Principal Strategic Engagement Manager

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 Principal Strategic Engagement Manager to join our Services team  reporting to the Senior Manger, Technical Services. This role is a remote role based in The United States. 

In this role, you’ll play a key role in driving strategic impact for Gainsight’s most complex global client partnerships by leading large-scale programs, aligning executive stakeholders, and delivering measurable business outcomes. This is a great opportunity for someone who thrives in highly complex, matrixed environments and enjoys working cross-functionally with teams like Solution Architects, Technical Account Managers, Customer Account Managers, and Customer Success Managers. The ideal candidate brings strong skills in enterprise program management, executive stakeholder engagement, and cross-functional leadership.

What You'll Do: 

• Architect, orchestrate, and ensure delivery of large-scale, cross-functional initiatives that drive measurable business outcomes and maximize client success and Gainsight value.

• Guide the design of scalable program governance, delivery, and measurement approaches, ensuring optimal resource deployment, margin optimization, and client satisfaction.

• Represent Gainsight as an executive sponsor in critical customer forums, executive business reviews, and SteerCo sessions, influencing decisions and building customer advocacy.

• Represent Gainsight as the executive point of escalation, negotiating complex issues and ensuring client relationships remain strong and mutually beneficial.

• Partner with executive sponsors (both client and Gainsight) to define both short and long-term program roadmaps and drive alignment between client business outcomes and Gainsight’s offerings.

• Build and nurture trusted, executive–level relationships within client organizations, advocating for strategic partnership and executive alignment.

• Support the definition of long-term account strategy by anticipating evolving client business objectives and proactively identifying opportunities for value delivery, innovation, and expansion.

• Partner with internal stakeholders to identify and secure strategic cross-functional resources, influence product direction, and drive company-wide alignment for key accounts.

• Serve as a visible leader and mentor within the Professional Services organization—coaching, developing, and elevating program management excellence and thought leadership.

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: 

• 10+ years of relevant experience in enterprise program or project management, professional services, management consulting, or customer success, with a track record of managing global, strategic accounts. Bachelor’s degree required; advanced degree (e.g., MBA, MS in Engineering) or equivalent experience preferred.

• Demonstrated success leading large service contract programs with Fortune 500 clients, including experience with multi-year, multi-business-unit engagements.

• Executive-level stakeholder management and advisory experience (C-suite engagement required).

• Proven ability to design and scale program and project management frameworks or methodologies across a professional services organization.

• Experience leading and mentoring others, fostering talent development at scale.

• Outstanding executive communication, strategic thinking, negotiation, and influencing skills.

• Expert proficiency in program/portfolio management tools, CRM software, and data analytics platforms.

• Willingness to travel as needed (up to 20%), including global travel.

• PMP, PgMP, or similar advanced project/program management certification.

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 $140,000 – $150,000 USD annually. This role is also eligible for commission based on performance and participation in Gainsight’s equity program. Actual compensation may vary based on factors such as skills, experience, and location. 

• 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 let the recruiting team know. 

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.