Ai Senior Systems Engineer in Toronto

About Clutch Clutch is Canada's largest online used car retailer, delivering a seamless, hassle-free car-buying experience to drivers everywhere. Customers can browse hundreds of cars from the comfort of their home, get the right one delivered to their door, and enjoy peace of mind with our 10-Day Money-Back Guarantee. Named one of Canada's Top Growing Companies two years in a row and awarded a spot on LinkedIn's Top Canadian Startups list, we're looking to add curious, hard-working, and driven individuals to our growing team. Headquartered in Toronto, Clutch was founded in 2017. Clutch is backed by world-class investors including Canaan, BrandProject, Real Ventures, D1 Capital, and Upper90. To learn more, visit clutch.ca Technology Full TypeScript stack for front- and back-end, with some legacy JavaScript Front-end: ReactJS app with functional components and context API Back-end: ExpressJS with PostgreSQL database and Sequelize ORM Microservices architecture using Docker, Terraform, AWS ECS, and other AWS services Interservice communication via RabbitMQ and Apache Kafka About the role Clutch is seeking a Team Lead, Software Engineering to lead a team of engineers building and scaling our platform. This is a player-coach role: you'll split your time roughly evenly between hands-on engineering and team leadership, mentoring engineers, owning team delivery, and partnering with product to ship work that moves the business forward. You'll partner closely with other engineering leaders on technical direction and cross-team initiatives while owning the health, growth, and execution of your team. What you'll do Lead a team of 3–5 engineers, owning their growth, performance, career development, and day-to-day delivery Stay hands-on, contributing roughly half your time to code, architecture, and technical design across the stack Partner with Product, Design, and Data to translate business priorities into a clear roadmap and well-scoped engineering work Drive execution and de

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

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