Strategic Technical Project Manager

Gainsight; Tallahassee (FL); Remote; USD 150,000 - 160,000; Full time

Benefits offered by this job

Comprehensive medical coverage

Flexible PTO

401(k) plan

Fertility stipend

Access to coworking spaces

Recharge Holidays

Job summary

Gainsight is searching for a full-time Strategic Technical Project Manager to lead complex, high-visibility software projects. This remote position involves managing multi-workstream implementations and ensuring timely, on-scope delivery aligned with measurable impacts.

The ideal candidate will bring over 10 years of experience, a background in enterprise software management, and the ability to communicate effectively with both technical and executive teams. Comprehensive benefits and competitive salary are offered with performance-based commission.

Qualifications

• 10+ years of relevant experience.
• 7+ years managing software or SaaS implementations.
• Proven track record managing complex engagements.

Responsibilities

• Own accountability for multi-workstream customer engagements.
• Partner with stakeholders to define success criteria.
• Drive disciplined scope control and financial oversight.

Skills

Enterprise-grade software management

Project governance

Financial management

Stakeholder engagement

Technical fluency in APIs

Exceptional communication

Education

Bachelor's degree or equivalent experience

Job description

About This Role

We’re looking for a full-time Strategic Technical Project Manager to join our Professional Services team reporting to the Director, PMO. This remote role is based in the United States. In this role, you’ll play a key part 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.

What You'll 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.

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.

What We're 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 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%.
• Travel: Up to 15% for customer onsite engagements and company events.

Our Compensation and 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. Actual compensation may vary based on factors such as skills, experience, and location.
• We offer a 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, access to coworking spaces around the globe, and dedicated Recharge Holidays – one long weekend each quarter to relax and reset.

Legal Information

We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates.

If you require accommodations or have questions about how your personal data will be used during the hiring process, please let the recruiting team know.

If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.