Sr Director, Chief of Staff

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.

We’re looking for a Chief of Staff to support our Umami AI/ML team, working directly with Andrew Rabinovich, Upwork’s Head of AI and Machine Learning. In this high-impact role, you will serve as a strategic operator, thought partner, and organizational force multiplier—aligning priorities, optimizing cross-functional workflows, and amplifying our ability to scale machine learning innovation. This is a unique opportunity to help shape the future of AI at Upwork and work at the forefront of cutting-edge research and real-world impact.

Responsibilities

• Drive strategic alignment and operational execution across the Umami AI/ML team by coordinating workstreams and ensuring consistent communication across key stakeholders.

• Partner with the Head of AI and Machine Learning to manage planning cycles, OKRs, and cross-functional initiatives—ensuring priorities are clear and progress is measurable.

• Build and maintain systems to track outcomes, report on key milestones, and surface insights that support data-driven decision-making across R&D efforts.

• Lead and deliver special projects that accelerate the impact and efficiency of the AI/ML team—from process optimization to resourcing strategies.

• Create clarity across ambiguity by proactively identifying gaps, proposing solutions, and facilitating decision-making across research, engineering, and product teams.

• Represent the AI/ML team in leadership forums and cross-functional partnerships, translating vision into action and ensuring consistent visibility of progress and challenges.

• Champion a culture of inclusion, transparency, and shared learning across a highly technical, interdisciplinary team.
   

What it takes to catch our eye

• 10+ years of relevant experience in strategic operations, business planning, or Chief of Staff-type roles—ideally within R&D, AI/ML, or innovation-led teams.

• Strong understanding of how technical R&D teams operate—especially within AI, machine learning, or similar scientific domains.

• Proven ability to manage and influence across teams, aligning multiple stakeholders and balancing competing priorities.

• Track record of designing and implementing systems that enable scale, transparency, and continuous improvement.

• Comfortable navigating ambiguity and complexity with clarity, empathy, and a bias toward action.
   

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.