Chief of Staff, CEO

Gainsight • Sacramento, CA

4d • Hybrid

About The Position

Gainsight is seeking a full-time Chief of Staff to the CEO, based in the San Francisco Bay Area in a hybrid role. Reporting to the Chief Executive Officer, this position amplifies the CEO’s impact and keeps the executive team aligned by managing the executive operating rhythm, driving cross-functional initiatives, and developing the CEO’s internal and external communications. The role works closely with the Executive Leadership Team, Board, Finance, Marketing, and other stakeholders in a high-visibility, fast-moving, AI-forward environment.

The Chief of Staff leads CEO communications, executive team operations, Board and investor engagement, annual strategic planning, and priority projects. The role also builds executive decision-making resources such as performance dashboards and KPI tracking, and embeds AI into planning, reporting, and analysis workflows. It requires responsiveness outside normal business hours, including Sunday evenings, and local, domestic, and international travel as needed to accompany the CEO. Responsibilities may evolve with the needs of the team and business, and occasional travel for team meetings, training, or company events is required.

Requirements

• 5–10 years of related experience and a Bachelor’s degree or equivalent experience.
• A proven track record in a Chief of Staff, strategy, business operations, management consulting, investment banking, venture capital, or private equity role.
• Exceptional written communication and demonstrated experience writing in a senior executive’s voice across formats such as Board materials, All Hands narratives, internal announcements, LinkedIn and thought leadership, and customer-facing keynotes.
• Strong structured thinking and the ability to synthesize ambiguous information into clear recommendations and executive-ready materials.
• Ability to manage multiple complex cross-functional workstreams concurrently and drive accountability and follow-through without formal authority.
• Analytical fluency, including comfort building financial models, synthesizing data from multiple sources, and translating analysis into executive-level insights.
• Proficiency in Excel, PowerPoint or Google Slides, and modern data and collaboration tools; ability to independently build and present executive-grade materials.
• Strong executive presence and interpersonal skills, with the ability to engage credibly with C-suite leaders, Board members, and advisors.
• Strong AI fluency and a clear point of view on applying modern AI tools to executive-level work; daily, hands-on use of leading LLMs and AI assistants for drafting, research, synthesis, and analysis.
• Understanding of how to embed AI into operating rhythms to improve planning, reporting, and communications.
• Experience owning or significantly contributing to operating cadence design, annual planning cycles, and company-level goal-setting processes.
• Familiarity with OKR, V2MOM, or other goal-setting processes and company-level annual planning cycles.
• High judgment, discretion, and alignment with CEO priorities; ability to build trust across the ELT, Board, and external stakeholders.
• Ability to improve the effectiveness of the CEO and ELT by removing friction, creating clarity, and accelerating important work.
• Exceptional communication skills, including precision, clarity, and adaptability across formats and audiences.
• Ability to treat AI fluency as a core competency and actively build AI into the Office of the CEO’s operations.
• Comfort with ambiguity, ability to create structure where it does not exist, and resilience in a fast-moving environment.
• Curiosity, intellectual humility, willingness to seek and use feedback, adaptability, and comfort challenging assumptions and working in unfamiliar areas.
• Ability to be highly responsive outside normal business hours, including Sunday evenings.

Nice To Haves

• MBA from a top-tier program.
• Familiarity with customer success, post-sale SaaS, or the broader customer success technology landscape.
• Hands-on experience building AI workflows, custom GPTs, agents, or lightweight automations to support executive work or team operations.
• Prior exposure to M&A due diligence or post-merger integration, and experience working with private equity sponsors.

Responsibilities

• Develop and deliver CEO communications, including presentations, scripts, talking points, and messaging for internal meetings, conferences, customer engagements, and stakeholder interactions.
• Prepare the CEO and other executives for public speaking engagements and media appearances.
• Manage the preparation, vetting, and follow-through for CEO speaking requests in partnership with Marketing.
• Draft company-wide announcements and CEO thought leadership content in the CEO’s voice, including newsletters, blogs, and LinkedIn posts.
• Partner with Marketing and PR on press releases, books, and other external media.
• Coordinate CEO-led cultural initiatives, including Childlike Joy videos and other programs.
• Set agendas, facilitate discussions, and manage follow-through for executive team meetings, offsites, and deep dives, ensuring decisions and actions have clear owners.
• Organize the annual calendar of key meetings, including Board meetings, executive offsites, QBRs, All Hands, Weekly Huddles, ELT meetings, and weekly operations meetings; coordinate logistics, agendas, and follow-up with the events team and other Chiefs of Staff.
• Attend strategic meetings, conferences, and offsites with the CEO; prepare for meetings, capture decisions and timelines, and manage follow-through.
• Own the narrative, content, and coordination for Board decks, Board letters, and investor materials, and prepare the CEO for high-stakes Board meetings.
• Support logistics and preparation for the CEO’s weekly Board Working Team call; manage Board document distribution in Box and serve as the day-to-day point of contact for the Vista team.
• Lead the annual strategic planning process in partnership with Finance, the CFO, and ELT, translating strategic priorities into resource and investment decisions for CEO and CFO review.
• Own and manage the V2MOM process, including ELT-level definition and support for cascading the process throughout the organization; track progress mid-cycle and report at the end of the cycle.
• Provide analytical and project management support for M&A and strategic partnership evaluations as needed.
• Drive high-priority, cross-functional CEO initiatives from problem definition and team assembly through stakeholder alignment, progress monitoring, and delivery.
• Build and maintain executive decision-making resources, including performance dashboards, KPI tracking, and business reviews that synthesize cross-functional and business-unit data for the ELT.
• Embed AI into planning, reporting, and analysis workflows to improve speed and quality.
• Serve as a shared strategic resource to business-unit GMs and functional leaders, providing executive visibility into issues that cross organizational boundaries.
• Remain highly responsive across email, Slack, text, and phone, including outside normal business hours and Sunday evenings.
• Travel locally, domestically, and internationally to be onsite with the CEO as needed; occasional travel for team meetings, training, or company events is also required.

Benefits

• Annual bonus eligibility and participation in Gainsight’s equity program.
• Comprehensive benefits package, including fully covered employee-only medical premiums, dental coverage, and vision coverage.
• Flexible PTO.
• 401(k) plan.
• Remote work options.
• $10,000 lifetime fertility stipend.
• Access to coworking spaces around the globe.
• Dedicated Recharge Holidays: one long weekend each quarter.
• Mentoring and career development opportunities.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior