Chief of Staff, CEO

This is a fully remote position, open to applicants in California.

📋 Description

• Report directly to the Chief Executive Officer and enhance the CEO’s influence.

• Oversee the executive operating rhythm, ensuring alignment among the executive team.

• Create presentations, scripts, talking points, and messaging for the CEO.

• Prepare the CEO and other executives for public speaking engagements and media appearances.

• Coordinate CEO speaking requests in collaboration with the Marketing team.

• Compose company-wide announcements and thought leadership content from the CEO.

• Collaborate with Marketing and PR on press releases, publications, and external media engagements.

• Manage CEO-led cultural initiatives.

• Set agendas, facilitate executive meetings, and ensure follow-through on actions.

• Organize Board meetings, offsites, QBRs, All Hands, Weekly Huddles, ELT meetings, and operational meetings.

• Attend strategic meetings, conferences, and offsites with the CEO; document decisions and timelines.

• Prepare board decks, board letters, investor materials, and facilitate Board Working Team calls.

• Handle Board document distribution via Box and serve as the main point of contact for the Vista team on a daily basis.

• Lead the annual strategic planning process in partnership with Finance, the CFO, and ELT.

• Own and manage the V2MOM process and its reporting.

• Assist with M&A and evaluations of strategic partnerships.

• Propel high-priority, cross-functional initiatives driven by the CEO from start to finish.

• Develop executive dashboards, track KPIs, and prepare performance reports and business reviews.

• Incorporate AI into planning, reporting, and analytical workflows.

• Act as a strategic resource for business-unit GMs and functional leaders.

• Maintain high responsiveness via email, Slack, text, and phone, including outside standard business hours and Sunday evenings.

• Travel locally, nationally, and internationally to be onsite with the CEO as necessary.

• Occasionally travel for team meetings, training sessions, or company events.

⛳️ Requirements

• 5-10 years of relevant experience.

• Bachelor’s degree or equivalent experience.

• Demonstrated success in roles such as Chief of Staff, strategy, business operations, management consulting, investment banking, venture capital, or private equity.

• Outstanding written communication skills with experience in writing for senior executives.

• Strong structured thinking abilities and the capacity to distill ambiguous information into actionable recommendations.

• Capability to manage multiple complex, cross-functional workstreams and drive accountability without formal authority.

• Proficient analytical skills, including financial modeling and synthesizing data from various sources.

• Expertise in Excel, PowerPoint/Google Slides, and modern data and collaboration tools.

• Strong executive presence and interpersonal skills.

• High proficiency in AI, with daily hands-on experience using leading LLMs and AI assistants.

• Knowledge of embedding AI into operational rhythms.

• Familiarity with operating cadence design, annual planning cycles, and company-level goal-setting.

• Understanding of OKR/V2MOM and annual planning processes.

• High judgment, discretion, and alignment with the CEO's priorities.

• Comfort in navigating ambiguity and fast-paced environments.

• Nice-to-have: MBA from a prestigious program.

• Nice-to-have: Knowledge of customer success, post-sale SaaS, or CS technology.

• Nice-to-have: Experience in building AI workflows, custom GPTs, agents, or lightweight automations.

• Nice-to-have: Background in M&A due diligence or post-merger integration and experience with private equity sponsors.

🏝️ Benefits

• Eligibility for annual bonuses.

• Participation in Gainsight’s equity program.

• Fully covered medical premiums for employees only.

• Flexible PTO policy.

• 401(k) plan available.

• Dental and vision insurance coverage.

• Options for remote work.

• $10,000 lifetime fertility stipend.

• Access to coworking spaces worldwide.

• Dedicated Recharge Holidays—one long weekend every quarter.

• Opportunities for mentoring and career development.