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 to join our Sales Operations team reporting to the Senior Manager, Talent Development. This role is a remote role based in Mexico.

In this role, you'll play a key role in keeping Gainsight's senior leaders operating at full capacity by proactively managing complex calendars, coordinating multi-leg global travel, and ensuring expenses stay accurate and on time. This is a great opportunity for someone who thrives in a fast-paced, high-velocity environment and enjoys working cross-functionally with teams like fellow Executive Assistants and executives' extended teams. The ideal candidate brings strong skills in high-volume global calendar management, complex international travel coordination, and discreet handling of confidential information.

What You'll Do:

• Proactively manage executive calendars anticipating scheduling conflicts, prioritizing competing demands, and maintaining awareness of executive priorities without being prompted.

• Support up to 3 Senior leaders simultaneously, with occasional task-switching to cover other EAs (e.g., maternity leave coverage), working with flexible executive schedules rather than fixed hours.

• Coordinate logistics for meetings, ensuring all necessary materials, agendas, and resources are prepared well in advance.

• Manage complex, multi-leg global travel arrangements including US and UK trips ensuring seamless itineraries and responding quickly to last-minute changes.

• Track and submit expense reports accurately and on time, including familiarity with tools such as Concur.

• Build strong, trust-based relationships with the executive's extended team and key stakeholders.

• Handle confidential information with discretion and maintain a high level of professionalism at all times.

• Leverage AI tools and modern productivity software to operate efficiently and stay ahead of the pace.

• Take on light personal tasks to support the executives' overall workflow as needed.

• Other duties as assigned.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. This role will require occasional travel for team meetings, training, or company events.

What We're Looking For:

• 6+ years as an Executive Assistant supporting C-level executives — not just VP or director-level.

• 6+ years of high-volume global calendar management across multiple time zones, with a track record of proactive, not reactive, scheduling.

• 6+ years coordinating complex international travel (multi-leg, multi-country itineraries).

• Demonstrated ability to support multiple executives simultaneously (the pace of supporting 4–5 executives at once is the equivalent of one C-level).

• 3+ years of G Suite experience (Google Calendar, Gmail, Drive); proficiency in expense tools such as Concur.

• Stable employment history with demonstrated tenure in prior roles.

• Comfortable working flexible hours to align with executive time zones and availability.

• Fluent in English; strong written and verbal communication skills.

Preferred skills or experience:

• Background in a fast-paced SaaS or startup tech environment — industry experience is a plus, not a requirement.

• Experience supporting executives across US and UK time zones.

• AI literacy — comfortable using AI tools to improve efficiency and output quality.

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 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’re applying for a role through an Employer of Record (EOR) or contractor arrangement, please note that employment terms and benefits are managed by the EOR or may not apply to non-EOR contractors.