Strategic Technical Project Manager, AI Deployments

Gainsight is an AI-powered customer success company providing solutions for retention, growth, and customer journey management. The Strategic Technical Project Manager will own complex, multi-workstream customer engagements, leading AI agent and human agent solution deployments from contract signature through validated business outcomes. The role will manage stakeholders, scope, financials, risks, governance, technical delivery, and post-deployment performance across cross-functional teams.

Responsibilities:

• 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

Requirements:

• 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
• 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)