Strategic Technical Project Manager

Role Description

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 the success of large-scale, high-visibility customer engagements within Professional Services by leading complex, multi-workstream implementations from contract signature through validated business outcomes. You’ll ensure solutions are delivered on time, within scope, and aligned to measurable impact by owning end-to-end engagement governance, aligning executive stakeholders, and orchestrating cross-functional execution across Sales, Customer Success, Solution Architecture, Product, and Engineering.

This is a great opportunity for someone who thrives in fast-paced, evolving product environments and enjoys working cross-functionally with executive stakeholders, Field Delivery Engineering (FDE), Product, Engineering, and Customer Success teams. The ideal candidate brings strong skills in strategic project leadership, executive stakeholder alignment, and disciplined scope and financial management, along with the technical fluency needed to guide architectural discussions and proactively mitigate delivery risk.

What You'll 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.
• Mentor Senior TPMs and contribute to leadership capability within the team.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. This role will require occasional travel for team meetings, training, or company events.

Qualifications

• 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

• The starting base salary range for this role is $150,000 – $160,000 USD annually.
• This role is also eligible for 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, 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.