Strategic Technical Project Manager

GainsightGainsight·Remote(USA - FL - Remote)
Project Management

WFA Digital Insight

The demand for skilled project managers in the tech industry has surged, with a 25% increase in remote project management roles in the past year. As companies like Gainsight pioneer AI-driven customer success solutions, the need for strategic technical project managers who can navigate complex stakeholder environments and drive measurable impact has never been more pressing. With the market expected to continue its upward trend, professionals with a strong background in technical project management and a keen understanding of AI-driven solutions are in high demand. Gainsight, a leader in customer success platforms, is seeking a talented individual to fill this critical role, offering a unique opportunity to work with a cutting-edge technology stack and contribute to the company's mission to revolutionize customer success. Before applying, candidates should be prepared to showcase their technical expertise, project management acumen, and ability to thrive in fast-paced, evolving product environments.

Job Description

About the Role

The Strategic Technical Project Manager role at Gainsight is a remote, full-time position that plays a vital part in driving the success of large-scale, high-visibility customer engagements within the Professional Services team. Reporting to the Director, PMO, this role is responsible for leading complex, multi-workstream implementations from contract signature through validated business outcomes. The ideal candidate will have a strong background in strategic project leadership, executive stakeholder alignment, and disciplined scope and financial management, as well as the technical fluency needed to guide architectural discussions and proactively mitigate delivery risk.

As a key member of the Professional Services team, the Strategic Technical Project Manager will work closely with cross-functional teams, including Sales, Customer Success, Solution Architecture, Product, and Engineering, to ensure aligned delivery and drive customer success. This role requires occasional travel for team meetings, training, or company events.

The Gainsight CustomerOS platform is at the forefront of the AI-driven customer success revolution, and this role offers a unique opportunity to contribute to the company's mission to shape the future of customer success. With more than 2,000 companies trusting Gainsight's applications and AI agents to drive learning, adoption, community connection, and success for their customers, the successful candidate will be part of a team that is making a real impact in the industry.

What You Will Do

  • Own end-to-end accountability for complex, multi-workstream customer engagements, including scope, timelines, budget, and risk management
  • 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
  • Lead steering committees and executive status reviews, communicating progress, risks, and outcome alignment
  • Develop reusable playbooks, governance frameworks, and strategic delivery standards to elevate the broader Professional Services practice
  • Mentor Senior TPMs and contribute to leadership capability within the team

What We Are 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 with cross-functional teams, including Sales, Customer Success, Solution Architecture, Product, and Engineering
  • Excellent communication, leadership, and problem-solving skills
  • Ability to work in a fast-paced, evolving product environment and thrive in a remote work setting

Nice to Have

  • Experience with AI-driven customer success solutions and platforms
  • Knowledge of cloud-based software development and deployment
  • Familiarity with agile project management methodologies and tools
  • Certification in project management, such as PMP or Agile

Benefits and Perks

  • Competitive salary and benefits package
  • Opportunity to work with a cutting-edge technology stack and contribute to the company's mission to revolutionize customer success
  • Collaborative and dynamic work environment with a team of experienced professionals
  • Flexible remote work arrangements and occasional travel opportunities
  • Professional development and growth opportunities, including training and certification programs
  • Access to the latest tools and technologies, including AI-driven customer success platforms
  • Recognition and reward programs for outstanding performance and contributions

How to Stand Out

  • Develop a strong understanding of AI-driven customer success solutions and platforms to stand out in the application process
  • Showcase your technical expertise and project management acumen through specific examples and case studies
  • Highlight your ability to work in a fast-paced, evolving product environment and thrive in a remote work setting
  • Emphasize your experience partnering with cross-functional teams and executive stakeholders to drive customer success
  • Be prepared to discuss your approach to risk management and mitigation in complex stakeholder environments
  • Research the company's technology stack and be prepared to ask informed questions during the interview process
  • Consider creating a portfolio or repository of your work to demonstrate your skills and experience to potential employers

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