Executive Assistant

Gainsight is an AI-powered customer retention platform trusted by more than 2,000 companies. Its CustomerOS platform supports the customer journey from onboarding to outcomes and advocacy.

Gainsight is seeking a full-time Executive Assistant to support its CEO. The role reports to the Senior Manager, Talent Development and is remote, with an expectation of working on-site at the San Francisco location whenever the CEO is present. There is flexibility to work from home when the CEO is traveling or out of the office.

The starting base salary is $110,000–$125,000 USD annually. The role is also eligible for an annual bonus and equity participation. Benefits include medical, dental, and vision coverage, flexible PTO, a 401(k) plan, remote work options, and additional wellness and family benefits.

• Must be located in the San Francisco Bay Area.
• 10+ years of experience as an Executive Assistant, including 3–5 years directly supporting a CEO, ideally in a fast-paced, global organization.
• Ability to act as a trusted CEO partner, demonstrating exceptional judgment, discretion, anticipation, and business prioritization.
• Expertise managing highly complex executive calendars across multiple time zones, shifting priorities, and high-volume internal and external engagements.
• Extensive experience coordinating complex domestic and international travel, including last-minute changes, visas, detailed itineraries, and executive logistics.
• Strong experience managing executive expenses with accuracy, organization, and attention to detail.
• Exceptional written and verbal communication skills and confidence interacting with senior executives, Board members, customers, partners, and teammates at all levels.
• Exceptional follow-through, organization, prioritization, and attention to detail; a strong sense of urgency and the ability to remain composed when priorities shift.
• Professionalism and experience handling confidential and sensitive information with discretion.
• Ability to leverage AI and emerging technology to streamline administrative workflows, improve meeting preparation and follow-up, organize information, draft communications, and improve efficiency.
• Nice to have: Experience supporting a CEO in a SaaS, technology, or private equity-backed organization.

• Manage the CEO’s time and priorities, align the calendar with high-value business priorities, and proactively resolve conflicts.
• Own operational execution for travel, expenses, meetings, logistics, and follow-ups, completing work accurately, proactively, and on time.
• Prepare the CEO for meetings and decisions by ensuring the right context, materials, and information are available in advance.
• Build trusted relationships across the Executive Leadership Team, Board, customers, partners, and key internal stakeholders.
• Continuously improve processes, including through thoughtful use of AI and technology to reduce administrative burden and boost productivity.
• Travel occasionally, up to 30%, for leadership meetings, company events, or other business needs.