Chief of Staff, CEO

Gainsight•Sacramento, CA

19h•$215,000 - $235,000•Remote

About The Position

Gainsight is seeking a full-time Chief of Staff to join its Executives team. The role reports to the Chief Executive Officer and is remote in the USA. The Chief of Staff amplifies the CEO’s impact and keeps the executive team aligned by owning the executive operating rhythm, driving cross-functional initiatives, and authoring internal and external CEO communications. The role works across the Executive Leadership Team, Board, Finance, Marketing, and other teams in a high-visibility, fast-moving, AI-forward environment. The position owns CEO communications, executive team operations, Board and investor engagement, company-level strategy and annual planning, and high-priority cross-functional projects. It supports the CEO at strategic meetings, conferences, and offsites, and builds data and AI-enabled workflows for executive decision-making. The role requires high responsiveness, including outside normal business hours and Sunday evenings, and travel locally, domestically, and internationally as needed. The scope may evolve with the needs of the team and business; occasional travel may be required for team meetings, training, or company events.

Requirements

5–10 years of related experience and a bachelor’s degree or equivalent experience.
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 board materials, all-hands narratives, internal announcements, LinkedIn and thought leadership, and customer-facing keynotes.
Strong structured thinking and 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 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 the speed and quality of 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 through consistent delivery and sound judgment.
Ability to make the CEO and ELT more effective by removing friction, creating clarity, and accelerating important organizational work.
Exceptional communication skills, including precision, clarity, voice, and adaptability across formats.
Ability to actively incorporate AI into the Office of the CEO’s work and help raise AI fluency across the ELT.
Comfort with ambiguity, including defining structure where it does not exist, making progress with imperfect information, and remaining resilient in a fast-moving environment.
Curiosity, intellectual humility, learner’s mindset, openness to feedback, adaptability, and willingness to challenge assumptions and work in unfamiliar territory.
Ability to be hyper-responsive, including outside normal business hours and 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 work, and experience working with private equity sponsors.

Responsibilities

Develop and deliver 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; manage the preparation, vetting, and follow-through for CEO speaking requests in partnership with Marketing.
Draft company-wide announcements and CEO thought leadership in the CEO’s voice, including newsletters, blogs, and LinkedIn content; 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.
Set agendas, drive discussions, and manage follow-through for executive team operating meetings, offsites, and deep dives, ensuring ownership of decisions and actions.
Organize and facilitate the fiscal year’s key meeting calendar, including Board meetings, executive offsites, QBRs, All Hands, Weekly Huddles, ELT, and weekly operations meetings, coordinating logistics, agendas, and follow-up with the events team and other Chiefs of Staff.
Attend strategic meetings, conferences, and offsites with the CEO; drive preparation, capture decisions and timelines, and own follow-through.
Own the narrative, content, and coordination for Board decks, Board letters, and investor materials, and prepare the CEO for high-stakes Board moments.
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.
Run 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 run the V2MOM process at ELT level and support its cascading through the organization; drive mid-cycle tracking and end-of-cycle reporting.
Provide analytical and project management support for M&A and strategic partnership evaluations as needed.
Drive high-priority, cross-functional CEO initiatives end-to-end, including defining problems, assembling working teams, aligning stakeholders, and monitoring progress through delivery.
Build and maintain executive decision-making data, performance dashboards, KPI tracking, and business reviews that synthesize cross-functional and business-unit data for the ELT; embed AI to improve the speed and quality of planning, reporting, and analysis.
Serve as a shared strategic resource to business-unit general managers and functional leaders, providing executive visibility on issues spanning organizational boundaries.
Respond across email, Slack, text, and phone, including outside 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, and occasionally travel for team meetings, training, or company events.