Regional Operations Director Jobs in Palo Alto, CA

INTRODUCTION

Upwork's COO and GM of Marketplace operates across one of the broadest organizational portfolios in the company - spanning Legal, Information Security, Marketing, Payments, Trust & Safety, Communications, Customer Support, Design, and Product. The Chief of Staff to the COO exists to make that model work: not as a coordinator, but as a true operating partner who extends the COO's capacity, sharpens decision-making, and holds together a complex, fast-moving organization. This role requires someone who has earned the confidence to walk into any room, speak with authority, and immediately earn credibility - with the COO's direct reports, with the executive team, and with external stakeholders. It is a senior, strategic seat, and will be treated as one.

Responsibilities:

Strategic Partnership:

- Serve as a trusted thought partner - not as a gatekeeper, but as someone who makes every interaction with the COO more valuable. You will be the person the COO thinks out loud with, who surfaces risks before they become problems, and who ensures decisions are grounded in the right data and framing. You will push back privately, represent the COO's point of view publicly, and discern between the two like it was remembering to breathe.
- Prepare the COO for high-stakes conversations - drafting and driving board presentations, executive reviews, cross-functional negotiations - surfacing not just what is known, but what remains ambiguous or contested. Where there's a decision to be made, you'll come with options and a point of view, not just a summary.

Operational Integration:

- Own the operating rhythm of the COO organization. Monthly and quarterly business reviews, annual planning cycles, leadership forums - you will ensure these are substantive, efficient, and connected to strategic priorities rather than calendar obligations. You'll work directly with finance and functional leads to ensure budget is managed with discipline and that trade-off decisions are made proactively, not reactively.
- Across a portfolio this wide, fragmentation is the enemy. You will identify where alignment is breaking down, where decisions are falling through the cracks, and where accountability needs to be reinforced - and you will fix those things without waiting to be asked.

Execution and Clarity:

- Maintain a clear line of sight across key initiatives and ensure the COO has the information, context, and preparation needed to drive outcomes - not just attend meetings. You will own the quality of materials that come to the COO, provide direct feedback to senior leaders preparing those materials, and ensure that executive time is protected for the work that only the COO can do.
- When cross-functional friction stalls something important, you will unblock it. You will know when to convene the right people, when to clarify decision rights, and when to escalate versus resolve.

Culture and Continuity:

- Model the leadership values Upwork expects of its people. Be the connective tissue between strategy and execution - translating intent into direction for a team that operates across remarkably diverse functions. During transitions or periods of organizational change, be the source of stability and continuity.

WHAT IT TAKES TO CATCH OUR EYE:

- You have operated at the intersection of strategy and execution in a high-velocity environment - consulting, investment banking, a high-growth tech company, or some combination. You understand how businesses work, how organizations behave under pressure, and how to move complex stakeholders without formal authority.
- You are organized in a way that others notice. Not in a process-for-process's-sake way, but in a way that instills confidence: things don't fall through the cracks around you, and the people you work with know it. You think clearly under ambiguity, write and communicate with precision, and can build a compelling deck and the strategy behind it in the same sitting.
- You have the discretion and judgement to be a confidant - discreet with sensitive information, frank in private, and diplomatically effective in every other setting. You know when to be direct and when to be patient. You don't need credit, but you do need to be trusted, and you earn that trust by consistently being great at your job and consistently acting with integrity.
- 10+ years of relevant experience; MBA or equivalent strongly preferred. Prior Chief of Staff experience or a similar senior operating role is a plus, but the profile matters more than the title.

COMPENSATION

While we have a physical office in Palo Alto, we currently hire full-time employees in 34 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.

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 Company is committed to conducting an individualized assessment and giving all individuals a fair opportunity to provide relevant information or context before making any final employment decision. We use BrightHire, an AI-enabled tool, to record interviews and summarize interview transcripts. The tool allows the interviewer to focus on the discussion and does not score or evaluate candidates or make recommendations. The interview transcripts are reviewed, and decisions are only made by humans. Candidates who prefer not to have their interview recorded through BrightHire can opt out when the interview is scheduled. To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice.