Director Of Information Technology

The United States Probation Office for the District of Connecticut is seeking a highly skilled and forward-thinking Director of Information Technology to lead the Department’s technology strategy, operations, security, and modernization efforts. This is a succession-based leadership position: the successful candidate will initially work under the current IT Department Head until his planned retirement in September 2026. Upon satisfactory performance, the successful candidate will assume full responsibility of the IT Department as Director of Information Technology.

The Director oversees all department-wide IT functions, supervises IT staff, and plays a central role in the Probation’s strategic adoption of artificial intelligence (AI) and automation technologies. The position requires strong technical expertise—including programming skills—as well as proven leadership, communication, and project management abilities.

This position may also serve as the Department’s Contracting Officer, responsible for IT related procurement, vendor management, and compliance with judiciary contracting rules.

Representative Duties
Leadership & Management
Provide strategic leadership, long-term planning, and operational oversight for all IT functions across multiple divisional offices. Supervise, mentor, and develop IT staff; set priorities, assign work, evaluate performance, and foster a collaborative, service-oriented environment. Serve as the Department’s principal advisor on emerging technologies, cybersecurity threats, and modernization opportunities. Work closely with other Court departments and Probation Offices, senior management, and national judiciary partners to align technology initiatives with operational needs.

Technology Operations, IT Security
Oversee the operation, maintenance, and security of mission-critical systems, including PACTS 360, Officer/field technology, VOIP, conference platforms, and internal applications. Ensure compliance with judiciary IT policies, security protocols, audit requirements, and national standards. Manage IT disaster recovery planning, continuity of operations (COOP), and incident response. Maintain and enhance the Court’s network, desktops, laptops, servers, A/V systems, virtualization platforms, and telecommunications systems.

AI, Automation, and Innovation
Lead the Court’s exploration, evaluation, and implementation of AI-driven tools to improve efficiency and reduce administrative burden. Identify opportunities for automation in document analysis, data extraction, scheduling, and knowledge management. Ensure all AI use complies with judiciary guidance, privacy protections, and ethical standards.

Programming & Technical Development
Utilize programming skills to support local application development, data integration, automation scripts, and system customization. Evaluate and adapt national systems to meet local needs; design or modify tools to support Department operations. Maintain documentation, code repositories, and technical standards for locally developed solutions.

Budgeting, Procurement & Contracting
Develop and manage the IT budget, lifecycle planning, and procurement of hardware, software, and services. Serve as the Department’s Contracting Officer (IT specific), ensuring compliance with judiciary procurement rules and managing vendor relationships.

Qualifications
Required Qualifications
Bachelor’s degree in information technology, computer science, management, or a related field. At least six years of progressively responsible IT experience, including three years in a supervisory or management role. Demonstrated expertise in network administration, cybersecurity, enterprise systems, IT security auditing, and IT project management. Programming experience in one or more languages (e.g., Python, PowerShell, JavaScript, SQL, or similar and familiarity with REST API). Strong leadership, communication, and team-building skills. Ability to work collaboratively with judges, executives, and staff at all levels.

Preferred Qualifications
Experience in a federal court, government agency, or similarly regulated environment. Familiarity with CM/ECF, courtroom technology, and judiciary IT policies. Background in evaluating or implementing AI, machine learning, or automation tools. Experience managing budgets, procurement, and vendor relationships. Certifications such as CISSP, PMP, ITIL, or equivalent. Microsoft (MS) Windows Server (2022 and above), Windows 11, MS Windows Active Directory with server administration (including Group Policy), Microsoft 365, Drupal, Sharepoint Online, virtualization hosting software (VMWare), Cisco switches and wireless access points, the Qualys suite of security tools, Microsoft Power Automate, and Power Apps.

Personal Attributes
The ideal candidate will be a strategic thinker who balances innovation with security, compliance, and practicality. A proactive leader who anticipates technological needs and communicates effectively with non-technical stakeholders. A steady, collaborative partner capable of guiding the Department through modernization while maintaining operational stability. The candidate will be hands-on while maintaining big-picture perspective.

Conditions of Employment
Employees of the United States Probation & Pretrial Services Office serve under “Excepted Appointment” and are considered “At-Will” and can be terminated with or without cause by the court. Employees are required to adhere to the Code of Conduct for Judicial Employees. Applicants must be U.S. citizens or otherwise eligible to work in the United States. As a condition of employment, the selected candidate is required to undergo a high-sensitive background check as a condition of employment. All appointments are subject to mandatory electronic funds transfer for payment of net pay.

Employee Benefits
Court employees are considered at‐will and are not covered by federal civil service rules. They are, however, entitled to the same benefits as other federal employees. These include:
• Accrual of paid vacation and sick leave, based on length of service
• 11 paid holidays per year
• Federal Employees Health, Dental and Vision Insurance Programs with generous government contribution to the health insurance premium
• Federal Employees’ Group Life Insurance
• Pension/Federal Employees Retirement System (FERS)
• Thrift Savings Plan (TSP) with employer matching contributions
• Long-Term Care Insurance Program
• Flexible Spending Accounts Program
• Telework and flexible work schedule may be possible with the approval of the Chief Probation Officer
Please visit https://www.uscourts.gov/careers/benefits for additional information on benefits.

Application Process
Applicants must submit ONE PDF containing:
• A cover letter describing relevant experience, leadership approach, and interest in the position.
• A résumé detailing education, work history, programming experience, and accomplishments.
• Contact information for three professional references.
• A completed AO-78 Application for Judicial Branch Federal Employment. (http://www.uscourts.gov/uscourts/FormsAndFees/Forms/AO078.pdf)
Submit application materials to: HR_Department@ctd.uscourts.gov (please include #26-02 in the subject line).
Only the most qualified applicants will be contacted for interviews. The court reserves the right to amend or withdraw this vacancy announcement with or without written notice to applicants.
U.S. Probation & Pretrial Services is an Equal Opportunity Employer.