Chief of Staff to the COO & GM of Marketplace

Upwork•Palo Alto, CA

2d•$229,000 - $384,000•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 to the COO, extending their capacity, sharpening decision-making, and holding together a complex, fast-moving organization. The COO's portfolio spans Legal, Information Security, Marketing, Payments, Trust & Safety, Communications, Customer Support, Design, and Product. The Chief of Staff will be a trusted thought partner, prepare the COO for high-stakes conversations, own the operating rhythm of the COO organization, ensure operational integration, drive execution and clarity across key initiatives, and model leadership values. This role requires someone who can operate at the intersection of strategy and execution in a high-velocity environment, possess exceptional organizational skills, think clearly under ambiguity, communicate with precision, and exercise discretion and judgment.

Requirements

Operated at the intersection of strategy and execution in a high-velocity environment (consulting, investment banking, high-growth tech company, or combination).
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.
Ability to write and communicate with precision.
Ability to build a compelling deck and the strategy behind it.
Discretion and judgment to be a confidant, discreet with sensitive information, frank in private, and diplomatically effective.
Ability to be direct and patient.
Earn trust by consistently being great at the job and acting with 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, making every interaction with the COO more valuable by surfacing risks, ensuring data-grounded decisions, pushing back privately, and 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, presenting options and a point of view.
Own the operating rhythm of the COO organization, ensuring monthly and quarterly business reviews, annual planning cycles, and leadership forums are substantive, efficient, and connected to strategic priorities.
Work directly with finance and functional leads to ensure budget discipline and proactive trade-off decisions.
Identify and address fragmentation, breakdown in alignment, falling decisions, and reinforce accountability across the COO's broad portfolio.
Maintain a clear line of sight across key initiatives, ensuring the COO has the necessary information, context, and preparation 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 knowing when to escalate versus resolve.
Model leadership values, act as connective tissue between strategy and execution, and provide stability and continuity during organizational transitions.