Chief of Staff to the COO & GM of Marketplace

Upwork•Palo Alto, CA

2d•Remote

About The Position

Upwork Inc. is seeking a Chief of Staff to the COO & GM of Marketplace. This role is a senior, strategic position that acts as a true operating partner, extending the COO's capacity, sharpening decision-making, and holding together a complex, fast-moving organization. The Chief of Staff will be a trusted thought partner, responsible for preparing the COO for high-stakes conversations, owning the operating rhythm of the COO organization, and ensuring clarity and execution across key initiatives. This role also involves modeling leadership values, acting as a connective tissue between strategy and execution, and providing stability during organizational change. The ideal candidate will have operated at the intersection of strategy and execution in a high-velocity environment and possess strong organizational, communication, and judgment skills.

Requirements

Operated at the intersection of strategy and execution in a high-velocity environment (e.g., consulting, investment banking, high-growth tech company).
Understanding of how businesses work, how organizations behave under pressure, and how to move complex stakeholders without formal authority.
Exceptional organizational skills that instill confidence and prevent things from falling through the cracks.
Ability to think clearly under ambiguity.
Excellent written and verbal communication skills.
Ability to build a compelling deck and the strategy behind it.
Discretion and judgment to act as a confidant, being discreet with sensitive information, frank in private, and diplomatically effective.
Ability to be direct and patient as needed.
Earn trust through consistent high performance and integrity.
10+ years of relevant experience.
MBA or equivalent strongly preferred.
Prior Chief of Staff experience or a similar senior operating role is a plus.

Responsibilities

Serve as a trusted thought partner to the COO, surfacing risks, ensuring data-grounded decisions, and pushing back privately while representing the COO's point of view publicly.
Prepare the COO for high-stakes conversations, including drafting and driving board presentations, executive reviews, and cross-functional negotiations.
Own the operating rhythm of the COO organization, ensuring business reviews, planning cycles, and leadership forums are substantive, efficient, and connected to strategic priorities.
Work with finance and functional leads to ensure disciplined budget management and proactive trade-off decisions.
Identify and address fragmentation, decision gaps, and accountability issues within the COO's broad organizational portfolio.
Maintain a clear line of sight across key initiatives, ensuring the COO has the necessary information and context to drive outcomes.
Own the quality of materials presented to the COO, provide feedback to senior leaders, and protect executive time.
Unblock cross-functional friction that stalls important initiatives by convening the right people, clarifying decision rights, and escalating or resolving issues as needed.
Model leadership values and act as a connective tissue between strategy and execution.
Provide stability and continuity during organizational transitions or change periods.