Complex Head in Toronto

Overview: Guidepoint seeks an experienced AI Engineer as an integral member of the Toronto-based AI team. The Toronto Technology Hub serves as the base of our Data/AI/ML team, dedicated to building a modern data infrastructure for advanced analytics and the development of responsible AI. This strategic investment is integral to Guidepoint’s vision for the future, aiming to develop cutting-edge Generative AI and analytical capabilities that will underpin Guidepoint’s Next-Gen research enablement platform and data products. This role demands exceptional leadership and technical prowess to drive the development of next-generation research enablement platforms and AI-driven data products. You will develop and scale Generative AI-powered systems, including large language model (LLM) applications and research agents, while ensuring the integration of responsible AI and best-in-class MLOps. The AI/ML Engineer will be a primary contributor to building scalable AI/ML capabilities using Databricks and other state-of-the-art tools across all of Guidepoint’s products. Guidepoint’s Technology team thrives on problem-solving and creating happier users. As Guidepoint works to achieve its mission of making individuals, businesses, and the world smarter through personalized knowledge-sharing solutions, the engineering team is taking on challenges to improve our internal application architecture and create new AI-enabled products to optimize the seamless delivery of our services. This is a hybrid position based in Toronto. What You'll Do: Architect and Build Production Systems: Design, build, and operate scalable, low-latency backend services and APIs that serve Generative AI features, from retrieval-augmented generation (RAG) pipelines to complex agentic systems. Own the AI Application Lifecycle: Own the end-to-end lifecycle of AI-powered applications, including system design, development, deployment (CI/CD), monitoring, and optimization in production

Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond. Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn , Facebook , Instagram , TikTok , and X ; and learn more about Lifted at Go-Lifted and follow on LinkedIn . As a Senior People Operations Specialist, you will play a key role in delivering thoughtful, scalable people programs and operational support across the employee lifecycle. As part of our People Operations team, you’ll combine strong operational expertise with the judgment and partnership skills needed to support HR Business Partners, managers, and employees through both day-to-day needs and more complex people matters. You’ll own and continuously improve key people programs and processes, with a particular focus on employee lifecycle operations, immigration

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. The Tokenization team's mission is to bring both public and private equity to be tradable 24/7 on decentralized exchanges (DEXs) across the Robinhood Chain. We work at the intersection of blockchain technology, financial market infrastructure, and modern distributed systems - with a focus on accessibility, security, and scalability. Equity markets have been closed nights and weekends for a century; we're building the infrastructure that changes that. As a Senior Software Engineer , you will design and build the core systems that issue, custody, and settle tokenized equities on-chain and keep them in sync with traditional brokerage and ledger systems. You'll lead technically complex projects end to end, make architectural decisions on a foundational Robinhood initiative, and work in a domain where correctness is non-negotiable - the systems you build move real customer assets, continuously, across multiple chains and jurisdictions. This role is based in our Toronto, ON 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

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. The Margin Team is a high-leverage product engineering team building sophisticated investing and trading experiences for our most active users. Driving 100s of millions in revenue, the team provides the critical tools customers need to successfully manage their investments. Our primary offering –margin– has scaled to over $15B in usage and remains one of the fastest-growing revenue streams at Robinhood. Our team works closely with product, design, data, and partner engineering teams to make a complex financial product feel clear, intuitive, and trustworthy. As a Web Developer on this team, you would help build and scale customer-facing web experiences for Robinhood Crypto, contributing to products that support international users from onboarding through trading and funding. You would partner closely with product, design, and cross-functional engineering teams to ship high-quality features, support the launch of the web app in new markets, and help create safe, seamless crypto experiences as the platform expands. This role is based in our Toronto, ON office, with in-person attendance expected at least 3 days per week. At Robinhood, we believe in the power of in-person w

Who We Are At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people. We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you. We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team. Our Values If this sounds like you, you’ll fit right in. Who You Are You are self-driven and like to work with others to remove roadblocks. You are curious, and love to explore and learn new technologies. You have demonstrated the ability to build, deploy and maintain large-scale, complex applications. You care more about solutions and impacting the customer experience than using a particular tool or framework. Your Success Profile What You Will Work On As a part of the Workforce Management team, you will drive our expansion into exciting new verticals, enriching our platform to attract and delight new customer segments. Your mission will be to architect and deliver foundational solutions in the Applicant Tracking Systems (ATS), Contractor, and Expenses domains. Our specialized product pods focus on building lean, high-impact features for customers who want a streamlined experience without the overhead of a bloated platform. You'll join the expenses pod in Toronto and help build the platform that handles expense submissions, approvals, and reimbursements for Justworks customers. Working alongside 3-4 senior engineers, you'll contribute to our migration from Ruby to Go, build AI-powered features, a

