The Lead Project Manager provides strategic leadership for the most complex enterprise programs and portfolios, driving Agile delivery at scale and championing AI-first project management practices. This role sets the vision for Agile and agentic AI adoption across the IT Project Management function, governs cross-portfolio dependencies, and mentors the full PM team. The Lead Project Manager partners with enterprise architecture, data, and AI governance teams to define and operationalize AI-enabled project delivery capabilities, ensuring alignment with organizational standards. Additionally, this role ensures strong alignment between technology investments and business strategy while advancing enterprise-wide delivery maturity.
PRINCIPAL RESPONSIBILITIES AND DUTIES:
- 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.
- Leads 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.
- Other duties as needed or required.
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.
APPLICATION PROCESS:
You can directly apply through Cass's website at https://www.cassinfo.com/careers. Please apply directly to this position via the “Apply” button. You will be required to create an account and provide your resume, contact information and other pertinent employment information. This process typically takes 20 minutes or less. Should we find that you meet the minimum requirement of the position, a member of our recruiting team will be in touch to start the interview process.
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 $2.4 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 was recently named as one of America’s best midsize companies by a leading publication and is part of the Russell 2000®. More information is available at www.cassinfo.com.
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