Senior Director, Chief of Staff
Location: San Diego
Posted on: June 23, 2025
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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.
Keywords: , Oceanside , Senior Director, Chief of Staff, IT / Software / Systems , San Diego, California
