Chief of Staff, CEO
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Job Description
Chief of Staff amplifying Gainsight CEO impact across communications, strategy, and executive operations. Driving planning, board engagement, and AI-enabled decision-making for a customer success platform.
Responsibilities:
- Report to the Chief Executive Officer and amplify the CEO’s impact
- Own the executive operating rhythm and keep the executive team aligned
- Develop CEO presentations, scripts, talking points, and messaging
- Prepare the CEO and executives for public speaking and media appearances
- Manage CEO speaking requests with Marketing
- Draft company-wide announcements and CEO thought leadership content
- Partner with Marketing and PR on press releases, books, and external media
- Coordinate CEO-driven cultural initiatives
- Set agendas, facilitate executive meetings, and own follow-through
- Organize Board meetings, executive offsites, QBRs, All Hands, Weekly Huddles, ELT meetings, and operations meetings
- Attend strategic meetings, conferences, and offsites with the CEO; capture decisions and timelines
- Own board decks, board letters, investor materials, and Board Working Team call preparation
- Manage Board document distribution in Box and act as the day-to-day point of contact for the Vista team
- Run the annual strategic planning process with Finance, the CFO, and ELT
- Own and run the V2MOM process and reporting
- Support M&A and strategic partnership evaluations
- Drive high-priority, cross-functional CEO initiatives end-to-end
- Build executive dashboards, KPI tracking, performance reporting, and business reviews
- Embed AI into planning, reporting, and analysis workflows
- Serve as a strategic resource to business-unit GMs and functional leaders
- Be hyper-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
- Occasionally travel for team meetings, training, or company events
Requirements:
- 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 and experience writing in a senior executive’s voice
- Strong structured thinking and ability to synthesize ambiguous information into clear recommendations
- Ability to manage multiple complex, cross-functional workstreams and drive accountability without formal authority
- Analytical fluency, including financial modeling and synthesizing data from multiple sources
- Proficiency in Excel, PowerPoint/Google Slides, and modern data and collaboration tools
- Strong executive presence and interpersonal skills
- Strong AI fluency; daily, hands-on use of leading LLMs and AI assistants
- Understanding of embedding AI into operating rhythms
- Experience with operating cadence design, annual planning cycles, and company-level goal-setting
- Familiarity with OKR/V2MOM and annual planning processes
- High judgment, discretion, and alignment with CEO priorities
- Comfort with ambiguity and fast-moving environments
- Nice-to-have: MBA from a top-tier program
- Nice-to-have: Familiarity with customer success, post-sale SaaS, or CS technology
- Nice-to-have: Experience building AI workflows, custom GPTs, agents, or lightweight automations
- Nice-to-have: M&A due diligence or post-merger integration and private equity sponsor experience
Benefits:
- Annual bonus eligibility
- Participation in Gainsight’s equity program
- 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
- Dedicated Recharge Holidays—one long weekend each quarter
- Mentoring and career development opportunities
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