Executive Assistant

Gainsight is building the AI-driven future of customer success, from retention to growth. Its AI-powered CustomerOS platform helps more than 2,000 companies drive learning, adoption, community connection, and customer success.

Gainsight is seeking a full-time Executive Assistant to support the CEO and join the Executive Assistant team. Reporting to the Senior Manager, Talent Development, this role will maximize the CEO’s effectiveness by managing day-to-day operations, proactively coordinating priorities, and serving as a trusted partner in a fast-paced, global, and evolving environment.

This is a remote role for someone located in the San Francisco Bay Area, with the expectation of working onsite at the San Francisco location whenever the CEO is present. The role may require occasional travel of up to 30% for leadership meetings, company events, or other business needs.

The starting base salary range is $110,000–$125,000 USD annually. The role is also eligible for an annual bonus and participation in Gainsight’s equity program, along with comprehensive benefits including medical, dental and vision coverage, flexible PTO, a 401(k) plan, remote work options, a fertility stipend, coworking access, and quarterly Recharge Holidays.

• Must be located in the San Francisco Bay Area.
• 10+ years of experience as an Executive Assistant, including 3–5 years of experience directly supporting a CEO, ideally within a fast-paced, global organization.
• Demonstrated ability to operate as a trusted partner to a CEO, with exceptional judgment, discretion, anticipation, and ability to understand and prioritize business needs.
• Expert-level experience managing highly complex executive calendars, including 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-level logistics.
• Strong experience managing executive expenses with exceptional accuracy, organization, and attention to detail.
• Exceptional written and verbal communication skills, with the ability to confidently interact with senior executives, Board members, customers, partners, and teammates at all levels.
• Exceptional follow-through, organization, prioritization, and attention to detail, with a strong sense of urgency and the ability to remain composed when priorities shift.
• Highly professional and polished, with experience handling confidential and sensitive information with discretion.
• Ability to leverage AI and emerging technology to enhance effectiveness, streamline administrative workflows, improve meeting preparation and follow-up, organize information, draft communications, and identify opportunities to save time.
• Nice to have: Experience supporting a CEO within a SaaS, technology, or private equity-backed organization.

• Manage the CEO’s time and priorities, keeping the calendar aligned to the highest-value business priorities and proactively resolving conflicts.
• Own seamless operational execution, including travel, expenses, meetings, logistics, and follow-ups, ensuring they are completed accurately, proactively, and on time.
• Keep the CEO prepared and supported by ensuring the right context, materials, and information are available ahead of key meetings and decisions.
• Build strong, trusted relationships across the Executive Leadership Team, Board, customers, partners, and key internal stakeholders.
• Continuously improve processes, including 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.