Chief of Staff

Summary

Join Upwork as their Chief of Staff to the President & CEO and become a strategic partner and force multiplier for the executive office. You will optimize the CEO's time, provide strategic counsel and data-driven insights, serve as a thought partner across the Executive Leadership Team, lead strategic analyses and projects, and run the operational rhythms of the Office of the CEO. Represent the CEO internally and externally, and elevate the effectiveness of the CEO's immediate team. This role requires strategic thinking, analytical skills, experience leading cross-functional initiatives, and the ability to build trust-based relationships with senior stakeholders. The position offers the opportunity to influence company-wide priorities and contribute to the future of work. Upwork provides a remote-first work environment and offers comprehensive benefits.

Requirements

• Demonstrated ability to operate at an executive level with clarity, influence, and discretion, particularly in ambiguous, high-pressure environments
• Sharp strategic thinking and analytical horsepower—able to synthesize complexity, uncover insights, and drive to clarity
• Proven experience leading initiatives across functions with minimal structure, and bringing others along through influence rather than authority
• Willingness to operate across altitudes, from high-level strategy to fine-grain operational detail, with humility and stamina
• A track record of building trust-based relationships with senior stakeholders and leading with a customer- and company-first mindset

Responsibilities

• Optimize the CEO’s time and impact by streamlining planning cadences, meeting structures, and material preparation, ensuring executive engagement is always high-leverage
• Provide strategic counsel and data-driven insights to the CEO on emergent issues, organizational dynamics, and company-wide initiatives
• Serve as a thought partner and connector across the Executive Leadership Team (ELT), fostering alignment and surfacing opportunities, risks, and trade-offs
• Lead and drive unowned strategic analyses and projects that span multiple functions or lack a clear home, delivering insights that shape high-stakes decisions
• Run the operational rhythms of the Office of the CEO, including ELT meetings, Board interface, planning cycles, and cross-functional cadences
• Represent the CEO in key internal and external interactions, ensuring alignment with Upwork’s strategic priorities and culture
• Elevate the effectiveness of the CEO’s immediate team by offering strategic guidance, refining outputs, and enhancing cross-functional collaboration

Benefits

• Comprehensive medical coverage for you and your family
• Unlimited PTO
• A 401(k) plan with matching
• 12 weeks of paid parental leave
• An Employee Stock Purchase Plan