Chief of Staff, CEO

Gainsight; United States; Remote; USD 150,000 - 230,000; Full time

Job summary

Gainsight is seeking a full-time Chief of Staff to join the Executives team, reporting to the CEO. This remote role is based in the USA.

You will amplify the CEO’s impact by owning the executive operating rhythm, driving cross-functional initiatives, and authoring communications for internal and external audiences. You’ll work with the ELT, Board, Finance, and Marketing; bring strong skills in executive writing, strategic planning, and AI fluency; own strategic planning, data dashboards, and

Qualifications

• 5–10 years of related experience and a Bachelor's degree (or equivalent experience).
• Experience crafting executive-level communications for internal and external audiences.
• Proven ability to drive cross-functional initiatives and align leadership teams.

Responsibilities

• Develop and deliver high-impact CEO communications including presentations, scripts, talking points, and messaging for internal meetings, conferences, and stakeholder interactions.
• Own preparation for public speaking engagements and media appearances, coordinating with Marketing.
• Lead executive team operating rhythm, calendar, meetings, and decisions with clear ownership and follow-through.
• Own board decks, investor materials, and prep for Board moments; coordinate with Vista and Board teams.
• Run annual strategic planning (AOP) with Finance and ELT, translating priorities into resource decisions.
• Drive cross-functional CEO initiatives end-to-end and embed AI into workflows for faster planning and reporting.
• Be hyper-responsive across channels and travel as needed to support the CEO.

Skills

Executive communication

Strategic planning

AI fluency

Cross-functional collaboration

Project management

Education

Bachelor's degree or equivalent experience

Tools

Box

Job description

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 to join our Executives team reporting to the Chief Executive Officer. This role is a remote 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.

Build and maintain the data layer for executive decision-making, performance dashboards, KPI tracking, and business reviews that synthesize cross-functional and BU-level data for the ELT. Embed AI into these workflows to make planning, reporting, and analysis faster and higher quality.

Serve as a shared strategic resource to BU GMs and functional leaders, providing executive visibility on issues that span organizational boundaries.

Hyper-Responsiveness and Flexibility

Be hyper-responsive across email, Slack, text, and phone, including outside of normal business hours and Sunday evenings to prepare for the business week.

Travel locally, domestically, and internationally to be onsite with the CEO as needed.

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:

5-10 years of related experience and a Bachelor's degree (or equivalent experience), with a proven track record i