Lead AI Engineer, NLQ & Agentic Systems at Upwork · Toronto

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 Lead AI Engineer on our Data Platform & Services (DPS) team, you will bridge deep data engineering expertise with emerging AI capabilities to build production-grade AI-powered systems. You’ll design and deploy agentic frameworks, natural language querying (NLQ) capabilities, and prompt/LLM evaluation strategies that unlock insights at scale across Upwork. This is an opportunity to deliver tangible impact, enabling faster decision-making, democratizing data access, and empowering analysts and stakeholders throughout the company. Responsibilities: Design and implement scalable agentic frameworks that coordinate multiple AI agents to deliver accurate and reliable outcomes. Build and optimize natural language query solutions that provide compliant, intuitive, and self-service access to enterprise data. Develop and maintain evaluation frameworks for LLMs and prompts, driving measurable improvements in accuracy, scalability, and resilience. Partner with data engineering peers to integrate AI orchestration with Python, SQL, and Snowflake pipelines. Contribute to AI-powered summarization and explanation tools that enhance reporting, insights, and executive reviews. Collaborate cross-functionally with product, analytics, and business teams to ensure solutions meet measurable business goals. What it takes to catch our eye: Proven experience delivering AI-powered data systems in production, including hands-on expertise with LLMs and prompt engineering. Strong foundation in modern data engineering, with proficiency in Python, SQL, and platforms such as Snowflake. Demonstrated ability to design agentic orchestration frameworks that scale across diverse business scenarios. A collaborative problem-solver with strong communication skills, able to align stakeholders and create clarity across teams. Growth mindset—excited to learn, iterate, and deliver measurable business outcomes through applied AI. Come change how the world works. Upwork is establishing an operational hub in Toronto, Canada. The new office is expected to be fully operational by Q4 2026. This role will require 3 days in office once we have an office open. This position will initially be employed through a partner to ensure a seamless hiring process while we establish the hub. Once the hub is established, there may be opportunities to transition to employment with Upwork, depending on business needs and other requirements. While employed by the partner, you’ll work as part of Upwork’s team, with access to our resources, culture, and growth opportunities. Our partner will offer competitive benefits. When Upwork’s hub is established, we will be excited to offer employment and benefits directly as business needs require. Upwork is committed to building a diverse, inclusive, and equitable workforce. Employment decisions are made without regard to race, color, religion, gender, sexual orientation, gender identity, national origin, disability, or any other status protected by applicable law. We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled. To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice and the Applicant Privacy Addendum (Canada). The annual base salary range for this position  is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program. Annual Base Compensation $179,000—$302,000 CAD To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice