Senior Director, Chief of Staff

Location: Schiller Park
Posted on: June 23, 2025

Job Description:

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.

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