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Chief of Staff to the President & CEO

Palo Alto, California, United States

Chief of Staff to Upwork President & CEO

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.

This is an in-person role based out of our Palo Alto, CA Headquarter. 

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.

What it takes to catch our eye

  • 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.

Come change how the world works.

At Upwork, you’ll shape the future of work for a global, remote-first workforce, creating economic opportunities for professionals worldwide. While we have a physical office in Palo Alto, we currently hire full-time employees in 21 U.S. states, making it easier than ever to join our mission from wherever you call home.

Our culture is built on trust, risk-taking, customer focus, and excellence, all in service of our core mission: to create economic opportunities so people have better lives. We embrace authenticity and inclusion, encouraging everyone to bring their whole selves to work. Personal and professional growth is a priority here, supported through development programs, mentorship, and our Upwork Belonging Communities.

We’re proud to offer benefits that go beyond the basics, including comprehensive medical coverage for you and your family, unlimited PTO, a 401(k) plan with matching, 12 weeks of paid parental leave, and an Employee Stock Purchase Plan. Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.

Ready to help shape the future of work? Check out our Careers page and follow us on LinkedIn, Facebook, Instagram, TikTok, and X. to learn more about life at Upwork.

Upwork is an Equal Opportunity Employer committed to recruiting and retaining a diverse and inclusive workforce. We do not discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, or other legally protected characteristics under federal, state, or local law.

Please note that a criminal background check may be required once a conditional job offer is made. Qualified applicants with arrest or conviction records will be considered in accordance with applicable law, including the California Fair Chance Act and local Fair Chance ordinances.

 

The annual base salary range for this position  is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.

Annual Base Compensation

$254,750 - $402,750 USD

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