Senior Lead Finance Operations

About the Position

Join Upwork as a Senior Lead Finance Operations to drive financial forecasting, cost optimization, and strategic investment frameworks in a dynamic AI-driven business environment.

Responsibilities

• Drive the monthly, quarterly, and long-range forecasting for cloud and hosting expense
• Build and maintain driver-based models for AI workloads (Training vs. Inference), connect product roadmaps, usage assumptions, and infrastructure demand to financial plans
• Lead monthly forecast process for capitalized labor (IDSW capitalization); partnering with Accounting and Engineering to track initiative alignment and ensure project-level visibility
• Identify and drive efficiency opportunities across cloud and GPU spend through utilization optimization, capacity planning, and pricing levers
• Establish financial guardrails for AI and infrastructure investments to balance spend discipline with innovation and long-term growth
• Deliver vendor showback reporting to surface utilization insights, partnering with Strategic Sourcing on tool rationalization and contract optimization
• Establish baseline ROI metrics for AI and SMB investments, defining "fully burdened" costs per initiative/product
• Develop scalable frameworks for evaluating incremental investment trade-offs, providing leadership with insights on payback and resource allocation
• Partner with the business to build investment proposals that justify and prioritize high-stakes strategic initiatives
• Prepare executive-ready materials for QBRs, leadership reviews, and long-range planning
• Translate complex technical and financial concepts into clear narratives, recommendations, and decision options
• Act as a thought partner to Finance leadership in scaling FinOps capabilities as the business grows

Requirements

• 7-10 years in FinOps, Strategic Finance, or FP&A, with experience supporting Product, Engineering, Infrastructure, or AI-driven businesses
• Deep understanding of cloud economics, GPU-intensive workloads, and the cost levers of LLM providers (OpenAI, Anthropic, etc.)
• Proven ability to build driver-based models that connect technical inputs to financial outcomes
• Experience developing unit economics, ROI frameworks, and investment evaluation models
• Excellent business partnering with engineering and product teams to provide financial analysis and insights to critical strategic decisions, able to influence without authority and challenge assumptions constructively
• Strong executive storytelling skills, comfort translating complex engineering concepts into simple financial narratives
• Ownership mindset with a bias toward action and accountability

We Offer

• Competitive salary range: $150,500 - $235,500 CAD per year
• Opportunity to work in a new operational hub in Toronto, Canada
• Hybrid work location type
• Comprehensive benefits package offered by our partner

About the Company

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. Join us in revolutionizing work and building agile teams.

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.

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.

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