Gainsight Chief of Staff to the CEO at Gainsight responsible for amplifying CEO impact and aligning the executive team. Owns executive operating rhythm, drives cross-functional initiatives, and authors CEO communications.
Responsibilities
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.
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.
Qualification
Exceptional written communicationStrong structured thinkingAnalytical fluencyProficiency in ExcelTrusted partner
Required
5-10 years of related experience and a Bachelor’s degree (or equivalent experience), with 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, with demonstrated experience writing in a senior executive’s voice across formats: board materials, all-hands narratives, internal announcements, LinkedIn and thought leadership, and customer-facing keynotes
Strong structured thinking, with the ability to synthesize ambiguous information into clear recommendations and crisp, executive-ready materials
Demonstrated ability to manage multiple complex, cross-functional workstreams concurrently, driving 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/Google Slides, and modern data and collaboration tools, with the ability to build and present executive-grade materials independently
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 how to apply modern AI tools to executive-level work; daily, hands-on user of leading LLMs and AI assistants for drafting, research, synthesis, and analysis
Understanding of how to embed AI into operating rhythms to make planning, reporting, and communications faster and higher-quality
Experience owning or significantly contributing to operating cadence design, annual planning cycles, and company-level goal-setting processes
Familiarity with OKR/V2MOM/goal-setting processes and annual planning cycles at the company level
Trusted partner: operates as a genuine extension of the CEO with high judgment, high discretion, and deep alignment on priorities; builds trust across the ELT, Board, and external stakeholders through consistent delivery and sound judgment
