Senior Director – Enterprise AI Strategy and Transformation

🔥 0 minutes ago

🔔 Pennsylvania – Remote

🔔 Pennsylvania – Remote

⏰ Full Time

🟠 Senior

🤖 Artificial Intelligence

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Pinnacle Group, Inc.

WebsiteLinkedInAll Job Openings

5001 - 10000 employees

🏢 Enterprise

👥 HR Tech

🤝 B2B

Enterprise • HR Tech • B2B

Pinnacle Group, Inc. is a leading provider of contingent workforce solutions, specializing in Managed Services (MSP), Vendor Management Software (VMS) implementation, and payrolling services. As a diversity-driven, VMS-agnostic service provider, Pinnacle Group delivers scalable workforce solutions globally, ensuring cost savings, attrition reduction, and compliance for its clients. With a strong focus on strategic services, Pinnacle has partnered with Fortune 500 companies to optimize their workforce management, achieving 100% supplier payment accuracy. The company is Latina-owned and is recognized for its commitment to supplier diversity and innovative workforce strategies.

📋 Description

• Develop, lead, and continuously evolve Pinnacle Group’s enterprise AI strategy across MSP, SI, and EOR services • Own and execute the AI portfolio from concept through implementation, adoption, optimization, and value realization • Establish intake, prioritization, resource allocation, investment, and executive reporting processes • Translate corporate objectives and business needs into executable AI programs with defined requirements, timelines, milestones, success measures, and accountable owners • Evaluate emerging AI technologies and enterprise capabilities to improve business performance, scalability, client value, and market differentiation • Serve as executive sponsor and enterprise thought leader for AI initiatives • Evaluate applications, data environments, workflows, and business processes for AI, automation, integration, optimization, or replacement opportunities • Lead requirements, design reviews, prioritization, testing, deployment, and post-implementation optimization of scalable solutions • Advance enterprise analytics and AI readiness through data quality, integration, predictive insights, reporting, and performance evaluation • Serve as executive AI advisor for strategic client relationships • Partner on strategic pursuits, RFPs, executive presentations, solution design, QBRs, client workshops, and innovation sessions • Identify repeatable AI-enabled offerings, consulting capabilities, and new revenue opportunities • Build partnerships across Strategic Services, Technology, Product, Operations, Sales, Marketing, HR, Finance, Legal, and Executive Leadership • Provide strategic direction and mentorship to the AI & Automation Strategy function • Establish governance for responsible AI development, deployment, and adoption • Lead AI adoption change management, including stakeholder engagement, communications, training, readiness, adoption planning, and ongoing support • Establish KPIs and executive reporting covering adoption, portfolio health, efficiency, productivity, revenue impact, client satisfaction, cost savings, and ROI • Foster collaboration, innovation, continuous learning, and responsible AI adoption across the enterprise

🎯 Requirements

• 12+ years of progressive leadership experience in staffing, workforce solutions, consulting, technology, or business transformation • Deep knowledge of MSP, SI, EOR, contingent workforce programs, supplier ecosystems, VMS platforms, and workforce technologies • Experience leading enterprise AI, automation, analytics, and digital transformation initiatives from strategy through execution • Understanding of enterprise data environments, data governance, business intelligence, automation, AI technologies, data architecture, application development, systems integration, and product delivery methodologies • Ability to translate business strategy and technical concepts into clear requirements and scalable solutions • Significant experience leading cross-functional initiatives, organizational change, enterprise technology adoption, executive client engagement, strategic consulting, and complex sales pursuits • Exceptional written and verbal communication skills for executive, client, and technical audiences • Knowledge of enterprise AI and generative AI platforms, workflow automation, and intelligent process automation • Experience with Microsoft Copilot, OpenAI, Claude, Gemini, or comparable tools • Familiarity with Power BI, Tableau, Salesforce, ServiceNow, FreshService, VMS technologies, and enterprise workflow applications • Leadership competencies including executive strategic leadership, executive presence, workforce solutions expertise, AI and digital transformation leadership, data and business intelligence acumen, executive client engagement, commercial and financial acumen, cross-functional collaboration, communication, relationship building, organizational change management, innovation, strategic problem solving, and results orientation