Chief of Staff to the President & CEO

Upwork • Palo Alto, CA

194d • $254,750 - $402,750

About The Position

Upwork ($UPWK) is the world’s largest work marketplace, connecting businesses with highly skilled professionals worldwide. From entrepreneurs to Fortune 100 enterprises, companies trust Upwork’s platform to access expert talent, leverage AI-powered work solutions, and drive meaningful business outcomes. Upwork’s AI-powered platform has facilitated over $20 billion in economic opportunity for professionals worldwide. With professionals spanning 10,000+ skills, including AI and machine learning, software development, sales and marketing, customer support, finance and accounting, and more, Upwork empowers businesses of all sizes to scale, innovate, and build agile teams. As Chief of Staff to the President & CEO, you will serve as a strategic partner, integrator, and force multiplier for the executive office. Operating at the highest levels of the organization, you’ll ensure CEO time is focused on the highest-impact activities, amplify executive effectiveness, and lead mission-critical initiatives across the company. This role is both strategic and operationally hands-on, serving as a key ambassador for the CEO internally and externally, and a trusted advisor to the Executive Leadership Team. This is an extraordinary opportunity to influence company-wide priorities, connect executive vision to execution, and contribute meaningfully to the future of work.

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
• 401(k) plan with matching
• 12 weeks of paid parental leave
• Employee Stock Purchase Plan

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 501-1,000 employees