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 Senior Program Manager, People Programs & AI, to join our People team reporting to the VP, Center of Excellence. This role is a remote role based in the USA.

In this role, you'll play a key role in improving the effectiveness, scalability, and innovation of the HR organization by leading complex, cross-functional initiatives and identifying opportunities to leverage AI and automation across HR processes and workflows. This is a great opportunity for someone who thrives in an ambiguous, fast-changing, highly matrixed environment and enjoys working cross-functionally with teams like HR Business Partners, Talent Acquisition, Talent Management, Total Rewards, and People Operations. The ideal candidate brings strong skills in program and transformation management, AI-enabled process optimization, and stakeholder management and influence.

What You'll Do:

HR Program & Transformation Management

Lead complex, cross-functional HR initiatives from planning through execution.
Develop project plans, timelines, governance structures, risk mitigation plans, and success metrics for enterprise HR programs.
Coordinate stakeholders across multiple HR functions to drive alignment, accountability, and execution.
Monitor program progress, identify risks and dependencies, and proactively drive resolution.
Facilitate working sessions, steering committees, and executive updates for key initiatives.
Support change management activities associated with new HR programs, processes, and operating models.
Document and standardize processes, lessons learned, and best practices across HR programs.

AI Enablement & Process Optimization

Assess HR workflows and processes to identify opportunities for automation, AI adoption, and operational improvements.
Partner with HR teams to map current-state and future-state processes.
Research emerging AI tools, capabilities, and industry practices relevant to HR.
Support the design, testing, implementation, and adoption of AI-enabled solutions across HR functions.
Measure and track the impact of AI and automation initiatives, including efficiency gains, employee experience improvements, and adoption metrics.
Develop recommendations for process improvements that increase scalability and reduce manual work.
Help build AI literacy and change readiness across the HR organization.

Stakeholder Management & Collaboration

Build strong partnerships across HR functions and business stakeholders.
Influence without direct authority to drive progress on shared goals.
Translate complex concepts into clear communications and actionable plans.
Balance competing priorities while maintaining focus on strategic outcomes and business value.
Serve as a trusted partner to HR leaders on transformation initiatives and operational improvements.

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+ years of experience in Human Resources, People Operations, Talent, Organizational Effectiveness, or related people-focused functions.
6–10+ years of experience in program management, HR transformation, consulting, business operations, HR operations, or related fields.
Strong understanding of how generative AI and emerging technologies can be applied to improve employee, manager, and HR team experiences.
Demonstrated experience leading complex cross-functional initiatives with multiple stakeholders.
Strong project and program management skills, including planning, execution, governance, and risk management.
Experience driving process improvement and organizational change initiatives.
Excellent communication, facilitation, and stakeholder management skills.
Ability to influence and drive outcomes in a highly matrixed environment.
Strong analytical and problem-solving capabilities.

Nice-to-have skills or experience:

Experience supporting HR, People Operations, Talent, or organizational effectiveness functions.
Experience evaluating or implementing AI, automation, workflow, or productivity solutions.
Familiarity with HR technologies and employee lifecycle processes.
Experience with process mapping, change management, or operational excellence methodologies.

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 $120,000 - $150,000 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 recruiting@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.