Lead Executive Assistant to the CEO

OpenGov•San Francisco, CA

20h•Onsite

About The Position

We are seeking a dynamic and highly trusted Lead Executive Assistant to provide high-level, strategic support to our CEO. This role is mission-critical to the rhythm and effectiveness of our executive team and demands exceptional judgment, foresight, grit, and strong business acumen. As the right hand to the CEO, you will act as an extension of the executive’s leadership style, communication, and priorities. You will manage complex calendaring and travel, drive cross-functional coordination, drive planning of leadership offsites and team events, and lead key administrative and operational processes. You will work in close partnership with the Chief of Staff to the CEO, aligning on priorities, communications, decision making, and planning to maximize executive effectiveness. Moreover, you will be a key contributor toward coordinating with cross-functional executive assistants and Executive Leadership. This is a unique opportunity to play a vital role at the heart of a fast-paced, high-growth SaaS company, supporting a leader who values clarity, trust, discretion, and excellence.

Requirements

Bachelor’s degree preferred.
8+ years of experience as a trusted Executive Assistant supporting C-level executives in high-growth or complex environments (preferably in tech/SaaS).
Demonstrated ability to manage executive operations at scale, exercising seasoned judgment and navigating ambiguity.
Strong project management capability with experience leading and influencing cross-functional initiatives independently.
Proven success influencing across senior levels and handling sensitive, high-stakes situations with discretion and integrity.
Executive-level communication, writing, and presentation skills; comfort navigating high-pressure environments and sensitive information.
High emotional intelligence, professional maturity, and sound judgment.
Technically adept; proficient in Google Workspace, Slack, Zoom, Claude, OpenAI and modern productivity tools.
Strong project management skills; able to anticipate, follow through, and problem-solve independently.

Nice To Haves

Operates with discretion, reliability, and integrity at all times.
Resourceful, proactive, and results-oriented; thrives in a culture of ownership and accountability.
Brings calm and clarity when navigating ambiguity or change.
Meticulous attention to detail and a strong drive to exceed expectations.
A true partner—collaborative, curious, and deeply committed to team success.
Willing and able to work off-hours or weekends as needed to support key initiatives.
A dependable team player who steps in wherever needed to drive impact.

Responsibilities

Manage and optimize the CEO’s complex calendar, aligning time and focus with critical business priorities. Proactively identify and resolve scheduling conflicts, exercising sound judgment and providing recommendations to ensure seamless daily execution.
Own and optimize all travel logistics, including visas, agendas, and itineraries, for both domestic and international travel.
Prepare, synthesize, and review executive-level materials, including board documents, strategic briefings, and confidential communications.
Track and follow up on action items across internal and external stakeholders.
Represent the executive office with clarity, poise, and credibility across internal and external stakeholders.
Partner with the Chief of Staff to drive executive cadence, operational planning, prepare for key meetings, and ensure alignment across functions.
Drive and manage cross-functional coordination among executive assistants, Chiefs of Staff, and department leaders to ensure smooth operating rhythms, aligned decision-making, and effective facilitation of leadership team cadences, quarterly planning cycles, and executive offsites.
Surface and resolve operational gaps through collaboration, influence, and creative problem-solving.
Act as a perceptive advisor by monitoring organizational dynamics and surfacing insights to keep the CEO informed and aligned.
Lead and continuously improve administrative processes, including calendar strategy, travel logistics, expense management, contract workflows, and signature tracking.
Triage and execute high-complexity, cross-functional requests, ensuring clear delegation, executive visibility, and follow-through on critical deliverables.
Continuously evaluate and refine operational infrastructure to ensure it meets the growing complexity and pace of the executive office.
Occasionally manage high-touch personal logistics and ensure they align with professional obligations.
Act as a mentor and escalation point to the broader EA team, helping to elevate the EA function across the company.
Independently organize and manage strategic offsites, key leadership forums, and team events.
Build and maintain strong relationships with internal and external stakeholders to drive alignment and influence outcomes.
Coordinate seamlessly with internal stakeholders to ensure the successful execution of high-profile engagements.