Chief of Staff, CEO

Job not on LinkedIn

🔥 8 minutes ago

🏄 California – Remote

🏄 California – Remote

💵 $215k - $235k / year

⏰ Full Time

🔴 Lead

👩🏽‍✈️ Chief of Staff

👻 Ghost score 0%

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Gainsight

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

☁️ SaaS

🤝 B2B

🏢 Enterprise

💰 $52M Series E - Gainsight on 2017-05

SaaS • B2B • Enterprise

Gainsight is a SaaS company that provides a unified Customer Success platform and related products to help businesses retain, expand, and drive product adoption with their customers. Its offerings include Gainsight CS (customer success), Product Experience (in-app engagements and analytics), Customer Communities, Skilljar (customer education), and AI-powered agents and services (Staircase AI, Agent Studio, Gainsight MCP) that surface insights and automate customer success workflows. Gainsight positions itself as an enterprise-focused, AI-native solution for post-sales teams, emphasizing retention-as-a-service, integrated customer data, and scalability for CSMs and product teams.

📋 Description

• 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