Senior Lead Finance Operations

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.

Responsibilities

Financial Ownership & Forecasting

• 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

Cost Optimization & FinOps Excellence

• 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.

Strategic Partnership & Investment Frameworks

• 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

Executive Communication & Reporting

• 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

What it takes to catch our eye

• 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

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.

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

$150,500—$235,500 CAD

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