Strategic Technical Project Manager, AI Deployments

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 Strategic Technical Project Manager to join our Professional Services team reporting to the Director, PMO. This role is a remote role based in The United States.

In this role, you'll play a key role in driving large-scale, complex, and high-visibility customer engagements within Professional Services from contract signature through validated business outcomes by operating as the overall engagement owner across multiple workstreams: aligning stakeholders, managing scope and financials, mitigating risk, and ensuring AI agent plus human agent solutions are deployed responsibly and effectively in production environments with clear success criteria, strong governance, milestone-based ramping, and ongoing iteration based on real-world performance. This is a great opportunity for someone who thrives in a customer-embedded delivery environment that requires close partnership with product teams and balances speed, technical feasibility, user trust, and business value, and enjoys working cross-functionally with teams like Sales, Customer Success, Solution Architecture, Product, and Engineering. The ideal candidate brings strong skills in strategic project leadership, stakeholder alignment, and disciplined execution.

What You'll Do:

• Own end-to-end accountability for complex, multi-workstream customer engagements, including scope, timelines, budget, and risk management.

• Partner with customers and internal teams to shape AI agent use cases into clear delivery plans, ensuring business problems are translated into practical, deployable workflows.

• Identify, create, and manage parallel workstreams — technical implementation (AI platform configuration, integrations, system access, AI agent workflow, reporting build) and oversee human agent readiness plan (staffing timelines, onboarding and training schedules, certifications)

• Partner with executive stakeholders to define success criteria, governance structures, and outcome validation frameworks.

• Translate business objectives into structured delivery plans, work breakdown structures, and cross-functional execution models.

• Drive disciplined scope control, change management, and financial oversight across strategic engagements.

• Coordinate cross-functional teams including Solution Architecture, Customer Success, Product, and Engineering to ensure aligned delivery.

• Identify and proactively mitigate risks across technical, operational, and organizational dimensions.

• Ensure technical solutions are architecturally sound by partnering with technical teams, without serving as the primary engineer.

• Monitor post-deployment performance signals and drive structured follow-up actions to improve adoption, stability, trust, and measurable business outcomes

• Mentor Senior TPMs and contribute to leadership capability within the team.

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. Travel is expected to be up to 10-15%, primarily for customer onsite engagements.

What We're Looking For:

• Bachelor’s degree in Computer Science, Engineering, or a related technical field (or equivalent experience) and 10+ years of relevant experience.

• 7+ years managing enterprise-grade software or SaaS implementations within Professional Services or Technical Consulting.

• Proven track record managing multi-workstream engagements with complex stakeholder environments and contract values exceeding $500K+.

• Strong project governance, financial management, and executive stakeholder alignment capabilities.

• Technical fluency in APIs, data models, and enterprise integrations sufficient to guide architectural discussions and manage risk.

• Experience partnering cross-functionally with Product and Engineering teams.

• Exceptional communication skills for both technical and executive audiences.

• Ability to operate effectively in fast-paced, evolving product environments.

• Willingness to travel up to 10–15%.

Nice to have skills or experience:

• Experience in a Field Delivery Engineering (FDE) or customer-embedded delivery model.

• Experience with business process outsourcing projects

• Experience implementing Customer Success, CRM, or enterprise SaaS platforms.

• Familiarity with AI-driven solutions, automation, or advanced analytics implementations.

• Project Management certification (PMP, PRINCE2, or equivalent).

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 $150,000 – $160,000 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.