Chief of Staff, CEO

The role

The Chief of Staff will amplify the CEO's impact and keep the executive team aligned. This person will own the executive operating rhythm, drive cross-functional initiatives, and author the CEO's internal and external communications.

What you will do

• Develop and deliver CEO communications including presentations, scripts, and messaging.
• Prepare the CEO and executives for public speaking and media appearances.
• Draft company-wide announcements and CEO thought leadership.
• Coordinate CEO-driven cultural initiatives.
• Set the agenda and drive follow-through for executive team meetings and offsites.
• Organize the fiscal year's key meeting calendar including Board meetings and QBRs.
• Own content and coordination for board decks and investor materials.
• Run the annual strategic planning process in partnership with Finance and the ELT.
• Own and run the V2MOM process.
• Drive high-priority, cross-functional CEO initiatives end-to-end.

Required qualifications

• 5-10 years of related experience
• 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
• Strong structured thinking
• Ability to manage multiple complex, cross-functional workstreams concurrently
• Analytical fluency including comfort building financial models
• Proficiency in Excel, PowerPoint/Google Slides, and modern data and collaboration tools
• Strong executive presence and interpersonal skills
• Strong AI fluency and daily, hands-on use of leading LLMs and AI assistants
• Experience owning or contributing to operating cadence design, annual planning cycles, and company-level goal-setting processes
• Familiarity with OKR/V2MOM/goal-setting processes

Nice to have

• MBA from a top-tier program
• Familiarity with customer success, post-sale SaaS, or the broader CS technology landscape
• Hands-on experience building AI workflows, custom GPTs, agents, or lightweight automations
• Prior exposure to M&A due diligence or post-merger integration work
• Experience working with Private Equity sponsors

Benefits

• Fully covered medical premiums (employee-only)
• Flexible PTO
• 401(k) plan
• Dental and vision coverage
• Remote work options
• $10,000 lifetime fertility stipend
• Access to coworking spaces around the globe
• Recharge Holidays - one long weekend each quarter

About the company

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.