Executive Assistant, Office of the CEO

Upwork•Palo Alto, CA

2d•$116,750 - $166,250•Onsite

About The Position

Upwork Inc. is seeking a proactive, highly organized Executive Assistant to support the Office of the CEO. This in-person role, based in Palo Alto, involves close collaboration with the Executive Assistant to the CEO, Chief of Staff to the CEO, and the CEO to ensure seamless day-to-day operations, thoughtful coordination, and exceptional execution. This position offers the opportunity to work at the center of Upwork's leadership team, where anticipating needs, navigating shifting priorities, and solving problems independently will be crucial. The role serves as a trusted partner, managing complex logistics, supporting executive workflows, and creating an exceptional experience for internal and external stakeholders. Success requires ultimate discretion, sound judgment, attention to detail, and a collaborative mindset. The Executive Assistant will have the autonomy to own key operational responsibilities, identify process improvement opportunities, and contribute to the effective operation of the Office of the CEO.

Requirements

Proven experience as an Executive Assistant, with demonstrated success providing executive-level support, including complex calendar management, travel coordination, meeting logistics, and managing multiple priorities with minimal day-to-day direction.
Ability to anticipate needs, independently troubleshoot and resolve operational challenges, maintain exceptional attention to detail, and follow up in a timely way.
Ability to handle sensitive or confidential information with discretion and professionalism.
Demonstrated ability to balance workload under short deadlines, pivot to changing priorities, and respond calmly and proactively under pressure.
Excellent written and verbal communication skills, with the ability to build an atmosphere of trust and collaboration.
Comfortable interacting at all levels of the organization.
Experience with Google Workspace (Calendar, Gmail, Docs, Sheets), Slack, and productivity tools.
Practical experience using AI to improve workflows, draft communications, or organize information.
Ability to evaluate AI-generated outputs for accuracy and protect confidential information.
Ability to work on-site in Palo Alto to provide hands-on executive support.
Willingness to be available outside standard business hours.

Responsibilities

Provide in-office support to the Office of the CEO (CEO, Chief of Staff and EA to CEO) through extensive calendar management, including multi-channeled work streams.
Partner with the CoS and EA to manage CEO and CoS calendars and implement the executive team's operating model.
Own day-to-day in-office operations for the Office of the CEO, including meeting preparation, daily lunches, catering, refreshments, support executive visits and guests, and other hospitality needs to create a welcoming, well-organized environment.
Coordinate executive travel and logistics in partnership with the EA to the CEO, including domestic and international itineraries, aviation, ground transportation, accommodations, and real-time adjustments.
Plan and execute executive meetings, leadership offsites, and special events, managing scheduling, venues, vendors, materials, and logistics.
Support the CoS and EA to the CEO in tracking timelines, coordinating cross-functional stakeholders, and following up to keep time-sensitive work on track.
Source and manage venues and vendors, partnering with cross-functional teams to facilitate contract renewals and onboard new vendors.
Manage administrative and operational workflows, including expense reporting, invoice processing, calendar analysis, and contract tracking.
Collaborate across teams to improve execution and efficiency, proactively identifying operational gaps, streamlining processes, and leveraging approved AI and productivity tools.
Act as a visible leader and culture carrier within the admin team at Upwork, connecting with admin partners across locations, sharing best practices, and modeling collaboration and care.
Build trusted relationships and safeguard confidential information, partnering with executive stakeholders, administrative partners, and both internal and external contacts, while exercising discretion, sound judgment, and responsiveness to time-sensitive needs.