Chief of Staff, CEO

Were building the AI-driven future of customer success from retention to growth!

Were building the AI-driven future of customer success from retention to growth! Gainsight is the AI-powered retention engine behind the worlds most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2000 companies trust Gainsights applications and AI agents to drive learning adoption community connection and success for their customers. To explore how our suite of solutions is shaping the future of customer success check out the link.

About This Role:

Were looking for a full-time Chief of Staff in the San Francisco Bay area to join our Executives team reporting to the Chief Executive Officer. This role is a hybrid role based in the USA.

In this role youll play a key role in amplifying the CEOs impact and keeping the executive team aligned by owning the executive operating rhythm driving cross-functional initiatives and authoring the CEOs internal and external communications. This is a great opportunity for someone who thrives in a high-visibility fast-moving AI-forward environment and enjoys working cross-functionally with teams like the Executive Leadership Team the Board Finance and Marketing. The ideal candidate brings strong skills in executive writing strategic planning and AI fluency.

What Youll Do:

CEO Communications (Internal & External)

• Develop and deliver high-impact CEO communications including presentations scripts talking points and messaging for internal meetings industry conferences customer engagements and stakeholder interactions.

• Prepare the CEO and other executives for public speaking engagements and media appearances. Own pre-prep vetting and follow-through on inbound and outbound CEO speaking requests in partnership with Marketing.

• Draft company-wide announcements (executive hires departures org changes M&A) and CEO thought leadership in his voice newsletters blogs LinkedIn. Partner with Marketing and PR on press releases books and other external media.

• Coordinate CEO-driven cultural initiatives including Childlike Joy videos and other programs.

Executive Team Operations

• Set the agenda drive discussion and own follow-through for executive team operating meetings offsites and deep dives. Ensure clear ownership of decisions and actions.

• Organize and facilitate the fiscal years key meeting calendar Board meetings executive offsites QBRs All Hands Weekly Huddles ELT and weekly operations meetings partnering with the events team and other Chiefs of Staff on logistics agenda and follow-up.

• Attend strategic meetings conferences and offsites with the CEO. Drive prep capture decisions and timelines and own follow-through.

Board & Investor Engagement

• Own the narrative content and coordination for board decks board letters and investor materials. Ensure the CEO is fully prepared for high-stakes Board moments.

• Support logistics and prep for the CEOs weekly Board Working Team (BWT) call. Manage Board document distribution in Box and serve as the day-to-day point of contact for the Vista team.

Company-Level Strategy & Annual Planning

• Run the full life cycle of the annual strategic planning process (AOP) in partnership with Finance the CFO and ELT. Translate strategic priorities into resource and investment decisions for CEO and CFO review.

• Own and run the V2MOM process defining at the ELT level and supporting cascading throughout the rest of the organization. Drive mid-cycle tracking and end-of-cycle reporting.

• Provide analytical and project management support on M&A and strategic partnership evaluations as needed.

Project Ownership

• Drive high-priority cross-functional CEO initiatives end-to-end. Define the problem assemble the working team manage stakeholder alignment and monitor progress through to delivery.

• Build and maintain the data layer for executive decision-making performance dashboards KPI tracking and business reviews that synthesize cross-functional and BU-level data for the ELT. Embed AI into these workflows to make planning reporting and analysis faster and higher quality.

• Serve as a shared strategic resource to BU GMs and functional leaders providing executive visibility on issues that span organizational boundaries.

Hyper-Responsiveness and Flexibility

• Be hyper-responsive across email Slack text and phone including outside of normal business hours and Sunday evenings to prepare for the business week.

• Travel locally domestically and internationally to be onsite with the CEO as needed.

This is not a complete list of responsibilities and the scope of the role may evolve with the needs of the team and business. This role will require occasional travel for team meetings training or company events.

