Chief of Staff to GM & Chief Operating Officer

About the role

The Chief of Staff to the GM and Chief Operating Officer at Upwork serves as a strategic operating partner designed to extend the capacity and impact of the executive leadership team. This role owns the end-to-end operational integrity of the COO's organization, ensuring that complex, cross-functional initiatives move from discussion to decisive action. You will act as a trusted thought partner, pushing back privately and representing the COO's perspective publicly with equal conviction. The position requires earning immediate credibility across the executive suite and external stakeholders by combining rigorous analytical thinking with exceptional judgment. You will be responsible for making every interaction with the COO more valuable by surfacing risks before they escalate and framing decisions with clarity and precision. Ultimately, this role ensures that the broad portfolio of the COO, spanning marketplace operations, legal, security, finance, and customer support, functions as a cohesive, strategic unit rather than a collection of silos.

Key facts

What you'll do

• Serve as a trusted strategic thought partner to the COO, making every interaction more valuable by surfacing risks, framing decisions, and ensuring discussions are grounded in the right data and context.
• Own the operating rhythm of the COO organization by designing and driving monthly and quarterly business reviews, annual planning cycles, and leadership forums that are substantive, efficient, and tied directly to strategic priorities.
• Prepare the COO for high-stakes conversations by drafting and driving board presentations, executive reviews, and cross-functional negotiations, ensuring ambiguity and contested perspectives are surfaced alongside clear options and recommendations.
• Act as the central integrator of complex initiatives across the COO portfolio, identifying where alignment is breaking down, decisions are falling through cracks, and accountability is unclear, then intervening to fix these issues without waiting to be asked.
• Maintain a clear line of sight across key initiatives to ensure the COO has the information, context, and preparation needed to drive outcomes, not merely attend meetings, by synthesizing updates and anticipating implications.
• Work directly with finance and functional leaders to manage budget with discipline, proactively surface trade-offs, and ensure resource allocation is aligned with strategic priorities across Legal, Information Security, Marketing, Payments, Trust & Safety, Communications, Customer Support, Design, and Product.
• Represent the COO's point of view publicly while privately challenging assumptions and decision logic, discerning when to push back and when to advocate, ensuring consistency between internal counsel and external positioning.
• Identify and resolve fragmentation within the broad operational portfolio by strengthening communication pathways, clarifying decision rights, and reinforcing accountability structures across teams.
• Drive execution clarity by translating strategic priorities into actionable plans, tracking dependencies, and ensuring that leadership forums are focused on progress, risk mitigation, and informed decision-making.
• Partner with enterprise customers and stakeholders to understand evolving needs, translating feedback into internal alignment and ensuring the COO's leadership is equipped to respond with timely, coordinated solutions.
• Own special projects that require discretion, strategic judgment, and cross-functional influence, serving as a versatile resource to the COO and executive team.
• Ensure all operational practices, from planning rituals to decision frameworks, are continuously evaluated and refined to support scalability and speed in a fast-moving growth environment.
• Act as a bridge between the COO and the broader executive team, facilitating alignment, surfacing cross-functional dependencies, and ensuring shared ownership of outcomes.
• Maintain a rigorous prioritization framework to ensure the COO's attention is directed toward the highest-impact decisions and emerging issues that could alter the business trajectory.
• Support the development and communication of enterprise narratives that explain Upwork's market position, strategic choices, and operational performance to external audiences.

Requirements

• You are a seasoned executive operator with a track record of thriving in fast-paced, high-growth environments and managing complex, cross-functional portfolios.
• You have earned the trust and confidence of senior executives and can walk into any room, speak with authority, and immediately command credibility with direct reports, the executive team, and external stakeholders.
• You possess exceptional judgment and the ability to synthesize complex information rapidly, turning ambiguity into clear frameworks, options, and recommendations.
• You are comfortable making decisions with incomplete information and navigating highly ambiguous situations while maintaining composure and clarity for the leadership team.
• You demonstrate superior written and verbal communication skills, with the ability to tailor your style for the board, C-suite executives, and operational leaders.
• You have a strong track record of operational excellence, including budget ownership, prioritization, and disciplined execution across multiple concurrent initiatives.
• You are a proactive problem-solver who identifies issues before they escalate and takes ownership of fixing misalignments without requiring explicit direction.
• You have experience working closely with a Chief Operating Officer or equivalent executive partner and understand the demands of supporting a high-visibility, mission-critical leadership role.
• You are highly organized, disciplined, and capable of managing a dynamic workload with competing priorities while maintaining attention to detail and follow-through.
• You are comfortable working within a matrixed organization and influencing peers and stakeholders who do not report to you through clarity of purpose and collaborative problem-solving.