Senior Director, Chief of Staff Position Available In Montgomery, Pennsylvania

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 trustUpwork’s platform to access expert talent, leverage AI-powered worksolutions, and drive meaningful business outcomes. Upwork’sAI-powered platform has facilitated over $20 billion in economicopportunity for professionals worldwide. With professionalsspanning 10,000 skills, including AI and machine learning, softwaredevelopment, sales and marketing, customer support, finance andaccounting, and more, Upwork empowers businesses of all sizes toscale, innovate, and build agile teams. We’re looking for a Chiefof Staff to support our Umami AI/ML team, working directly withAndrew Rabinovich, Upwork’s Head of AI and Machine Learning. Inthis high-impact role, you will serve as a strategic operator,thought partner, and organizational force multiplier—aligningpriorities, optimizing cross-functional workflows, and amplifyingour ability to scale machine learning innovation. This is a uniqueopportunity to help shape the future of AI at Upwork and work atthe forefront of cutting-edge research and real-world impact.

Responsibilities

• Drive strategic alignment and operationalexecution across the Umami AI/ML team by coordinating workstreamsand ensuring consistent communication across key stakeholders.
• Partner with the Head of AI and Machine Learning to manage planningcycles, OKRs, and cross-functional initiatives—ensuring prioritiesare clear and progress is measurable.
• Build and maintain systemsto track outcomes, report on key milestones, and surface insightsthat support data-driven decision-making across R D efforts.
• Lead and deliver special projects that accelerate the impact andefficiency of the AI/ML team—from process optimization toresourcing strategies.
• Create clarity across ambiguity byproactively identifying gaps, proposing solutions, and facilitatingdecision-making across research, engineering, and product teams.
• Represent the AI/ML team in leadership forums and cross-functionalpartnerships, translating vision into action and ensuringconsistent visibility of progress and challenges.
• Champion aculture of inclusion, transparency, and shared learning across ahighly technical, interdisciplinary team. What it takes to catchour eye
• 10 years of relevant experience in strategic operations,business planning, or Chief of Staff-type roles—ideally withinR D, AI/ML, or innovation-led teams.
• Strong understanding ofhow technical R D teams operate—especially within AI, machinelearning, or similar scientific domains.
• Proven ability to manageand influence across teams, aligning multiple stakeholders andbalancing competing priorities.
• Track record of designing andimplementing systems that enable scale, transparency, andcontinuous improvement.
• Comfortable navigating ambiguity andcomplexity with clarity, empathy, and a bias toward action.