Chief of Staff, CEO

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 Chief of Staff in the San Francisco Bay area to join our Executives team reporting to the Chief Executive Officer. This role is a hybrid role based in the USA.

In this role, you’ll play a key role in amplifying the CEO’s impact and keeping the executive team aligned by owning the executive operating rhythm, driving cross-functional initiatives, and authoring the CEO’s internal and external communications. This is a great opportunity for someone who thrives in a high-visibility, fast-moving, AI-forward environment and enjoys working cross-functionally with teams like the Executive Leadership Team, the Board, Finance, and Marketing. The ideal candidate brings strong skills in executive writing, strategic planning, and AI fluency.

What You'll Do:

CEO Communications (Internal & External)

Develop and deliver high-impact CEO communications including presentations, scripts, talking points, and messaging for internal meetings, industry conferences, customer engagements, and stakeholder interactions.

Prepare the CEO and other executives for public speaking engagements and media appearances. Own pre-prep, vetting, and follow-through on inbound and outbound CEO speaking requests in partnership with Marketing.

Draft company-wide announcements (executive hires, departures, org changes, M&A) and CEO thought leadership in his voice, newsletters, blogs, LinkedIn. Partner with Marketing and PR on press releases, books, and other external media.

Coordinate CEO-driven cultural initiatives, including Childlike Joy videos and other programs.

Executive Team Operations

Set the agenda, drive discussion, and own follow-through for executive team operating meetings, offsites, and deep dives. Ensure clear ownership of decisions and actions.

Organize and facilitate the fiscal year’s key meeting calendar, Board meetings, executive offsites, QBRs, All Hands, Weekly Huddles, ELT, and weekly operations meetings, partnering with the events team and other Chiefs of Staff on logistics, agenda, and follow-up.

Attend strategic meetings, conferences, and offsites with the CEO. Drive prep, capture decisions and timelines, and own follow-through.

Board & Investor Engagement

Own the narrative, content, and coordination for board decks, board letters, and investor materials. Ensure the CEO is fully prepared for high-stakes Board moments.

Support logistics and prep for the CEO’s weekly Board Working Team (BWT) call. Manage Board document distribution in Box and serve as the day-to-day point of contact for the Vista team.

Company-Level Strategy & Annual Planning

Run the full life cycle of the annual strategic planning process (AOP) in partnership with Finance, the CFO, and ELT. Translate strategic priorities into resource and investment decisions for CEO and CFO review.

Own and run the V2MOM process, defining at the ELT level and supporting cascading throughout the rest of the organization. Drive mid-cycle tracking and end-of-cycle reporting.

Provide analytical and project management support on M&A and strategic partnership evaluations as needed.

Project Ownership

Drive high-priority, cross-functional CEO initiatives end-to-end. Define the problem, assemble the working team, manage stakeholder alignment, and monitor progress through to delivery.