Chief of Staff to the President & CEO at Upwork

Palo Alto, California, United States

Apply Now

Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, MarketplaceIndustries

Requirements

Demonstrated ability to operate at an executive level with clarity, influence, and discretion, particularly in ambiguous, high-pressure environments
Sharp strategic thinking and analytical horsepower—able to synthesize complexity, uncover insights, and drive to clarity
Proven experience leading initiatives across functions with minimal structure, and bringing others along through influence rather than authority
Willingness to operate across altitudes, from high-level strategy to fine-grain operational detail, with humility and stamina
A track record of building trust-based relationships with senior stakeholders and leading with a customer- and company-first mindset

Responsibilities

Optimize the CEO’s time and impact by streamlining planning cadences, meeting structures, and material preparation, ensuring executive engagement is always high-leverage
Provide strategic counsel and data-driven insights to the CEO on emergent issues, organizational dynamics, and company-wide initiatives
Serve as a thought partner and connector across the Executive Leadership Team (ELT), fostering alignment and surfacing opportunities, risks, and trade-offs
Lead and drive unowned strategic analyses and projects that span multiple functions or lack a clear home, delivering insights that shape high-stakes decisions
Run the operational rhythms of the Office of the CEO, including ELT meetings, Board interface, planning cycles, and cross-functional cadences
Represent the CEO in key internal and external interactions, ensuring alignment with Upwork’s strategic priorities and culture
Elevate the effectiveness of the CEO’s immediate team by offering strategic guidance, refining outputs, and enhancing cross-functional collaboration

Skills

Key technologies and capabilities for this role

Strategic PlanningExecutive CommunicationData AnalysisProject ManagementLeadership AlignmentRisk Assessment

Questions & Answers

Common questions about this position

What is the salary for the Chief of Staff role?

This information is not specified in the job description.

Is this Chief of Staff position remote or office-based?

This information is not specified in the job description.

What skills are required for the Chief of Staff to the President & CEO?

Key skills include operating at an executive level with clarity, influence, and discretion in ambiguous environments; sharp strategic thinking and analytical abilities to synthesize complexity; and proven experience leading cross-functional initiatives through influence rather than authority.

What is the team structure for this role at Upwork?

The role works closely with the CEO's immediate team and serves as a thought partner and connector across the Executive Leadership Team (ELT), running operational rhythms including ELT meetings and Board interface.

What makes a strong candidate for the Chief of Staff position?

Strong candidates demonstrate executive-level operation with clarity, influence, and discretion in high-pressure settings, sharp strategic and analytical thinking to drive clarity from complexity, and experience leading cross-functional initiatives through influence.

Upwork

Online platform connecting freelancers and clients

About Upwork

Upwork connects freelancers with clients looking for various services in the gig economy, which focuses on short-term contracts instead of permanent jobs. The platform allows freelancers to create profiles that showcase their skills, while clients can post job listings for specific projects. Freelancers bid on these projects, and clients choose the best candidates based on proposals and reviews. Upwork earns revenue through service fees charged to freelancers based on their earnings, with a tiered structure that rewards long-term client relationships. The platform also offers premium memberships and additional services for enhanced visibility and access to job listings. Upwork provides tools for time tracking, invoicing, and project management, making it easier for both freelancers and clients to manage their work and payments. The goal of Upwork is to facilitate successful project completion by bridging the gap between freelancers and clients.

San Francisco, CaliforniaHeadquarters

2015Year Founded

$143.8MTotal Funding

IPOCompany Stage

Consulting, Enterprise SoftwareIndustries

10,001+Employees

Benefits

Health Insurance

Unlimited Paid Time Off

401(k) Retirement Plan

401(k) Company Match

Parental Leave

Employee Stock Purchase Plan

Risks

Increased competition from Fiverr and Toptal threatens Upwork's market share.

The new Fiverr-style Project Catalog may commoditize services, reducing freelancers' perceived value.

Strategic shifts under new management may not align with current client expectations.

Differentiation

Upwork connects freelancers with clients across diverse industries, enhancing global work opportunities.

The platform offers tools like time tracking and invoicing for efficient project management.

Upwork's tiered fee structure incentivizes long-term client relationships, differentiating it from competitors.

Upsides

Upwork's acquisition of Objective AI enhances its AI capabilities for better talent matching.

The introduction of Featured Jobs increases visibility for job posts, attracting more candidates.

Upwork's recognition as the top job posting site boosts its credibility among employers.

Land your dream remote job 3x faster with AI

Try Jobo Free