Strategic Technical Project Manager

About the Role

The ideal candidate will have a strong technical background, with experience in managing enterprise-grade software or SaaS implementations. You will be working closely with executive stakeholders to define success criteria, governance structures, and outcome validation frameworks. Your ability to communicate technical concepts to non-technical stakeholders and drive disciplined scope control, change management, and financial oversight will be essential to your success in this role.

Gainsight's CustomerOS platform is at the forefront of the AI-driven customer success industry, and as a Strategic Technical Project Manager, you will play a key role in shaping the future of customer success. With over 2,000 companies trusting Gainsight's applications and AI agents to drive learning, adoption, community connection, and success for their customers, this is an opportunity to be part of a company that is making a significant 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 customers and internal teams to shape AI agent use cases into clear delivery plans, ensuring business problems are translated into practical, deployable workflows.
• 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.
• Monitor post-deployment performance signals and drive structured follow-up actions to improve adoption, stability, trust, and measurable business outcomes.

What We Are Looking For

• 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.
• Strong technical skills, with the ability to guide architectural discussions and proactively mitigate delivery risk.
• Experience working with cross-functional teams, including Sales, Customer Success, Solution Architecture, Product, and Engineering.
• Strong communication and interpersonal skills, with the ability to communicate technical concepts to non-technical stakeholders.
• Experience with project management tools and methodologies, such as Agile or Waterfall.
• Strong analytical and problem-solving skills, with the ability to drive disciplined scope control, change management, and financial oversight.
• Experience working in a fast-paced, evolving product environment, with the ability to adapt to changing priorities and requirements.

Nice to Have

• Experience working with AI-driven customer success platforms, such as Gainsight's CustomerOS.
• Knowledge of cloud-based technologies, such as AWS or Azure.
• Experience working with DevOps tools, such as Jenkins or Docker.
• Certification in project management, such as PMP or Scrum Master.

Benefits and Perks

• Competitive salary and benefits package.
• Opportunity to work with a leading company in the AI-driven customer success industry.
• Collaborative and dynamic work environment, with a team of experienced professionals.
• Flexible remote work arrangements, with the ability to work from anywhere in the United States.
• Professional development opportunities, with access to training and certification programs.
• Recognition and reward programs, with opportunities for career advancement and growth.
• Comprehensive health and wellness package, including medical, dental, and vision coverage.
• Generous paid time off policy, with vacation days, sick leave, and holidays.

• Develop a strong understanding of AI-driven customer success platforms, such as Gainsight's CustomerOS, to increase your chances of standing out as a candidate.
• Highlight your experience working with cross-functional teams, including Sales, Customer Success, Solution Architecture, Product, and Engineering, to demonstrate your ability to collaborate and drive aligned delivery.
• Be prepared to showcase your technical skills, including your ability to guide architectural discussions and proactively mitigate delivery risk, during the interview process.
• Emphasize your experience working in fast-paced, evolving product environments, and your ability to adapt to changing priorities and requirements, to demonstrate your flexibility and resilience.
• Consider obtaining certification in project management, such as PMP or Scrum Master, to demonstrate your expertise and commitment to the field.
• Prepare examples of your experience driving disciplined scope control, change management, and financial oversight, to demonstrate your ability to manage complex projects and deliver results.
• Research Gainsight's company culture and values, and be prepared to discuss how your skills and experience align with their mission and vision.