Senior Lead Finance Operations at Upwork

This role is ideal for a seasoned finance professional (7–10 years experience) who sits at the intersection of FP&A and Engineering. You should be a "FinOps" specialist who understands the high costs associated with AI—specifically GPU workloads, LLM providers like OpenAI, and cloud infrastructure. If you enjoy building complex ROI models for technical products and can translate "server speak" into executive financial narratives, this is for you. The compensation is highly competitive ($150.5k – $235.5k CAD) and includes bonus and equity eligibility. This is a foundational hire for a new operational hub in Toronto, offering the chance to help build out the company’s local presence. Note the unique employment structure: you will initially be employed through a partner before potentially transitioning to a direct hire once the Toronto office is fully established by late 2026. **You might be a good fit if you...** * Have deep experience managing cloud economics (AWS/GCP/Azure) and AI-specific infrastructure costs. * Can build driver-based models that connect engineering roadmaps to long-range financial forecasts. * Comfortable working in a hybrid environment (3 days in-office) in Toronto once the hub opens. * Are skilled at "influencing without authority" when partnering with Engineering and Product leads to optimize spend.