Senior Director – Enterprise AI Strategy and Transformation

atPinnacle Group, Inc.Remote

Pennsylvania Full-time Artificial IntelligenceSenior

Posted 2 days ago

This is a fully remote position, open to applicants in Pennsylvania.

📋 Description

• Develop, guide, and continually enhance Pinnacle Group’s enterprise AI strategy across MSP, SI, and EOR services.

• Take ownership and execute the AI portfolio from concept through to implementation, adoption, optimization, and value realization.

• Establish processes for intake, prioritization, resource allocation, investment, and executive reporting.

• Convert corporate objectives and business needs into actionable AI programs with defined requirements, timelines, milestones, success measures, and accountable owners.

• Assess emerging AI technologies and enterprise capabilities to boost business performance, scalability, client value, and market differentiation.

• Act as an executive sponsor and thought leader for AI initiatives across the enterprise.

• Analyze applications, data environments, workflows, and business processes for opportunities in AI, automation, integration, optimization, or replacement.

• Oversee requirements gathering, design reviews, prioritization, testing, deployment, and post-implementation optimization of scalable solutions.

• Enhance enterprise analytics and AI readiness through data quality, integration, predictive insights, reporting, and performance evaluation.

• Serve as the executive AI advisor for strategic client relationships.

• Collaborate 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 change management for AI adoption, including stakeholder engagement, communications, training, readiness, adoption planning, and ongoing support.

• Set KPIs and executive reporting covering adoption, portfolio health, efficiency, productivity, revenue impact, client satisfaction, cost savings, and ROI.

• Promote collaboration, innovation, continuous learning, and responsible AI adoption throughout the enterprise.

⛳️ Requirements

• 12+ years of progressive leadership experience in staffing, workforce solutions, consulting, technology, or business transformation.

• Extensive knowledge of MSP, SI, EOR, contingent workforce programs, supplier ecosystems, VMS platforms, and workforce technologies.

• Proven experience in 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.

• Capability to translate business strategy and technical concepts into clear requirements and scalable solutions.

• Significant experience managing cross-functional initiatives, organizational change, enterprise technology adoption, executive client engagement, strategic consulting, and complex sales pursuits.

• Exceptional written and verbal communication skills for engaging with executive, client, and technical audiences.

• Knowledge of enterprise AI and generative AI platforms, workflow automation, and intelligent process automation.

• Experience with tools such as Microsoft Copilot, OpenAI, Claude, Gemini, or similar applications.

• 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.