Strategic Technical Project Manager, AI Deployments

Gainsight•Tallahassee, FL

11d•$150,000 - $160,000•Remote

About The Position

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.

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.
Willingness to travel up to 10–15%.

Nice To Haves

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).

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.
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.