Chief of Staff, CEO

The posting, as Gainsight wrote it

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 https://www.gainsight.com.

About This Role

We’re 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, 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 let

[…]
y 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 https://www.gainsight.com/company/.

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! https://www.youtube.com/playlist?list=PLB2Z_xLbXPiAcvQr28ggP2CndoSu29zq_

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.