About this role.
This senior Chief of Staff role partners directly with Upwork’s COO and GM of Marketplace to translate strategy into execution across a broad portfolio of business functions. The position owns operating rhythms, executive and board preparation, planning processes, decision support, and cross-functional issue resolution. It requires more than 10 years of relevant experience, strong business judgment, discretion, executive presence, and exceptional written communication. The successful candidate will influence senior leaders without formal authority while maintaining clarity, accountability, and continuity during high-velocity operations and organizational change.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I would begin by clarifying the organization’s strategic priorities, decision rights, critical metrics, and recurring forums. I would then design a lightweight cadence of business reviews, leadership meetings, and planning checkpoints that focuses on decisions, risks, owners, and follow-through rather than status reporting. I would regularly refine the process based on where commitments or information are breaking down.
I would identify the decision required, gather the relevant data and stakeholder perspectives, and distinguish facts from assumptions or contested points. The briefing would present a concise recommendation, credible alternatives, trade-offs, risks, and clear proposed next steps. I would also prepare the COO for likely questions and ensure the supporting materials are accurate, appropriately sequenced, and aligned with the executive narrative.
I build credibility by being prepared, objective, and reliable, while grounding discussions in shared business outcomes. I seek to understand each leader’s constraints and incentives, make decision rights explicit, and present practical options instead of merely surfacing problems. When needed, I respectfully escalate with a clear statement of the impact of inaction and the decision required.
I look for repeated handoff failures, duplicated work, unclear ownership, inconsistent metrics, and decisions that are repeatedly revisited. I map the workflow and stakeholders, isolate the root cause, then convene the minimum necessary group to clarify accountability, dependencies, and deadlines. I track the agreed resolution until the new operating behavior is established.
I would treat confidential discussions as privileged and be direct with the COO about risks, dissenting views, and my recommendations. Once a decision is made, I would communicate it consistently and constructively, providing the context others need to execute without disclosing sensitive deliberations. Trust comes from maintaining that distinction consistently, especially in difficult situations.
Upwork Inc.’s (Nasdaq: UPWK) family of companies connects businesses with global, AI-enabled talent across every contingent work type including freelance, fractional, and payrolled. This portfolio includes the Upwork Marketplace, which connects businesses with on-demand access to highly skilled talent across the globe, and Lifted, which provides a purpose-built solution for enterprise organizations to source, contract, manage, and pay talent across the full spectrum of contingent work. From Fortune 100 enterprises to entrepreneurs, businesses rely on Upwork Inc. to find and hire expert talent, leverage AI-powered work solutions, and drive business transformation. With access to professionals spanning more than 10,000 skills across AI & machine learning, software development, sales & marketing, customer support, finance & accounting, and more, the Upwork family of companies enables businesses of all sizes to scale, innovate, and transform their workforces for the age of AI and beyond.
Since its founding, Upwork Inc. has facilitated more than $30 billion in total transactions and services as it fulfills its purpose to create opportunity in every era of work. Learn more about the Upwork Marketplace at Upwork.com and follow us on LinkedIn, Facebook, Instagram, TikTok, and X; and learn more about Lifted at Go-Lifted and follow on LinkedIn.
About the Role
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.
What You’ll Do
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 You Bring
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.
Come change how the world works.
At Upwork, you’ll shape the future of work for a global, remote-first workforce, creating economic opportunities for professionals worldwide. 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. Visit our Life at Upwork page to learn more about our values, working principles, and the overall employee experience.
Ready to help shape the future of work? Check out our Careers page and follow us on LinkedIn, Facebook, Instagram, TikTok, and X to learn more about life at Upwork.
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.
The annual base salary range for this position is displayed below. The range displayed reflects the minimum and maximum salary for this position, and individual base pay will depend on your skills, qualifications, experience, and location. Additionally, this position is eligible for the annual bonus plan or sales incentive plan and eligibility to participate in our long term equity incentive program.
Annual Base Compensation
$229,000—$384,000 USD
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
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