Chief of Staff to COO and GM of Marketplace

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. 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. Represent the COO's point of view publicly and discern between the private and public facets of that perspective. 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. When a decision must be made, 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 – ensure these are substantive, efficient, and connected to strategic priorities rather than calendar obligations. Work directly with finance and functional leads to ensure the budget is managed with discipline and that trade‑off decisions are made proactively. Across a portfolio this wide, fragmentation is the enemy. Identify where alignment breaks down, where decisions fall through the cracks, and where accountability needs to be reinforced – and 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. 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 for the work that only the COO can do. When cross‑functional friction stalls something important, unblock it. Convene the right people, clarify decision rights, and decide when to elevate versus resolve. Culture and Continuity Model the leadership values Upwork expects of its people. Be the connective tissue between strategy and execution – translating intent into direction for a team that operates across remarkably diverse functions. During transitions or periods of organizational change, be the source of stability and continuity. Qualifications Have operated at the intersection of strategy and execution in a high‑velocity environment – consulting, investment banking, a high‑growth tech company, or some combination. Understand how businesses work, how organizations behave under pressure, and how to move complex stakeholders without formal authority. Be organized in a way that others notice – instilling confidence that things do not fall through the cracks, and that people know you are dependable. Think clearly under ambiguity, write and communicate with precision, and can build a compelling deck and the strategy behind it in the same sitting. Have the discretion and judgement to be a confidant – discreet with sensitive information, frank in private, and diplomatically effective in every setting. Know when to be direct and when to be patient. Earn trust by consistently performing well and acting with integrity. Have 10+ years of relevant experience; an MBA or equivalent strongly preferred. Prior Chief of Staff experience or a similar senior operating role is a plus, but the profile matters more than the title. Benefits Comprehensive medical coverage for you and your family. Unlimited paid time off. 401(k) plan with matching. Twelve weeks of paid parental leave. Employee Stock Purchase Plan. Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, age, status as a protected veteran or as an individual with a disability, genetic information, or other legally protected characteristics under federal, state or local law. #J-18808-Ljbffr Upwork