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Sr Director, Chief of Staff

Remote

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 strategic, technically fluent Chief of Staff to serve as a force multiplier to our Head of AI/ML and SVP of Engineering. This high-impact role acts as the connective tissue across Engineering, Platform Infrastructure, and AI/ML—turning vision into action and accelerating the execution of our most critical technical priorities.

You’ll lead cross-functional alignment, orchestrate operational excellence, and bring clarity and momentum to complex, high-priority initiatives. As a trusted partner to senior executives, you’ll help shape Upwork’s technical strategy, integrate AI/ML thinking into our broader business, and scale systems that foster velocity, inclusion, and innovation across a growing organization.

Responsibilities

  • Lead execution of company-critical initiatives across Engineering, AI/ML, and Infrastructure—bringing structure, accountability, and forward momentum to cross-functional programs.

  • Translate leadership vision into detailed execution plans, aligning stakeholders and ensuring delivery against defined outcomes.

  • Architect and evolve operating rhythms that optimize communication, decision-making, and transparency across highly technical teams.

  • Build and maintain dashboards, tracking systems, and reporting frameworks that improve visibility into progress and remove organizational friction.

  • Act as a strategic thought partner, helping shape technical priorities and ensuring engineering, infrastructure, and AI/ML strategies align with business goals.

  • Identify talent gaps, process inefficiencies, and organizational misalignments; drive solutions that foster high performance and inclusive culture.

  • Lead executive communications and org-wide messaging, ensuring clarity, consistency, and alignment across teams and levels.

What it takes to catch our eye

  • 10+ years of experience in strategic operations, Chief of Staff, or technical program leadership roles, preferably within AI/ML, engineering, or infrastructure domains.

  • Proven track record of driving strategic, complex programs at scale across cross-functional teams in high-growth environments.

  • Deep understanding of how technical R&D organizations operate—including ML lifecycle, platform architecture, and product collaboration.

  • Executive presence with the ability to influence at all levels and foster alignment in ambiguous, rapidly evolving contexts.

  • Systems thinker with a bias for action, strong emotional intelligence, and a low-ego, high-candor communication style.

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

$229,000 - $275,000 USD

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