Director of Enterprise, PMO

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.

Just as our employees are committed to helping our customers manage their finances, we're committed to our employees. After all, they make it happen for our customers every day.

To ensure our people can enjoy long and successful careers here at CFSI, we offer 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 be expected to 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.

Essential Responsibilities:

PMO Leadership & Strategy

• 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.

PMO Transformation & Continuous Improvement

• 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.

Portfolio & Project Governance

• 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 ensure projects remain 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.

Resource Optimization

• 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 utilizing existing resources wherever possible.
• Drive productivity improvements through workflow optimization and process redesign.Promote a culture of ownership and accountability across project teams.

Technology, Automation & AI Enablement

• Establish and maintain standards for the Bank's official project system of record (e.g., ADO or successor platform), ensuring all PMO staff create and keep complete, current project records from intake through closure.
• 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.Lead the adoption of modern project delivery technologies, automation tools, and artificial intelligence solutions.
• Identify opportunities to streamline project administration, reporting, documentation, status tracking, risk management, and stakeholder communications through technology.
• Implement scalable solutions that increase PMO capacity without requiring additional staffing.
• Introduce innovative approaches to project management, portfolio management, resource planning, and executive reporting.
• Continuously evaluate emerging technologies and best practices to improve organizational efficiency.

Risk & Issue Management

• Anticipate and identify risks, opportunities, dependencies, and costs.
• Plan resources, milestones, and deliverables to manage and implement projects.
• Escalate issues and drive problem-solving throughout the project lifecycle.
• Establish and govern standards for role definition (e.g., RACI) across all strategic initiatives, ensuring PMO staff coordinate with business and technology leaders so ownership and accountability are clearly defined before discovery begins.

Stakeholder Management

• Build trusted relationships with Executive Leadership, Business Unit Leaders, Technology teams, and Project Sponsors.
• Serve as a strategic partner to business leaders in driving enterprise change initiatives.
• Resolve project conflicts, resource constraints, and delivery risks proactively.
• Facilitate alignment among cross-functional teams and stakeholders.

Change Management & Organizational Effectiveness

• Define, communicate, and enforce phase gate and readiness criteria (e.g., dev ready checklists) so that PMO led projects meet required standards before transitioning between lifecycle stages (discovery, development, implementation).
• Lead change management efforts associated with strategic initiatives.
• Develop communication and stakeholder engagement strategies to support successful adoption of organizational change.
• Ensure project outcomes translate into measurable business value.

Ancillary Duties:

As an integral member of Project Management Office, this position is also responsible to provide assistance wherever necessary to help the Bank in achieving their annual goals.

Education/Training:

• Bachelor's degree or equivalent experience.

Skills:

• Knowledge of Project Management tools; critical thinking and problem-solving skills; planning and organizing; decision making; excellent verbal and written communication skills; ability to escalate issues; ability to delegate; team oriented; adaptability to changing environments.

Experience:

• Minimum of 5 years proven experience in leading projects, people management; strategic planning; change management and project management software. Banking experience preferred.
• All applicants must be 18 years of age or older

Compensation: Commensurate with experience plus potential for annual merit increase. In addition to your competitive salary, you will be rewarded benefits including: 11 paid holidays, paid vacation, Medical, Vision & Dental insurance, 401K with generous match, Pension, Tuition Reimbursement, Banking discounts and the list goes on!

Physical Requirements:

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. While performing the duties of this job, the employee may be required to stand, walk or sit. Use hands and fingers, handle or feel, reach with hands or arms, and speak and hear. The employee may occasionally be required to lift and or move up to 25 pounds. Specific vision abilities required by this job include close vision, and the ability to focus.

The Company is an Affirmative Action, Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, sexual orientation and gender identity), national origin, citizenship status, age, disability, genetic information, veteran status, or any other characteristic protected by applicable federal, state or local law.

The Company will make reasonable accommodations for qualified individuals with a disability. If you have a physical or mental impairment and would like to request an accommodation with respect to the application process, please contact the Human Resources Department.