Strategic Technical Project Manager
Project Management
WFA Digital Insight
Gainsight's Strategic Technical Project Manager role stands out for its focus on driving the success of large-scale, high-visibility customer engagements. What makes this role particularly interesting is the opportunity to work cross-functionally with executive stakeholders, Field Delivery Engineering, Product, and Customer Success teams. Candidates should be drawn to the challenge of leading complex, multi-workstream implementations from contract signature through validated business outcomes. With a strong emphasis on strategic project leadership, executive stakeholder alignment, and disciplined scope and financial management, this role demands a unique blend of technical fluency and project governance expertise.
Job Description
We’re building the AI-driven future of customer success, from retention to growth! We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link https://www.gainsight.com.
About This Role
We’re looking for a full-time Technical Project Manager to join our Professional Services team, reporting to the SEM Manager. This role is a remote role based in the United States. In this role, you’ll play a key role in driving successful enterprise-level implementations of the Gainsight platform for our customers by owning the end-to-end onboarding and delivery lifecycle. This is a great opportunity for someone who thrives in a fast-paced, client-facing environment and enjoys working cross-functionally with teams like Sales, Customer Success, Product, and Engineering. The ideal candidate brings strong skills in enterprise project management, stakeholder communication, and enterprise software implementation.What You'll Do
- Execute complex software implementation projects while partnering closely with executive-level client sponsors to ensure alignment on scope, timeline, and desired business outcomes.
- Drive onboarding efforts for new and existing customers, prescribing best-practice recommendations that tie directly to their objectives.
- Develop and maintain detailed project plans, work breakdown structures, and communication cadences to ensure on-time, on-budget delivery.
- Track project scope and, when necessary, estimate and execute change orders in partnership with the customer.
- Produce comprehensive weekly status reports and executive communications to keep internal and external stakeholders informed.
- Proactively identify project risks and issues, developing and executing mitigation plans to maintain project health.
- Coach and mentor project team members (often across multiple time zones) to facilitate effective teamwork and knowledge transfer.
- Contribute to the continuous improvement of Professional Services by creating templates, policies, and tools that scale our delivery capabilities.
What We're Looking For
- Bachelors Degree (or equivalent experience, preferably with Project Management certification (e.g., PMP, PRINCE2) and/or 5 years of related experience - 5+ years of experience managing enterprise-grade software implementation or professional services projects, or in a related customer-facing consulting role.
- Demonstrated success leading cross-functional, geographically dispersed project teams of up to 5 members on engagements valued at $0.5M+.
- In-depth knowledge of both waterfall and agile project management methodologies and tools.
- Executive presence with highly developed communication, presentation, and stakeholder-management skills.
- Proven ability to create structure in ambiguous situations and design effective delivery processes.
- Experience working with complex, multi-divisional, multi-geographical customers.
- Up to 10-15% travel for customer onsite meetings.
- Prior experience implementing Customer Success or CRM platforms (e.g., Gainsight, Salesforce) preferred.
- Exposure to SaaS business models and metrics preferred Why You’ll Love It Here: Gainsight is a place where innovation is shaped through collaboration, curiosity, and a shared focus on solving real-world problems.
Benefits
At Gainsight, we believe great work happens when teammates feel fully supported.- The starting base salary range for this role is $70,000 – $90,000 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.
How to Stand Out
- Be prepared to showcase your experience in managing large-scale, complex projects with multiple stakeholders.
- Highlight your technical fluency, especially in areas related to APIs, data models, and enterprise integrations.
- A portfolio that demonstrates your ability to drive projects from initiation to delivery, with a focus on customer success, will be beneficial.
- Familiarize yourself with Gainsight's CustomerOS platform and its approach to AI-driven customer success to show your interest and initiative.
- During interviews, be ready to discuss how you handle change management, risk mitigation, and cross-functional team coordination.
- Prepare questions about the company culture, the role's challenges, and opportunities for professional growth to demonstrate your engagement.
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