What Were Looking For:

• 5-10 years of related experience and a Bachelors degree (or equivalent experience) with a proven track record in a Chief of Staff strategy business operations management consulting investment banking venture capital or private equity role

• Exceptional written communication with demonstrated experience writing in a senior executives voice across formats: board materials all-hands narratives internal announcements LinkedIn and thought leadership and customer-facing keynotes

• Strong structured thinking with the ability to synthesize ambiguous information into clear recommendations and crisp executive-ready materials

• Demonstrated ability to manage multiple complex cross-functional workstreams concurrently driving accountability and follow-through without formal authority

• Analytical fluency including comfort building financial models synthesizing data from multiple sources and translating analysis into executive-level insights

• Proficiency in Excel PowerPoint/Google Slides and modern data and collaboration tools with the ability to build and present executive-grade materials independently

• Strong executive presence and interpersonal skills with the ability to engage credibly with C-suite leaders Board members and advisors

• Strong AI fluency and a clear point of view on how to apply modern AI tools to executive-level work; daily hands-on user of leading LLMs and AI assistants for drafting research synthesis and analysis

• Understanding of how to embed AI into operating rhythms to make planning reporting and communications faster and higher-quality

• Experience owning or significantly contributing to operating cadence design annual planning cycles and company-level goal-setting processes

• Familiarity with OKR/V2MOM/goal-setting processes and annual planning cycles at the company level

• Trusted partner: operates as a genuine extension of the CEO with high judgment high discretion and deep alignment on priorities; builds trust across the ELT Board and external stakeholders through consistent delivery and sound judgment

• Force multiplier: makes the CEO and ELT more effective by removing friction creating clarity and accelerating the most important work across the organization

• Exceptional communicator: writes with precision clarity and voice and adapts seamlessly across formats from a tightly crafted board letter to an inspiring all-hands narrative

• Applies AI as a core competency: actively builds AI into how the Office of the CEO operates treats AI fluency as a professional standard and helps raise the bar across the ELT

• Comfortable with ambiguity: defines structure where it doesnt exist makes progress with imperfect information and stays resilient in a fast-moving environment

• Naturally curious and intellectually humble: brings a learners mindset to every problem actively seeks feedback adapts quickly and is equally comfortable challenging their own assumptions and operating in unfamiliar territory

Nice-to-have skills or experience:

• 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 to support executive work or team operations (strong plus)

• Prior exposure to M&A due diligence or post-merger integration work and experience working with Private Equity sponsors

Why Youll Love It Here:

Gainsight is a place where innovation is shaped through collaboration curiosity and a shared focus on solving real-world problems. With a growing suite of products across customer success product experience community education and AI-powered relationship intelligence we continue to evolve with the needs of our customers. When people with diverse strengths a strong sense of community and true passion for our mission come together they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability trust and support that people need - not just to do the job but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few:

Our Compensation and Benefits: At Gainsight we believe great work happens when teammates feel fully supported.

• The starting base salary range for this role is $215000 $235000 USD annually. Actual compensation may vary based on factors such as skills experience and addition to base pay this role is eligible for an annual bonus and participation in Gainsights equity program.

• We offer a comprehensive benefits package including fully covered medical premiums (employee-only) flexible PTO 401(k) plan dental and vision coverage and remote work options. Additional benefits include a $10000 lifetime fertility stipend and access to coworking spaces around the globe. Youll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset.

Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First. Learn more here.

Our Growth Opportunities: From mentoring to career development opportunities were passionate about helping our teammates learn grow and thrive.

Our Parody Videos: No explanation needed. Just watch them here!

If this sounds like the right role for you wed love to hear from you.

Additional Information:

Were committed to creating an inclusive fair and transparent hiring process. As an equal opportunity employer we celebrate diversity and are committed to creating a welcoming experience for all candidates.

If you require accommodations or have questions about how your personal data will be used during the hiring process please contact

If you are based in San Francisco we will consider qualified applicants with arrest and conviction records in accordance with the San Francisco Fair Chance Ordinance.

Required Experience:

Senior IC