Strategic Technical Project 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 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 the success of large-scale, high-visibility customer engagements within Professional Services by leading complex, multi-workstream implementations from contract signature through validated business outcomes. You ll ensure solutions are delivered on time, within scope, and aligned to measurable impact by owning end-to-end engagement governance, aligning executive stakeholders, and orchestrating cross-functional execution across Sales, Customer Success, Solution Architecture, Product, and Engineering. This is a great opportunity for someone who thrives in fast-paced, evolving product environments and enjoys working cross-functionally with executive stakeholders, Field Delivery Engineering (FDE), Product, Engineering, and Customer Success teams. The ideal candidate brings strong skills in strategic project leadership, executive stakeholder alignment, and disciplined scope and financial management, along with the technical fluency needed to guide architectural discussions and proactively mitigate delivery risk. 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. • Lead SteerCo and C-suite steering committees, executive QBRs, and status reviews - communicating progress, risks, and business outcome alignment directly to senior executive audiences. • 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 organisational dimensions. • Ensure technical solutions are architecturally sound by partnering with technical teams, without serving as the primary engineer. • Drive AI / agentic workflow deployments end-to-end - from scoping and design through go-live, adoption, and iteration - ensuring measurable business outcomes are achieved in production environments. • Develop reusable playbooks, governance frameworks, delivery standards, and methodology documentation that elevate the broader Professional Services practice - owning the creation of new standards, not just following existing ones. • Bring enterprise-grade delivery standards from large, complex organisational environments - applying structured governance and risk management to accelerate time-to-value for Gainsight's most strategic accounts. • 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. What We're Looking For: • Bachelor s degree (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 eff...