Director, AI Solutions Delivery & Operations

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

Program Execution & Delivery Leadership

• Operationalize the enterprise AI and technology roadmap into defined workstreams, delivery sprints, milestones, resource requirements, and implementation plans.

• Lead the day-to-day AI and automation intake, feasibility assessment, business case development, and backlog prioritization process across MSP, SI, and EOR business lines.

• Direct project managers, business analysts, functional leads, and cross-functional delivery teams in moving initiatives from concept and proof-of-concept through pilot and production deployment.

• Serve as a primary delivery escalation point, identifying and removing operational blockers and resolving dependencies between business units, Product, Technology, and Operations.

• Establish disciplined delivery governance, including project status reporting, risk management, issue escalation, decision tracking, and milestone accountability.

• Partner with business and technology stakeholders to prioritize Salesforce enhancements, platform improvements, and business-critical initiatives alongside the broader AI and automation roadmap.

AI, Technology & Workflow Integration

• Partner with Technology, Engineering, Data, and Business Intelligence teams to ensure AI and automation solutions integrate effectively with core ATS, VMS, ERP, CRM, Experience Cloud, data, and operational platforms.

• Lead business requirements gathering, process discovery, functional design reviews, solution validation, user acceptance testing, and pilot rollout activities.

• Translate business challenges and operational requirements into clearly defined technical and functional requirements.

• Partner with enterprise data governance, cybersecurity, and technology teams to monitor data quality, pipeline health, model performance, system reliability, and operational uptime.

• Continuously evaluate deployed AI applications, automation workflows, and enterprise solutions to identify defects, edge cases, adoption barriers, and opportunities for improvement.

• Support the development of reusable delivery frameworks, implementation standards, and governance models for enterprise AI and automation initiatives.

Salesforce Strategy & Platform Optimization

• Serve as a strategic business owner for Salesforce, partnering with administrators, developers, implementation partners, Technology teams, and internal business stakeholders.

• Define and prioritize Salesforce business requirements, enhancement requests, platform improvements, and implementation roadmaps.

• Evaluate proposed Salesforce solution designs to ensure they align with business processes, enterprise architecture, scalability requirements, and long-term platform strategy.

• Oversee the continued evolution of Salesforce Experience Cloud and related digital experiences, including supplier-facing workflows, onboarding processes, user journeys, access models, reporting requirements, and platform usability.

• Identify opportunities to optimize Salesforce workflows, automation, integrations, data structures, and reporting capabilities to reduce manual work and improve operational visibility.

• Partner with Technology, Data, and BI teams on Salesforce integrations with enterprise platforms including Workday, Tableau, VMS platforms, data warehouses, ATS systems, and other business-critical applications.

• Support Salesforce release planning, testing, change management, deployment readiness, and post-release optimization.

• Help establish platform governance standards that balance business agility, user needs, data integrity, security, and scalability.

Operational Change Management & Adoption

• Develop and execute change management plans, user training programs, process playbooks, and standard operating procedures for new AI, automation, Salesforce, and enterprise technology solutions.

• Partner with Operations, HR, Product, and business leaders to support successful solution adoption across internal teams, clients, suppliers, and other user groups.

• Track user adoption, operational sentiment, support requirements, and friction points following deployment.

• Lead post-implementation reviews to identify lessons learned, quantify outcomes, and refine future delivery approaches.

• Support communications, testing, training, and adoption efforts associated with Salesforce enhancements and enterprise platform releases.

• Ensure new technology is embedded into business processes rather than simply deployed as standalone tools.

Performance Metrics, Value Realization & Reporting

• Maintain operational scorecards measuring portfolio delivery velocity, adoption, defect rates, SLA performance, solution utilization, and implementation effectiveness.

• Define, collect, and validate quantitative ROI measures including time savings, productivity improvements, labor efficiency gains, margin improvement, revenue impact, client savings, and risk reduction.

• Establish baseline and post-implementation measurements to determine whether initiatives are delivering expected business outcomes.

• Prepare program updates, executive reporting packages, business cases, and performance summaries for the Senior Director and executive leadership.

• Track the business impact, adoption, performance, and optimization opportunities associated with Salesforce and other enterprise technology investments.

• Use performance data and operational feedback to recommend roadmap priorities and continuous improvement opportunities.

Qualifications

Experience

• 8+ years of experience leading technology program delivery, solution design, digital transformation, enterprise applications, or technology-enabled business transformation.

• 3+ years of direct experience delivering AI, machine learning, intelligent automation, or advanced analytics initiatives preferred.

• Demonstrated experience managing complex, cross-functional technology initiatives from concept through production deployment.

• Experience working with enterprise CRM, ERP, ATS, VMS, or workforce technology platforms.

Salesforce & Enterprise Platform Experience

• Demonstrated experience translating business requirements into Salesforce or other enterprise platform solutions.

• Experience managing platform enhancement roadmaps, backlog prioritization, solution design, release readiness, and user adoption.

• Strong understanding of enterprise integrations, workflow automation, data structures, reporting, and platform governance.

• Salesforce Experience Cloud experience is strongly preferred.

• Experience partnering with Salesforce administrators, developers, architects, consulting partners, or systems integrators.

Industry & Domain Knowledge

• Direct experience within human capital management, workforce solutions, MSP, staffing, VMS, EOR, consulting, or professional services environments strongly preferred.

• Understanding of contingent workforce processes, supplier management, talent delivery, SOW/services procurement, and workforce operations is highly desirable.

Execution & Leadership

• Proven ability to lead agile delivery teams, cross-functional implementation efforts, process transformation programs, and technology adoption initiatives.

• Strong ability to move between strategic discussions and detailed operational execution.

• Demonstrated ability to manage competing priorities across multiple business units and technology platforms.

• Strong problem-solving skills with the ability to identify root causes, evaluate tradeoffs, and drive decisions.

• Ability to communicate complex technical concepts clearly to business and executive audiences.

Key Competencies

• Enterprise AI & Automation Delivery

• Salesforce Strategy & Optimization

• Digital Transformation

• Program & Portfolio Management

• Business Process Design

• Enterprise Systems Integration

• Requirements & Functional Design

• Cross-Functional Leadership

• Change Management & Adoption

• Data-Driven Decision Making

• Governance & Risk Management

• Executive Communication

• Business Value & ROI Measurement

Success in the Role

Success in this role will be measured by the ability to turn enterprise strategy into deployed solutions that are adopted by the business and produce measurable results.

The Director, AI & Enterprise Solutions will create the operational discipline required to move AI, automation, Salesforce, and enterprise technology initiatives from idea to implementation to measurable impact, while building scalable processes and platforms that support the organization’s continued growth and transformation.