Executive Assistant

We’re building the AI-driven future of customer success, from retention to growth!

We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link.

About This Role:

We're looking for a full-time Executive Assistant in the San Francisco Bay area to join our Executive Assistant team. You'll report to the Senior Manager, Talent Development.
In this role, you’ll play a key role in maximizing the effectiveness and impact of Gainsight’s CEO by ensuring seamless day-to-day operations, proactively managing priorities, and serving as a trusted partner. You’ll anticipate needs, navigate competing priorities, and create the structure that allows the CEO to remain focused on Gainsight’s highest-impact business initiatives. This is a great opportunity for someone who thrives in a fast-paced, global, and constantly evolving environment and enjoys working cross-functionally. The ideal candidate brings exceptional skills in executive partnership, complex calendar and travel management, prioritization, and operational execution. This role is remote with the expectation that you will be on-site at our San Francisco location whenever the CEO is present. However, there is flexibility to work from home when they are traveling or out of the office.

What You'll Do:

• 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 — travel, expenses, meetings, logistics, and follow-ups completed accurately, proactively, and on time.

• Keep the CEO prepared and supported, ensuring the right context, materials, and information are in hand 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.

This role may require occasional travel (up to 30%) for leadership meetings, company events, or other business needs. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the CEO and business.

What We're Looking For:

• Must be located in the 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 the 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 demonstrated experience handling confidential and sensitive information with discretion.

• Leverages AI and emerging technology to enhance day-to-day effectiveness, streamline administrative workflows, improve meeting preparation and follow-up, organize information, draft communications, and identify opportunities to save time and operate more efficiently.

Nice-to-have skills or experience:

• Experience supporting a CEO within a SaaS, technology, or private equity-backed organization.

Why You’ll Love It Here:

Gainsight is a place where innovation is shaped through collaboration, curiosity, and a shared focus on solving real-world problems. With a growing suite of products across customer success, product experience, community, education, and AI-powered relationship intelligence, we continue to evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few:

Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported.

• The starting base salary range for this role is $110,000– $125,000 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. In addition to base pay, this role is eligible for an annual bonus and participation in Gainsight’s equity program.

• We offer a comprehensive benefits package including fully covered medical premiums (employee-only), flexible PTO, 401(k) plan, dental and vision coverage, and remote work options. Additional benefits include a $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset.

Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First. Learn more here.

Our Growth Opportunities: From mentoring to career development opportunities, we’re passionate about helping our teammates learn, grow, and thrive.

Our Parody Videos: No explanation needed. Just watch them here!

If this sounds like the right role for you, we’d love to hear from you.

Additional Information:

We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates.

If you require accommodations or have questions about how your personal data will be used during the hiring process, please contact [email protected].

If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.