Senior Director, Chief of Staff

Summary

Join Upwork as their Chief of Staff to support the Umami AI/ML team, working directly with the Head of AI and Machine Learning. This high-impact role involves strategic operations, aligning priorities, optimizing workflows, and scaling machine learning innovation. You will manage planning cycles, OKRs, and cross-functional initiatives, ensuring progress is measurable. Building and maintaining systems to track outcomes and report on key milestones are crucial. Leading special projects to accelerate the team's impact and efficiency is also expected. You will represent the AI/ML team in leadership forums and champion a culture of inclusion and transparency. This unique opportunity allows you to shape the future of AI at Upwork and work at the forefront of cutting-edge research.

Requirements

• 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

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

Benefits

• Comprehensive medical coverage for you and your family
• Unlimited PTO
• A 401(k) plan with matching
• 12 weeks of paid parental leave
• An Employee Stock Purchase Plan