Strategic Technical Project Manager, AI Deployments

🕒 July 28

🐊 Florida – Remote

🐊 Florida – Remote

💵 $150k - $160k / year

⏰ Full Time

🟠 Senior

🔴 Lead

🤓 Technical Project Manager

👻 Ghost score 43%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Gainsight

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

☁️ SaaS

🤝 B2B

🏢 Enterprise

💰 $52M Series E - Gainsight on 2017-05

SaaS • B2B • Enterprise

Gainsight is a SaaS company that provides a unified Customer Success platform and related products to help businesses retain, expand, and drive product adoption with their customers. Its offerings include Gainsight CS (customer success), Product Experience (in-app engagements and analytics), Customer Communities, Skilljar (customer education), and AI-powered agents and services (Staircase AI, Agent Studio, Gainsight MCP) that surface insights and automate customer success workflows. Gainsight positions itself as an enterprise-focused, AI-native solution for post-sales teams, emphasizing retention-as-a-service, integrated customer data, and scalability for CSMs and product teams.

📋 Description

• 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 and deployable workflows • Create and manage parallel technical implementation workstreams, including AI platform configuration, integrations, system access, AI agent workflows, and reporting builds • Oversee human agent readiness plans, including staffing timelines, onboarding and training schedules, and certifications • 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 scope control, change management, and financial oversight • Coordinate Solution Architecture, Customer Success, Product, and Engineering teams • Identify and mitigate technical, operational, and organizational risks • Partner with technical teams to ensure solutions are architecturally sound without serving as the primary engineer • Monitor post-deployment performance and drive follow-up actions to improve adoption, stability, trust, and measurable business outcomes • Mentor Senior TPMs and contribute to team leadership capability • Report to the Director, PMO

🎯 Requirements

• Bachelor’s degree in Computer Science, Engineering, or a related technical field (or equivalent experience) • 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% • Preferred: experience in a Field Delivery Engineering (FDE) or customer-embedded delivery model • Preferred: experience with business process outsourcing projects • Preferred: experience implementing Customer Success, CRM, or enterprise SaaS platforms • Preferred: familiarity with AI-driven solutions, automation, or advanced analytics implementations • Preferred: Project Management certification (PMP, PRINCE2, or equivalent)

🏖️ Benefits

• Commission based on performance • Participation in Gainsight’s equity program • 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 • Recharge Holidays — one long weekend each quarter • Mentoring and career development opportunities • Occasional travel for team meetings, training, or company events