Chief of Staff, CEO

Gainsight

. Report to the Chief Executive Officer and amplify the CEO’s impact .

Posted 10/15/2026full-timeRemote • California • United StatesLead💰 $215,000 - $235,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates strong executive presence and exceptional written communication skills, with a proven ability to manage complex, cross-functional workstreams and drive accountability. Proficient in embedding AI into operational processes and experienced in strategic planning and performance reporting.

Highest-signal resume keywords

Chief Of Staff ExperienceExecutive CommunicationAI FluencyFinancial ModelingOKR/V2MOM Familiarity

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Financial ModelingData SynthesisCross-Functional ManagementStrategic PlanningPerformance Reporting

Soft Skills

Exceptional Written CommunicationStrong Executive PresenceInterpersonal SkillsStructured ThinkingHigh Judgment

Tools & Technologies

ExcelPowerPointGoogle SlidesAI AssistantsCollaboration Tools

Certifications & Qualifications

Bachelor’s DegreeMBA (Nice-to-Have)

Industry Keywords

Chief Of StaffBusiness OperationsManagement ConsultingInvestment BankingPrivate Equity

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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