Senior Director - Enterprise AI Strategy and Transformation

Pinnacle Group exists to connect people with opportunity. For the last 25 years, we've done exactly that by living our core values of putting people first, delivering excellence in all we do, and giving back to the communities in which we live and work. We are a leading workforce solutions company supporting the talent needs of global leaders in financial services, technology, communications, utilities, and transportation and we are one of the largest women and minority-owned companies in our industry. Our team of service-driven, energetic, and diverse professionals is well-respected in our industry and our leadership team is aligned and focused on taking the company to the next level. If you're looking for a new opportunity where you can truly make a difference, we hope you'll apply for a position with us. Job Summary Areas of Responsibility Enterprise AI Strategy, Roadmap & Portfolio Leadership Develop, lead, and continuously evolve Pinnacle Group's enterprise AI strategy across Strategic Services (MSP, SI, and EOR) including internal, supplier, client, and operational roadmaps. Own and execute Strategic Services' 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 identify opportunities that improve business performance, scalability, client value, and market differentiation. Serve as executive sponsor and enterprise thought leader for AI initiatives while setting standards and best practices for responsible, secure, and scalable adoption. Solution Delivery, Applications, Data & Process Optimization Evaluate existing applications, data environments, workflows, and business processes to identify opportunities for AI, automation, integration, optimization, or replacement. Determine when existing platforms should be enhanced versus when proprietary AI-enabled applications, intelligent workflows, or automation capabilities should be developed to improve service delivery, productivity, user experience, and cost efficiency. Partner with Technology, Product, Engineering, Business Intelligence, Operations, and other functions to translate business needs into scalable solutions; lead requirements, design reviews, prioritization, testing, deployment, and post-implementation optimization. Ensure solutions are built and applied correctly, align with business objectives, enterprise architecture, security and data standards, and leverage trusted, accessible, governed, and compliant data environments. Advance enterprise analytics and AI readiness through improved data quality, integration, predictive insights, reporting, and continuous evaluation of application performance, adoption, and ROI. Client Engagement, Commercial Enablement & Enterprise Collaboration Serve as Pinnacle's executive AI advisor for strategic client relationships, leading discussions on AI strategy, workforce transformation, automation, analytics, and digital innovation. Partner with Sales, Business Development, Account Management, and Solutions on strategic pursuits, RFPs, executive presentations, solution design, QBRs, client workshops, and innovation sessions. Identify opportunities to expand client relationships and create repeatable AI-enabled offerings, consulting capabilities, and new revenue opportunities. Build strong partnerships across Strategic Services (MSP, SI, EOR) Technology, Product, Operations, Sales, Marketing, HR, Finance, Legal, and Executive Leadership; influence priorities through clear communication, teamwork, executive presence, and relationship management. Provide strategic direction and mentorship to the AI & Automation Strategy function and represent Pinnacle in executive client meetings, strategic partnerships, industry events, and thought leadership opportunities as appropriate. Governance, Change Management & Value Realization Establish governance, in coordination with corporate IT, GRC, and APS teams, for responsible AI development, deployment, and adoption, including policies and operating standards for data privacy, security, regulatory compliance, risk management, and client-specific requirements. Partner with Legal, Compliance, Information Security, Technology, and Executive Leadership to ensure AI initiatives meet internal and external requirements and are appropriately governed throughout the lifecycle. Ensure AI solutions used by Pinnacle Group comply at all times with internal policies, client policies, and applicable regulations. Lead change management for AI adoption, including stakeholder engagement, communications, training, readiness, adoption planning, and ongoing support for employees, clients, suppliers, and business partners. Establish KPIs and executive reporting that measure AI adoption, portfolio health, operational efficiency, productivity, revenue impact, client satisfaction, cost savings, and ROI; use results to guide future investment and optimization. Foster a culture of collaboration, innovation, continuous learning, and responsible AI adoption across the enterprise. Qualifications Experience & Technical Knowledge 12+ years of progressive leadership experience within staffing, workforce solutions, consulting, technology, or business transformation, with deep knowledge of MSP, SI, EOR, contingent workforce programs, supplier ecosystems, VMS platforms, and workforce technologies. Demonstrated experience leading enterprise AI, automation, analytics, and digital transformation initiatives from strategy through execution, including evaluation of business processes and technology platforms for optimization and AI-enabled innovation. Deep understanding of enterprise data environments, data governance, business intelligence, automation, AI technologies, data architecture, application development, systems integration, and product delivery methodologies. Proven ability to translate business strategy and technical concepts into clear requirements and scalable solutions while partnering effectively with technical development teams and executive stakeholders. Significant experience leading complex cross-functional initiatives, organizational change, enterprise technology adoption, executive client engagement, strategic consulting, and complex sales pursuits. Exceptional written and verbal communication skills, with the ability to clearly convey business requirements, technical concepts, risks, opportunities, and recommendations to executive, client, and technical audiences. Strong knowledge of enterprise AI and generative AI platforms, workflow and intelligent process automation; experience with Microsoft Copilot, OpenAI, Claude, Gemini or comparable tools, and familiarity with Power BI, Tableau, Salesforce, ServiceNow, FreshService, VMS technologies, and enterprise workflow applications. Qualifications Leadership Competencies Enterprise Strategic Leadership Executive Presence Workforce Solutions Expertise AI & Digital Transformation Leadership Data & Business Intelligence Acumen Executive Client Engagement Commercial & Financial Acumen Cross-Functional Collaboration Exceptional Communication Relationship Building & Influence Organizational Change Management Innovation & Continuous Improvement Strategic Problem Solving Results Orientation Success Measures Successful execution of Pinnacle Group's enterprise AI strategy and roadmap with measurable business outcomes and strong cross-functional alignment. Quantifiable operational efficiency, productivity improvement, workflow automation, and cost savings resulting from AI initiatives and application optimization. Successful implementation and adoption of AI solutions across employees, suppliers, and clients, supported by effective governance and change management. Development of scalable, repeatable AI-enabled applications, capabilities, and offerings that improve service delivery and create competitive differentiation. Increased client engagement, retention, sales effectiveness, and revenue opportunities driven by AI innovation and executive advisory support. Recognition of Pinnacle Group as an innovative, responsible, AI-enabled leader within the workforce solutions industry.