Senior Lead Finance Operations at Upwork

This role is designed for a strategic finance professional with 7–10 years of experience who specializes in the intersection of finance and technology infrastructure. The ideal candidate has a deep understanding of cloud economics and the specific costs associated with AI development, such as GPU workloads and LLM providers. You’ll need to be comfortable acting as a "translator" between engineering teams and executive leadership, turning complex technical usage into clear ROI frameworks. The compensation is a major standout, offering an annual base salary range of **$150,500 – $235,500 CAD**, plus eligibility for bonuses and equity. While the role starts as full-time hybrid in Toronto, there is a unique structural element: you will initially be employed through a partner while the Toronto hub is built out, with the intent to transition directly to the company by 2026. This is a high-impact position where you will directly influence how one of the world’s largest talent marketplaces scales its AI capabilities. **You might be a good fit if you...** * Have mastered driver-based modeling for AWS, Azure, or GCP and understand "showback" reporting. * Can build an investment case or ROI model for high-stakes AI training and inference costs. * Enjoy "influencing without authority" by partnering with Product and Engineering leaders. * Live in (or are willing to commute to) Toronto 3 days a week.