Senior Director – Enterprise AI Strategy and Transformation

Pinnacle Group, Inc.

Senior Director shaping Pinnacle Group’s enterprise AI strategy, automation, analytics, and workforce-solutions transformation. Leading AI portfolios, governance, client advisory, adoption, and measurable business value across staffing services.

Posted 8/17/2026full-timeRemote • Pennsylvania • 🇺🇸 United StatesSeniorWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive leadership in developing and executing enterprise AI strategies, with a focus on automation, analytics, and digital transformation. Capable of translating business objectives into actionable AI programs while fostering collaboration and innovation across various organizational functions.

Highest-signal resume keywords

Enterprise AI Strategy DevelopmentCross-Functional Initiative LeadershipAI Technologies and Automation ExpertiseExecutive Client EngagementData Governance and Business Intelligence

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

AI Program ExecutionData ArchitectureApplication DevelopmentSystems IntegrationBusiness IntelligenceDigital TransformationWorkflow AutomationPredictive InsightsKPI EstablishmentChange Management

Soft Skills

Exceptional Communication SkillsRelationship BuildingOrganizational Change ManagementStrategic Problem SolvingResults Orientation

Tools & Technologies

Microsoft CopilotOpenAIClaudeGeminiPower BITableauSalesforceServiceNowFreshServiceVMS Technologies

Industry Keywords

MSPSIEORContingent Workforce ProgramsSupplier EcosystemsVMS PlatformsWorkforce TechnologiesEnterprise AIGenerative AIIntelligent Process Automation

Tech Stack

Tools & technologies

ServiceNowTableau

About the role

Key responsibilities & impact

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

What you’ll need

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

Benefits

Comp & perks

🌐 Worldwide ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs ✉️ Email Alerts 👤 Account Pinnacle Group, Inc. Website LinkedIn All 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. Senior Director – Enterprise AI Strategy and Transformation 🔥 1 minute ago 🔔 Pennsylvania – Remote ⏰ Full Time 🟠 Senior 🤖 Artificial Intelligence Apply Now Customize resume + cover letter Report problem ☆ Save ☑️ Mark as applied ❌ Hide 📋 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 Apply Now 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score Similar Jobs AI Standards Engineer 🔥 16 minutes ago Guidehouse 10,000+ employees 🏥 Healthcare 🎖️ Defense 📦 Logistics Website LinkedIn All Job Openings AI standards engineer governing secure Databricks AI/ML development at Guidehouse. Establishing model lifecycle, MLOps, governance, compliance, and quality standards for government and enterprise programs. 🇺🇸 United States – Remote 💵 $85k - $141k / year 💰 Grant on 2023-02 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤖 Artificial Intelligence 🦅 H1B Visa Sponsor Manager, AI Operations 🔥 33 minutes ago Xsolis 201 - 500 🏥 Healthcare ☁️ SaaS 🤖 Artificial Intelligence Website LinkedIn All Job Openings AI Operations Manager ensuring reliable, observable, and secure traditional ML, GenAI, and agentic systems. Advancing ethical AI operations for Xsolis’s healthcare technology platform. 🇺🇸 United States – Remote 💰 $75M Private Equity Round - Xsolis on 2021-06 ⏰ Full Time 🟠 Senior 🔴 Lead 🤖 Artificial Intelligence Project Specialist – AI/AN Victim Services Programs 🔥 1 hour ago ICF 5001 - 10000 🏥 Healthcare 📦 Logistics 📣 Marketing Website LinkedIn All Job Openings ICF project specialist supporting Alaska Native victim services programs through culturally responsive training, grant compliance, and strategic planning. Remote Alaska role serving communities and federal government clients. 🇺🇸 United States – Remote 💵 $61k - $103.6k / year 💰 $30M Grant on 2021-03 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤖 Artificial Intelligence 🦅 H1B Visa Sponsor AI Ops Engineer 🔥 2 hours ago Endava 10,000+ employees 🏥 Healthcare 📣 Marketing 📦 Logistics Website LinkedIn All Job Openings AI Ops Engineer building LLM agents and RAG workflows for Endava’s enterprise infrastructure platform. Integrating ServiceNow, Dynatrace, Zabbix, and GCP for intelligent operations. 🇺🇸 United States – Remote 💰 Post-IPO Debt on 2023-02 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤖 Artificial Intelligence Manager, AI Agents and Automation 🔥 5 hours ago Jerry 201 - 500 💼 Consulting 📦 Logistics 📣 Marketing Website LinkedIn All Job Openings AI platform manager building agentic AI products for Jerry.ai, which manages car and home ownership. Leading LLM workflows, automation, experimentation, and OpenAI partnerships. 🇺🇸 United States – Remote 💵 $130k - $170k / year ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤖 Artificial Intelligence 🦅 H1B Visa Sponsor View More Artificial Intelligence Jobs 🌐 Worldwide Built by Lior Neu-ner. I'd love to hear your feedback — Get in touch via DM or support@remoterocketship.com Search Search Jobs by country Search jobs by city Search jobs by job title Search entry-level jobs Search junior-level jobs Search senior-level jobs Search jobs by tech stack Search jobs by contract type Search remote internships Search remote part-time jobs Remote jobs Anywhere in the World Companies Hiring Anywhere in the World Companies Hiring Sales People Anywhere in the World Companies Hiring Software Engineers Anywhere in the World Resources Advice Tips for finding remote jobs Interview questions and answers Resume examples Cover letter examples Post a job Affiliates About us Is Remote Rocketship legit? Privacy policy Terms of service Job board SEO course Remote Job Search MasterClass Resume Review AI Apply Copilot OpenClaw job finder Find jobs using your resume Jobs by Country Remote jobs anywhere in the world (Worldwide remote jobs) Remote jobs United States Remote jobs Australia Remote jobs Brazil Remote jobs Canada Remote jobs France Remote jobs Ireland Remote jobs Germany Remote jobs Netherlands Remote jobs Spain Remote jobs UK Popular Jobs Remote data analyst jobs Remote customer support jobs Remote executive assistant jobs Remote marketing jobs Remote product designer jobs Remote product manager jobs Remote project manager jobs Remote recruiter jobs Remote sales jobs Remote software engineer jobs Jobs by Type Remote full-time jobs Remote part-time jobs Remote contract jobs Remote internship jobs Remote entry-level jobs Remote jobs with no experience required Remote junior jobs (1-3 years of experience) Digital nomad jobs Remote jobs with no degree required Freelance remote jobs Temporary remote jobs Remote jobs hiring now Stay at home mom jobs