[Remote] Strategic Technical Project Manager
Note: The job is a remote job and is open to candidates in USA. Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. They are seeking a Strategic Technical Project Manager to lead complex, multi-workstream implementations within Professional Services, ensuring solutions are delivered on time and aligned to measurable impact.
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
- 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
- Mentor Senior TPMs and contribute to leadership capability within the team
Skills
- 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%
Benefits
- Commission based on performance and participation in Gainsight’s equity program
- Comprehensive benefits package including fully covered medical premiums (employee-only)
- Flexible PTO
- 401(k) plan
- Dental and vision coverage
- Remote work options
- $10,000 lifetime fertility stipend
- Access to coworking spaces around the globe
- Dedicated Recharge Holidays - one long weekend each quarter to relax and reset
- Mentoring
- Career development opportunities
Company Overview
Company H1B Sponsorship