Chief of Staff to GM & Chief Operating Officer

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 . Upwork's COO and GM of Marketplace operates across one of the broadest organizational portfolios in the company - spanning Legal, Information Security, Marketing, Payments, Trust & Safety, Communications, Customer Support, Design, and Product. The Chief of Staff to the COO exists to make that model work: not as a coordinator, but as a true operating partner who extends the COO's capacity, sharpens decision-making, and holds together a complex, fast-moving organization. This role requires someone who has earned the confidence to walk into any room, speak with authority, and immediately earn credibility - with the COO's direct reports, with the executive team, and with external stakeholders. It is a senior, strategic seat, and will be treated as one. Responsibilities: Strategic Partnership Serve as a trusted thought partner - not as a gatekeeper, but as someone who makes every interaction with the COO more valuable. You will be the person the COO thinks out loud with, who surfaces risks before they become problems, and who ensures decisions are grounded in the right data and framing. You will push back privately, represent the COO's point of view publicly, and discern between the two like it was remembering to breathe. Prepare the COO for high-stakes conversations - drafting and driving board presentations, executive reviews, cross-functional negotiations - surfacing not just what is known, but what remains ambiguous or contested. Where there's a decision to be made, you'll come with options and a point of view, not just a summary. Operational Integration Own the operating rhythm of the COO organization. Monthly and quarterly business reviews, annual planning cycles, leadership forums - you will ensure these are substantive, efficient, and connected to strategic priorities rather than calendar obligations. You'll work directly with finance and functional leads to ensure budget is managed with discipline and that trade-off decisions are made proactively, not reactively. Across a portfolio this wide, fragmentation is the enemy. You will identify where alignment is breaking down, where decisions are falling through the cracks, and where accountability needs to be reinforced - and you will fix those things without waiting to be asked. Execution and Clarity Maintain a clear line of sight across key initiatives and ensure the COO has the information, context, and preparation needed to drive outcomes - not just attend meetings. You will own the quality of materials that come to the COO, provide direct feedback to senior leaders preparing those materials, and ensure that executive time is protected…