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. Marketplace teams are at the heart of our products and decision-making, owning everything from rider pricing to driver earnings, incentives, and efficient matching. We’re looking for passionate, driven engineers to build systems that empower our riders and drivers to have the best transportation experience possible through prediction, adaptivity, and personalization. We’re looking for someone who is excited about working in a fast-paced, innovative, and impactful environment to create reliable solutions to distributed computing, ML, and data problems. The Pricing team is a centerpiece of Lyft’s Marketplace org, determining prices for all rideshare products and supporting new initiatives. Rider Engagement develops rider-facing engagement levers and optimizes user pricing experience to drive both short term and long term business outcomes. We work with Product & Science to solve and implement complex pricing requirements, balancing the needs of riders, drivers, and the business goals. As an owner of one of the most critical flows in the company, you will work on a wide array of challenges such as latency-sensitive concurrency problems, large scale distributed systems, and experimentation. If you’re interested in playing a large part in demand / supply management and improving the Lyft customer experience, this could be a great fit for you. Responsibilities: Drive high-impact projects and innovate new solutions to provide the best user experience. Work closely with cross-functional teams and partner teams to develop solutions based on technology and business needs, and advance team’s goals and priorities Independently lead features from idea to positive execution and launch Unblock, support and communicate with internal partners to achieve results Write well-crafted, well-tested, readable, maintaina

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 software engineers from a scope of disciplines. We are growing our team with people who want to build, improve and incorporate technologies that make the lives of our community more enriched. As an engineer at Lyft, you'll collaborate with teams like product, data science, analytics, and operations on code that empowers us to iterate quickly, while focusing on delighting our passengers and drivers. The Applied AI team is looking for a senior software Engineer to join the Recommendations team. You will build the backend systems that decide what we surface to riders. You will architect the pipelines and services that turn rider context and signals into the right offer at the right moment, driving a measurable impact on rider experience. Responsibilities: Establish engineering best practices and patterns; help uplift the team's craft and drive a culture of engineering excellence Drive high-impact projects and innovate new solutions to deliver the best user experience Produce and drive scalable system design for large, complex features — from idea through execution and launch Mentor engineers on the team, providing technical guidance and supporting their growth Champion and evangelize the use of AI tools to accelerate engineering productivity across the team, sharing patterns and best practices that raise the bar for how the team builds Write well-crafted, well-tested, readable, maintainable code Participate in code reviews to ensure code quality and share knowledge across the team Participate in the team's on-call rotation; identify, triage, debug, and resolve issues across our applications and platforms Excellent communication skills and the ability to explain the various trade offs made in decisions Manage project priorities, deadlines, and deliverables. Experience: BS/MS or

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 Issue Workflow is Sentry's primary product surface. Our issue platform processes billions events daily and turns them into actionable insights that help millions of developers fix bugs faster. As a Staff Software Engineer on the Issue Workflow team, you'll architect the systems that power this experience. You'll work at the intersection of high-scale distributed systems and product engineering, building real-time data pipelines, search backends, and analysis systems that surface signal from noise. This is product engineering at massive scale—where every architectural decision impacts millions of debugging sessions. You'll be the technical leader who shapes how Sentry groups issues, how we make search lightning-fast, how we enable sophisticated agentic workflows, and how we ensure that the product is performant even at billions-of-events scale. Your work will define what's possible for the most trafficked part of Sentry's platform. In this role you will Drive technical strategy and roadmap. Partner with engineering leadership, product, and design to shape the multi-quarter technical vision for Issue Workflow platform. Make strategic calls about architectural direction, technology choices, and technical debt. Ensure the team is building a strong foundation to scale with Sentry's growth. Solve complex performance and scalability challenges. Champion product quality and user experience. Build features that don't just work—they delight. You understand that milliseconds matter in the developer experience. You sweat the details of interfaces, error messages, loading states, and edge cases. You instrument everything s

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

We are looking for a Lead, Data Development, AI Platform to lead the team building and operating the technical platform behind Hootsuite's Analytics MCP. This includes routing infrastructure, orchestration services, agent infrastructure, and data pipelines that enable reliable AI-driven analysis at scale. You will set technical direction for the team, strengthen engineering practices, and translate target architecture and integration standards into secure, production-grade systems that Data Analytics & AI teams can confidently build on. This is a hands-on technical leadership role. You will stay close to the code while owning delivery outcomes, engineering quality, and the team's culture of craft and accountability. You will develop strong, well-reasoned recommendations on how the platform and orchestration architecture should evolve, seek approval at the Senior Manager and Director level, and then guide the team through disciplined execution. You will also partner closely with AI Context & Integration and AI Data Architecture to ensure the platform, context layer, semantic layer, and downstream agent workflows operate as one coherent system. WHAT YOU’LL DO: Lead the design and delivery of the orchestration layer that connects the Analytics MCP platform across its most complex surfaces, including query execution across schemas and models, federated data access between the data warehouse and external source systems, and multi-step agent workflows for cross-functional business processes. Develop clear technical recommendations for platform and orchestration architecture evolution, align those recommendations with Senior Manager and Director-level direction, and guide the team through disciplined execution within the approved architecture. Own the operational reliability, scalability, quality, and observability standards for core Analytics MCP components, including routing and agent infrastructure. Guide the team to build and operate these systems to prod

