Deputy Director of Technology

Center for Alternative Sentencing and Employment Services

$80K — $100K *
Information Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Bachelor's degree in Management Information Systems, Computer Science, Information Technology, or related field
  • 5+ years of experience leading an enterprise technical support team with at least 5 direct reports
  • Strong management experience in enterprise IT support operations and customer support best practices
  • Hands-on expertise with Microsoft Exchange/Microsoft 365, Active Directory, PowerShell, and endpoint management
  • Experience with cybersecurity solutions including multi-factor authentication and network security technologies
  • Proven ability to lead complex IT projects and cross-functional implementations
  • Excellent interpersonal and leadership skills, with experience in coaching and mentoring technical staff

Responsibilities

  • Plan, organize, and supervise the technical support program managing daily support needs
  • Provide support to end users and assist in staff equipment setup
  • Supervise, train, and evaluate the technical support team
  • Assign and direct staff to meet varied technology needs and priorities
  • Evaluate and recommend strategies to improve technical support services
  • Coordinate with stakeholders to address technology needs and plan for implementation
  • Collect data on technology access equity and develop plans for universal technology access

Benefits

  • Comprehensive medical, dental, and vision coverage
  • Starting at 25 days of vacation and paid time off annually, plus an additional summer self-care day
  • 12 paid holidays per year
  • Competitive retirement matching up to 6% in a 403(b) plan
  • Employee referral program
Full Job Description
Job Title:Deputy Director of Technology

Job Summary:

CASES is seeking a Deputy Director of Technology Support to lead the organization's technical support operations and ensure delivery of reliable, secure, and high-quality technology services across the agency. Reporting to the Chief Technology Officer, this role oversees the technical support team, drives service excellence, manages complex IT projects, and develops strategies that enhance end-user support, technology infrastructure, and operational efficiency.

The Deputy Director of Technology Support is a collaborative, solutions-oriented leader who excels in fast-paced environments, effectively manages competing priorities, and is passionate about building high-performing support teams, improving service delivery, and advancing technology solutions that support organizational growth and business continuity.

Salary:The salary range for this role is $80,000 - $100,000 per year

Shift Hours:This position is full-time Monday - Friday from 9:00 AM - 5:00 PM

Location Address: 4 West 125th Street, New York, N.Y. 10027. Our office is easily accessible by public transportation. You'll also be traveling to our Brooklyn and Bronx offices.

Workplace Flexibility:In-person

What You Will Be Doing:

  • Plans, organizes and supervises the technical support program; oversees daily support needs of the organization
  • Able to provide support to end users and assist with setup of staff equipment
  • Supervises, provides training and works direction to and evaluates assigned technical support team personnel
  • Assigns and directs staff to meet technology needs, priorities and timelines. Reviews and updates support assignments to assure effectiveness and balance workload
  • Evaluates level of service and effectiveness of technical support program. Recommends and implements strategies to improve support in alignment with Organization goals and site needs
  • Coordinates with stakeholders and technicians to address specific technology needs and plan for technology procurement and implementation
  • Assists with Onboarding/Off Boarding requirements and Product procurement
  • Assists in technology planning, resource prioritization and communications as an active participant of the IT management team. Needs to be the goto team leader when technicians need assistance
  • Works with stake holders to review and adjust support to meet changing needs and address gaps
  • Collects data and prepares findings related to equity of access to technology for students and staff. Develops and implements plans to fund, procure, distribute, repair and replace technology to support universal access to technology
  • Leads and participates in staff meetings to communicate objectives, share updates, collaborate and gather feedback from personnel
  • Performs other related duties as required


What We Are Looking For:

  • Bachelor's degree in Management Information Systems, Computer Science, Information Technology, or a related field
  • Five (5) or more years of experience leading an enterprise technical support team, including direct supervision of at least five staff members
  • Strong experience managing enterprise IT support operations, service delivery, and customer support best practices
  • Hands-on expertise with Microsoft Exchange/Microsoft 365 administration, Active Directory, PowerShell, endpoint/device management, and enterprise domain environments
  • Experience administering cybersecurity solutions, including email security platforms, multi-factor authentication (MFA), and network security technologies such as SonicWall firewalls and enterprise Wi-Fi environments
  • Proven ability to lead complex IT projects, technology deployments, hardware refresh initiatives, and cross-functional implementations
  • Strong troubleshooting, analytical, and problem-solving skills with the ability to serve as an escalation point for complex technical issues
  • Excellent leadership, communication, and interpersonal skills with experience coaching, mentoring, and developing technical support staff
  • Ability to prioritize competing initiatives, manage multiple projects, and thrive in a fast-paced environment
  • Must be eligible to obtain and maintain the required background clearance for CJIS data access


Additional, preferred skills we are looking for but are not required:

  • Industry certifications such as CompTIA Security+, Network+, Microsoft, Cisco, ITIL, PMP, or other relevant technical certifications
  • Experience with help desk ticketing systems and mobile device management (MDM) platforms
  • Experience managing IT vendors, contracts, procurement, and technology budgets
  • Knowledge of project management methodologies and IT service management (ITSM) best practices
  • Experience supporting organizations with multiple locations or distributed workforces


Employee Benefits:

CASES cares about employee wellbeing, and we offer a comprehensive benefits package to support you and your family, including:
  • Medical
  • Dental
  • Vision
  • Vacation and Paid Time Off - starting at 25 days off annually, Plus an additional summer selfcare day.
  • 12 Paid Holidays per year.
  • Retirement 403(b) Competitive matching up to 6%.
  • Employee Referral Program.
  • Visit www.cases.org/careers/ to learn more about benefits offered by the CASES.


Although we would love to learn about the skills of every candidate, only selected candidates that are selected will receive a response. We encourage you to apply for any position(s) you feel you are qualified for.

Monday - Friday, 9am to 5pm
35 hours per week excluding breaks

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