Chief of Staff, CEO Remote (anywhere in United States)

We’re building the AI-driven future of customer success, from retention to growth!

We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s 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:

We’re looking for a full-time Chief of Staff to join our Executives team reporting to the Chief Executive Officer. This role is a remote role based in the USA.

In this role, you’ll play a key role in amplifying the CEO’s impact and keeping the executive team aligned by owning the executive operating rhythm, driving cross-functional initiatives, and authoring the CEO’s 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 You'll 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 year’s 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 CEO’s 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 We're Looking For:

5-10 years of related experience and a Bachelor’s 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 executive’s 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 doesn’t exist, makes progress with imperfect information, and stays resilient in a fast-moving environment

Naturally curious and intellectually humble: brings a learner’s 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 You’ll 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 $215,000 – $235,000 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. In addition to base pay, this role is eligible for an annual bonus and participation in Gainsight’s 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 $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll 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, we’re 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, we’d love to hear from you.

Additional Information:

We’re 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 askTS@gainsight.com.

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.