This posting is for a future vacancy. We’re looking for a Senior Account Executive, Enterprise Sales to help us develop and close new business with larger enterprise customers within our landmark industries. You will work in a fast paced sales environment selling Hootsuite solutions to prospective customers. This role is a full sales cycle role from opportunity creation to close. You will be responsible for owning your own pipeline and generating outbound opportunities with companies that could benefit from Hootsuite as their social media management partner. This is a hybrid role and is open to applicants located within commuting distance of our Vancouver or Toronto offices. In this role, you will report to the Manager, Enterprise Sales. WHAT YOU’LL DO: Successfully acquire new enterprise customers within our landmark industries in order to achieve and exceed individual quota targets. Develop and execute an industry-specific account growth strategy in order to identify, generate and develop a net new sales pipeline. Take ownership of your quarterly target by crafting and executing a strategy in order to identify, generate and develop net new sales pipeline and achieve/exceed quota targets. Accurately forecast sales activity and revenue attainment. Lead longer end to end sales cycles from value creation to negotiation and closing, and present the value of our solutions to senior and C-suite prospective customers. Lead strategic, high-impact conversations that uncover business priorities, align solutions to executive objectives, and drive long-term partnerships. Manage complex, global evaluations and manage stakeholders in different regions and departments. Proactively and strategically seek out market information and understand the product-market fit in order to effectively develop rapport with customers. As a subject matter expert in Social Media Management and in our customers unique industry, advise and recommend relevant solut

Who We Are At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people. We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you. We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team. Our Values If this sounds like you, you’ll fit right in. Who You Are Do you enjoy turning complex international employment issues into clear, practical guidance that helps teams move with confidence? Are you energized by helping a global EOR business handle sensitive employment lifecycle matters with sound judgment, consistency, and care? You are an experienced employment lawyer who understands that strong EOR legal support requires both legal judgment and operational follow-through. You know how to evaluate lifecycle risk, partner with local experts, align stakeholders, and help teams reach practical outcomes in complex and time-sensitive employment matters. You bring clear communication, business-oriented judgment, and a steady approach to sensitive employee lifecycle issues. As part of the International Legal team, the Senior Lifecycle Counsel, International will provide legal support for complex employment lifecycle execution across Justworks’ EOR offering, with particular focus on sensitive, complex, or escalated matters such as terminations, performance management, leave, and employee relations. You will serve as the legal point of contact for selected lifecycle matters that require Legal in

Who We Are At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people. We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you. We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team. Our Values If this sounds like you, you’ll fit right in. Who You Are You are self-driven and like to work with others to remove roadblocks. You are curious and love to explore and learn new technologies. You have demonstrated the ability to build, deploy, and maintain large-scale, complex applications. You care more about solutions and impacting the customer experience than using a particular tool or framework. About the role: You will join a small, highly autonomous cross-functional team to build AI agents that fundamentally transform how operations work at scale. Instead of writing bespoke software for every workflow, we are developing an agent platform that can read operational knowledge, reason about it in context, and execute tasks end-to-end. This approach allows us to scale complexity through knowledge and reasoning, rather than simply through code. This is an opportunity to join a foundational team, which currently consists of fewer than five engineers. The work spans critical areas including LLM-powered agent design, robust backend service architecture, tool and integration development, and sophisticated knowledge infrastructure. We are seeking a Senior Software Engineer with a strong pas

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . At Pinterest, we’re seeking curious, versatile Web Engineers to join our Product Engineering teams. You’ll work closely with product managers, designers, and backend engineers to continuously push the boundaries of what’s possible on the web—delivering delightful, cutting-edge experiences for millions of Pinners around the world. This is your opportunity to shape the future of inspiration—bringing bold product ideas to life, owning projects end to end, and driving innovations that empower both our users and fellow engineers. If you love solving complex problems, embrace new technologies, and care deeply about user experience, we’d love to have you onboard. What you’ll do: Build for Impact: Create and launch powerful, user-facing features for Desktop and Mobile Web that help spark creativity and inspire our global community. Full Product Ow

About Pinterest: Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product. Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the flexibility to do your best work. Creating a career you love? It’s Possible. At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI. Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process here . As an Industry Manager, you will define, launch and lead strategic outcomes and operationalize the vision for the sales team. We’re looking for a high-performing candidate with experience building advertising/media sales teams, working closely with technical cross-functional teams, a passion for solving complex problems, excellent written communication skills and the ability to influence at the executive level and globally. Our advertising business is thriving, our user base continues to grow, and we believe the impact of this role can fuel our company to grow in unprecedented ways. What you’ll do: Lead our sales strategy and execution for the Beauty and Luxury vertical. Partner with internal stakeholders to develop a sales strategy that enables Pinterest to win the market by meeting partner marketing objectives, scaling partner media investment