Sr Director of Technology

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 Senior Director of Technology is responsible for driving the strategic direction, operational excellence, and innovation within the organization's core technology infrastructure. This role has direct ownership of data center operations, enterprise IT data center strategy, and technology service delivery across the organization. The Senior Director will provide leadership for the Director of Technology Services and Director of Business Applications, ensuring cohesive alignment between infrastructure and business applications.

Key Responsibilities:

Strategic Technology Leadership

• Develop and execute a comprehensive IT operations and infastructure strategy aligned with enterprise objectives.
• Serve as a key advisor to the CTO, contributing to the long-term vision for technological growth and innovation.
• Lead data center modernization efforts, ensuring high availability, scalability, and cost-efficiency.
• Champion digital transformation initiatives that enhance service delivery and enterprise agility.

Operational Oversight

• Own the performance, security, and continuity of the Bank's technology infrastructure and IT operations including segmentation where practical.

• Direct and optimize support models to ensure a responsive and high-performing service desk and operations team.
• Ensure that enterprise applications and infrastructure meet or exceed SLA and compliance requirements.
• Continuously assess and enhance ITIL-based processes for incident, problem, change, and configuration management.
• Oversee the development, testing, and maintenance of IT Disaster Recovery (DR) plans to ensure minimal disruption and rapid recovery of critical systems.
• Support enterprise Business Continuity Planning (BCP) by ensuring infrastructure and applications can meet recovery objectives during operational disruptions.

Leadership and Talent Development

• Provide leadership, coaching and development to the Director of Technology Services and Director of Business Applications.
• Create a culture of innovation and continuous improvement across the IT department.
• Identify future talent needs and build a robust succession pipeline for critical technology roles.

Security and Compliance

• Partner with the Chief Information Security Officer (CISO) and internal audit teams to maintain a strong cyber risk posture.
• Support regulatory compliance efforts and actively participate in audit and examination processes.
• When requested, represent the Technology organization in Audit and Risk Committee meetings to report on outstanding audit findings, outline remediation plans, and demonstrate ongoing risk mitigation progress.

Innovation and Architecture

• Stay abreast of emperging technologies and trends, especially in cloud computing, automation, and data center technologies/operations.
• Lead architectural planning and the adoption of cloud-first, hybrid, and virtualization strategies with a focus on Azure.
• Ensure IT systems are adaptable, resilient, and aligned with evolving business requirements.

Governance and Vendor Management

• Lead IT Sub-Committee meetings and contribute actively to IT Steering Committee initiatives.
• Oversee contracts and vendor relationships related to infrastructure, cloud, support, and software systems.

Education:

• Bachelor's degree in Information Technology, Computer Science, Information Systems, or related field required. Master's degree preferred.
• Experience: Minimum of 10 years of progressive experience in IT leadership, including at least 3 years in a senior management or strategic oversight role.
• Certifications (preferred): ITIL, PMP, Azure certifications, or similar relevant industry credentials.
• Skills and Attributes:
  • Visionary leadership with a strong technical foundation
  • Proven success in leading large IT teams across infrastructure and application domains
  • Strong analytical, communication, and interpersonal skills
  • Deep expertise in Microsoft Azure, virtualization (Citrix, Azure, Nutanix), Exchange, and modern IT compute and network architecture
  • Demonstrated ability to lead cross-functional initiatives and manage vendor relationships
  • High level of integrity and a customer-centric mindset
• Other: Valid driver's license. Position requires up to 15% travel to remote office locations.
• All applicants must be 18 years of age or older
• Maintain proficient knowledge of, and demonstrate ongoing compliance with all laws and regulations applicable to this position, ensure ongoing adherence to policies, procedures, and internal controls, and meet all training requirements in a timely manner

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.