Lead Project Manager

Principals

• Sets strategic portfolio vision, investment themes, and value delivery roadmaps in collaboration with executive leadership and enterprise stakeholders across business and IT.
• Accountable for portfolio-level governance, Agile program delivery, and continuous value realization across all phases of the delivery lifecycle.
• Develops portfolio-level strategies, executive communication frameworks, and AI-enhanced program dashboards for enterprise visibility.
• Provides executive-level communication of portfolio health, strategic delivery risks, and AI-driven program insights to C-suite and board stakeholders.
• Ensures enterprise programs deliver measurable business value through Agile delivery, continuous feedback loops, and AI-optimized resource allocation.
• Governs strategic vendor and partner ecosystems, negotiating Agile delivery contracts and ensuring AI-readiness across the vendor landscape.
• Leads enterprise resource strategy, championing self-organizing teams and optimizing talent allocation across the Agile portfolio.
• Architects enterprise dependency management strategies, using AI-powered tools to visualize and resolve cross-portfolio risks.
• Orchestrates enterprise PI Planning, portfolio Kanban, and strategic milestone management using AI-enhanced enterprise Agile platforms.
• Defines and monitors portfolio-level KPIs, value stream metrics, and AI-generated predictive delivery indicators.
• Develops and presents executive portfolio reviews, AI-powered forecasting reports, and strategic investment recommendations.
• Led enterprise risk governance, leveraging AI-driven scenario modeling and predictive risk analytics to guide strategic decisions.
• Defines portfolio success frameworks, OKRs, and value realization metrics, ensuring strategic alignment across the enterprise.
• Leads enterprise Inspect and Adapt cycles, drives organizational learning culture, and commissions AI-assisted trend analysis for strategic improvement.
• Establishes enterprise Agile governance standards, AI-augmented delivery playbooks, and centers of excellence for project management.
• Governs enterprise risk frameworks using AI-powered risk intelligence, maintaining strategic risk portfolios and driving rapid executive response.
• Defines enterprise-wide Agile metrics frameworks, AI-assisted estimation models, and standardized delivery measurement systems for portfolio governance.
• Oversees the enterprise project portfolio including programs, ensuring Agile value delivery and AI-optimized financial management.
• Manages complex multi-vendor projects which contain multiple streams (requirements, development, quality assurance).
• PARTNERS WITH EXECUTIVE BUSINESS OWNERS TO DRIVE DIGITAL TRANSFORMATION, MINIMIZE OPERATIONAL DISRUPTION, AND MAXIMIZE AI-DRIVEN OPERATIONAL EFFICIENCY.
• SERVES AS THE AGILE AND AI CHAMPION FOR THE IT PM FUNCTION, MENTORING ALL LEVELS OF PROJECT MANAGERS ON AGILE LEADERSHIP, AI ADOPTION, AND PROFESSIONAL GROWTH.

Skills and Abilities Required

• Mastery of enterprise Agile and portfolio management platforms (e.g., Azure Dev Ops) with strategic oversight of toolchain selection and governance.
• Expert in executive communication platforms, AI-powered analytics suites, and enterprise collaboration ecosystems.
• Expert in enterprise architecture tools, value stream mapping, and AI-powered modeling platforms for strategic planning.
• Advanced data and analytics literacy, including experience governing AI/ML pipelines, data strategy, and analytics-driven portfolio decisions.
• Deep technical breadth across enterprise platforms, AI technologies, cloud ecosystems, and digital transformation tools.
• Ability to work both independently and in a team-oriented, collaborative environment.
• Executive-level strategic thinking with the ability to navigate organizational complexity, drive transformation, and make data-driven decisions under uncertainty.
• Executive influence and stakeholder management skills, with demonstrated ability to align C-suite leaders, board members, and enterprise partners.
• Organizational savvy with the ability to drive enterprise change through executive relationships, political acumen, and strategic communication.
• Strong written and oral communication skills.
• Strong interpersonal skills.
• Industry thought leadership in Agile delivery, AI-augmented project management, and emerging technology trends.
• Customer service skills.
• Ability to effectively prioritize and execute tasks in a high-pressure environment.

Minimum Level of Preparation and Training Normally Required

• A bachelor’s degree in computer science or business administration with an emphasis in management information systems or equivalent work experience.
• 7+ years of progressive project management experience, including 5+ years leading enterprise Agile programs and AI-augmented delivery initiatives.
• PMP and SAFe Program Consultant (SPC) or SAFe Fellow certification required. Additional certifications in AI, Lean Portfolio Management, or enterprise Agile strongly preferred.
• Evaluates, selects, and oversees implementation of enterprise AI platforms for project portfolio management, resource optimization, and predictive delivery analytics.
• Leads Agile Center of Excellence initiatives, establishing training programs, certification pathways, and maturity assessments across the organization.
• Strategic expertise in agentic AI, including AI governance, enterprise AI platform evaluation, prompt engineering strategy, and building AI-first PM organizations.
• Mastery of Agile at scale (SAFe, LeSS, Disciplined Agile) with experience leading enterprise-level Agile transformations.
• Experience presenting to executive leadership and governing enterprise technology investments.

About Our Company

Cass Information Systems, Inc. (NASDAQ: CASS) is a leading provider of integrated information and payment management solutions. Cass enables enterprises to achieve visibility, control, and efficiency in their supply chains, communication networks, facilities, and other operations. Disbursing over $94 billion annually on behalf of its clients, and with total assets of $2.5 billion, Cass is uniquely supported by Cass Commercial Bank. Founded in 1906 and a wholly-owned subsidiary, Cass Commercial Bank provides sophisticated financial exchange services to the parent organization and its clients. Cass is part of the Russell 2000®. More information is available at www.cassinfo.com.