and Engineering teams to ensure customers’ technical and business goals are met. This role requires strong technical expertise and a deep understanding of the Software Development Life Cycle (SDLC) and related technologies. If you’re a technologist with experience supporting technical products in customer-facing roles—and you’re eager to join a fast-growing team delivering real value through an exceptional product—we’d love to meet you. In this role you will: Become a Sentry product expert and support customers by understanding their needs and helping them achieve their goals using the Sentry Platform. Drive customer success and health through effective onboarding, adoption, value realization, and retention. Collaborate with customer key stakeholders to define business and technical objectives, and work with the customer team to achieve them. Act as a trusted, strategic advisor to each assigned customer—driving best practices, innovation, and long-term success. Partner closely with the sales te

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

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 We are seeking a proactive, customer-focused IT Support Specialist based in Toronto to anchor our regional IT operations. In this role, you will be the primary point of contact for internal employees, delivering white-glove technical support while managing core identity, collaboration platforms, and SaaS systems. Beyond day-to-day helpdesk operations, this position bridges traditional IT support and modern systems engineering. You will leverage automation, scripting, and modern DevOps practices to streamline user lifecycles, eliminate manual toil, and ensure our workforce operates securely and efficiently. Key Responsibilities Serve as the first point of contact for internal employees, triaging incoming requests through the ticketing system and established support processes. Troubleshoot and resolve workstation, laptop, mobile, and basic network issues for on-site staff and remote employees, escalating more complex support cases to senior staff or the appropriate team. Deliver calm, clear support during high-priority incidents, keep users informed, and document work thoroughly through to resolution. Manage end-to-

Want to work in technology at an investment bank? Graduate training, ongoing support, opportunities at leading global employers – the Alumni graduate program gives you everything you need. (And don’t worry, there’s no training bond. No exit fees, no hidden catches).Here at mthree, we pair great graduates with brilliant global businesses. Our clients include tier one investment banks and other organizations across a range of industries, from insurance to healthcare to travel.This is an exciting opportunity to join an FX Front Office support team in a major North American bank working on the Toronto Trading floor, supporting both front office users and a progressive eFX programme. What you'll do: Support IT solutions for various business lines globally including FX, Money Market, STIR and Options Offer technical expertise and support for the systems used Manage and resolving incidents and outages Manage requests for changes, system releases and capacity planning Disaster recovery, planning and execution How the Alumni program works: Apply via this job advert. Complete our assessment process. Get trained at mthree Academy in an online class for 4-8 weeks with other graduates. Join a mthree client for 12-24 months while receiving support and salary increases every 9 months. The vast majority then convert to permanent employees with the client at the end of the program. What you’ll learn at the mthree Academy: How to discuss production support activity at a high level including ITIL (information technology infrastructure library), monitoring, DevOps, SRE (site reliability engineering), and disaster recovery. How to discuss common financial topics, including financial markets, equity trading, derivatives, currency, treasury, regulation, and risk. How to write a basic computer program in Python, including user input, common data structures, and flow of control. How to use MySQL to perform CRUD (create, read, update and delete) operations on a relational database stored in

Want to work in technology at an investment bank? Graduate training, ongoing support, opportunities at leading global employers – the Alumni graduate program gives you everything you need. (And don’t worry, there’s no training bond. No exit fees, no hidden catches).Here at mthree, we pair great graduates with brilliant global businesses. Our clients include tier one investment banks and other organizations across a range of industries, from insurance to healthcare to travel.This is an exciting opportunity to join an FX Front Office support team in a major North American bank working on the Toronto Trading floor, supporting both front office users and a progressive eFX programme. What you'll do: Support IT solutions for various business lines globally including FX, Money Market, STIR and Options Offer technical expertise and support for the systems used Manage and resolving incidents and outages Manage requests for changes, system releases and capacity planning Disaster recovery, planning and execution How the Alumni program works: Apply via this job advert. Complete our assessment process. Get trained at mthree Academy in an online class for 4-8 weeks with other graduates. Join a mthree client for 12-24 months while receiving support and salary increases every 9 months. The vast majority then convert to permanent employees with the client at the end of the program. What you’ll learn at the mthree Academy: How to discuss production support activity at a high level including ITIL (information technology infrastructure library), monitoring, DevOps, SRE (site reliability engineering), and disaster recovery. How to discuss common financial topics, including financial markets, equity trading, derivatives, currency, treasury, regulation, and risk. How to write a basic computer program in Python, including user input, common data structures, and flow of control. How to use MySQL to perform CRUD (create, read, update and delete) operations on a relational database stored in

