TL;DR

Strategic Technical Project Manager (AI): Driving the success of large-scale customer engagements within Professional Services by leading complex implementations from contract signature through validated business outcomes with an accent on engagement governance, aligning executive stakeholders, and orchestrating cross-functional execution. Focus on disciplined scope control, change management, and financial oversight across strategic engagements, ensuring solutions are delivered on time and within budget.

Location: Remote (USA - FL - Remote USA - TX - Remote USA - TN - Remote USA - SC - Remote USA - RI - Remote)

Salary: $150,000 – $160,000 USD annually.

Company

Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies.

What you will do

  • Own end-to-end accountability for complex 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.
  • Drive disciplined scope control, change management, and financial oversight across strategic engagements.
  • Coordinate cross-functional teams to ensure aligned delivery.
  • Lead steering committees and executive status reviews, communicating progress, risks, and outcome alignment.
  • Develop reusable playbooks, governance frameworks, and strategic delivery standards.

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 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.
  • Exceptional communication skills for both technical and executive audiences.

Culture & Benefits

  • Comprehensive benefits package including fully covered medical premiums, 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.
  • Dedicated Recharge Holidays - one long weekend each quarter to relax and reset.
  • Guided by values and a mission to be living proof you can win in business while being Human-First.
  • Passionate about helping teammates learn, grow, and thrive.