Director of Enterprise, PMO

Overview

At Community Financial System, Inc. (CFSI), we are dedicated to providing our customers with friendly, personalized, high‑quality financial services and products. Our retail division, Community Bank, N.A., operates more than 200 customer facilities across Upstate New York, Northeastern Pennsylvania, Vermont, and Western Massachusetts. Beyond retail banking, we also offer commercial banking, wealth management, investment management, insurance and risk management, and benefit plan administration.

Our employees are committed to helping our customers manage their finances. We are equally committed to our people, ensuring long and successful careers with competitive compensation, great benefits, and professional development and advancement opportunities. As an equal‑opportunity workplace and affirmative‑action employer, we celebrate and support a diverse workplace for the benefit of all: our employees, customers, and communities.

The Head of Project Management Office (PMO) is responsible for leading and transforming the Bank’s enterprise PMO function, ensuring successful delivery of strategic initiatives across all business units. This role serves as the Bank’s central authority on project governance, portfolio management, delivery excellence, resource optimization, and organizational change management.

The successful candidate will independently lead the PMO function, establish best‑in‑class project management practices, and ensure consistent execution of strategic priorities. The individual will assess the current PMO operating model, identify gaps and inefficiencies, and implement sustainable solutions that improve project delivery outcomes without increasing headcount.

This leader will champion the use of modern technology, automation, artificial intelligence, and process innovation to increase organizational capacity, improve visibility, reduce administrative overhead, and enhance delivery performance across the Bank. The position will work closely with Executive Leadership, Technology, Operations, Business Lines, and Project Stakeholders across the organization.

• Lead and manage the Bank’s enterprise PMO function.
• Develop and execute a PMO strategy aligned with corporate objectives.
• Establish a culture of accountability, transparency, and delivery excellence.
• Serve as the primary advisor to executive leadership on project portfolio health and strategic initiative execution.
• Ensure projects are aligned with business priorities, resource capacity, and organizational goals.

• Conduct a comprehensive assessment of the existing PMO framework, operating model, methodologies, tools, governance processes, and resource utilization.
• Identify delivery gaps, inefficiencies, bottlenecks, and organizational risks.
• Develop and implement a PMO transformation roadmap.
• Introduce industry‑leading project management standards, governance structures, and delivery methodologies.
• Establish measurable KPIs and performance metrics for project delivery success.

• Define and enforce PMO practices for project initiation, ensuring project managers consistently document and obtain approval for scope, timeline, budget, and resourcing before discovery and execution begin.
• Establish governance mechanisms to keep projects on scope, schedule, budget, and strategic objectives.
• Develop executive reporting frameworks that provide meaningful insights into project performance, risks, dependencies, and resource utilization.
• Facilitate executive steering committees and project review forums.
• Utilize appropriate methodologies (Waterfall, Agile, or Hybrid) based on project objectives.
• Drive execution of project deliverables within the company’s development lifecycle standards.

• Evaluate existing PMO resources, capabilities, workload distribution, and performance.
• Recommend organizational improvements, role realignments, training opportunities, and operational enhancements.
• Develop solutions to improve PMO effectiveness using existing resources wherever possible.
• Drive productivity improvements through workflow…