Engineering Manager, AI Conversation Platform 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 newly formed Conversation Platform team aims to build a conversation platform for all merchants who use Stripe. We are doing so by (a) automating the easy tasks, and (b) assisting our users in the difficult tasks. Some examples include customizing the Stripe landing page to suggest bespoke integrations, allowing users to command the Stripe API in natural language, and resolving user issues automatically. We are developing RAG based systems on the latest LLMs as well as fine-tuning our own models. We’re an end-to-end team going from ideas to models to shipping in production. What you’ll do Responsibilities Driving an ambitious vision for AI/ML that benefits our users Setting the technical & process direction for the team based on business goals Brainstorm and coordinate product integrations with partner teams Proposing new ideas and building prototypes Be an integral part of a larger ML community internally & externally Hire & develop a world-class team to deliver high-quality ML systems. Coach engineers to help them grow in their careers and maintain a high bar Who you are We are looking for ML Engineering Managers who are passionate about using ML to improve products and delight customers. You have experience leading teams that develop streaming feature pipelines, build ML models, and deploy them to production, even if it involves making substantial changes to backend code. You a

Engineering Manager, AI Conversation Platform 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 newly formed Conversation Platform team aims to build a conversation platform for all merchants who use Stripe. We are doing so by (a) automating the easy tasks, and (b) assisting our users in the difficult tasks. Some examples include customizing the Stripe landing page to suggest bespoke integrations, allowing users to command the Stripe API in natural language, and resolving user issues automatically. We are developing RAG based systems on the latest LLMs as well as fine-tuning our own models. We’re an end-to-end team going from ideas to models to shipping in production. What you’ll do Responsibilities Driving an ambitious vision for AI/ML that benefits our users Setting the technical & process direction for the team based on business goals Brainstorm and coordinate product integrations with partner teams Proposing new ideas and building prototypes Be an integral part of a larger ML community internally & externally Hire & develop a world-class team to deliver high-quality ML systems. Coach engineers to help them grow in their careers and maintain a high bar Who you are We are looking for ML Engineering Managers who are passionate about using ML to improve products and delight customers. You have experience leading teams that develop streaming feature pipelines, build ML models, and deploy them to production, even if it involves making substantial changes to backend code. You a

About the Team: Tubi's Internal Tools team is at the forefront of AI integration, developing everything from developer resources to production-grade AI for business operations. We are the group responsible for turning AI from an experiment into an operating capability: training, infrastructure, developer agents, and AI-powered business systems. Engineers operate with high ownership and autonomy, collaborating on shared architectural decisions and AI infrastructure. What You'll Do: Own systems end to end — design them, build them, and support them in production. Lead the projects you own: sequence the work, decide what lands first, and set technical direction for the engineers working with you. Sit with the people who use what you build, and turn what you learn there into a system. Design the service boundaries, contracts and schema evolution that let our platforms grow without breaking the teams depending on them. Make our AI systems dependable in production: evaluation harnesses, human approval steps before an agent acts, retries that handle a model returning something unexpected, and cost tracking that tells you what a task costs before you run it. Build what other engineers build on — agent skills, tool and MCP integrations, shared libraries — and raise the bar through code review, design discussion and mentoring. Spot the platform work nobody has asked for yet, make the case for it, and build it. Your Background: 5+ years of professional experience building and operating production systems, from design through production ownership. A system you designed and can walk us through end to end — where its boundaries sit, what constrained it, and what you chose against. Strong programming proficiency in a statically typed language such as Rust, Go, C++, Java, Kotlin, C#, or TypeScript. Production Rust is a plus rather than a requirement. You have owned a service in production: you wrote the runbooks, you knew what it cost, and you were the one paged when it broke. Expe

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. Lyft is looking for an IT Systems Engineer to lead the technical side of integrating newly acquired companies into Lyft's IT environment. You'll be responsible for migrating collaboration tools, SaaS platforms, and identity systems from acquired teams into Lyft's stack, with minimal disruption to either side. We're looking for a self-starter who's equally comfortable driving projects independently and partnering with others to get things done. The ideal candidate brings strong attention to detail, creative problem-solving, and a genuine drive to automate processes and improve efficiency across the IT organization. Responsibilities: Manage SaaS integration and consolidation during merger and acquisition activity, ensuring smooth platform migrations, data integrity, and minimal disruption across merged organizations Provide architectural, engineering, and operational support for corporate IT systems at Lyft Support single sign on integrations with Lyft’s primary identity provider, Okta. Leverage various APIs to write scripts and applications to automate IT Operations Support and work with IT, Security and other internal departments by building automation for repetitive tasks Write detailed and concise documentation and runbooks Engage with vendors to implement and improve services to best support Lyft’s needs Be a mentor to others in IT and act as a source for others Experience & Skills: 5+ years of experience managing corporate IT Systems Proven experience supporting IT integration during mergers, acquisitions, or divestitures, including SaaS platform consolidation and system migrations SaaS system application management including but not limited to: Gsuite, Okta, Atlassian, Slack Scripting experience leveraging GAM, Python, Bash, and/or equivalent tools Comfortable consuming RES