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Contractual Cyber Security Apprenticeship Jobs (NOW HIRING)

CESA 6

Manager, IT

Oshkosh, WI

$85K - $100K/yr

The Manager oversees one Senior Support Specialist and one Youth Apprenticeship Intern and reports ... Oversee IT risk management practices, including cybersecurity, system access and permissions ...

M.C. Dean, Inc

Electrical QC Inspector Supervisor

Aldie, VA · On-site

$90K - $113K/yr

... and cybersecurity industries. The Electrical QC Supervisor provides day-to-day leadership of ... Make day-to-day operational quality decisions; elevate high-risk or contractual issues to project ...

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How much do contractual cyber security apprenticeship jobs pay per year?

As of Sep 2, 2026, the average yearly pay for contractual cyber security apprenticeship in the United States is $132,962.00, according to ZipRecruiter salary data. Most workers in this role earn between $111,000.00 and $150,000.00 per year, depending on experience, location, and employer.
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Infographic showing various Contractual Cyber Security Apprenticeship job openings in the United States as of August 2026, with employment types broken down into 86% Full Time, 12% Part Time, and 2% Contract. Highlights an 91% Physical, 2% Hybrid, and 7% Remote job distribution, with an average salary of $132,962 per year, or $63.9 per hour.

Manager, IT

Cooperative Educational Service Agency 6

Oshkosh, WI • On-site

$85K - $100K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Posted 8 days ago

Job description

Job Type
Full-time
Description
CESA 6 is hiring an IT Manager, come join our team!
CESA 6 offers great benefits for full time employees such as: Health, Dental and Vision insurance; Wisconsin Retirement System (WRS); Wellness Program; Accident/Critical Illness/Hospital Indemnity insurance; Pet insurance; paid vacation and holidays.
See CESA 6 Values Here
SUMMARY
The Internal Information Technology Manager leads a small, high-performing team responsible for managing the agency's internal IT infrastructure, systems, and user support operations. This role combines strategic foresight with operational excellence to ensure that CESA 6's technology environment is secure, efficient, and compliant. Operating within a SOC 2 Type 2 compliant control environment and using the Entrepreneurial Operating System (EOS) model, the Manager ensures that technology systems uphold the agency's security, compliance, and service standards. The position balances hands-on technical leadership with strategic management, fostering a proactive service culture and continuous improvement mindset. The Manager oversees one Senior Support Specialist and one Youth Apprenticeship Intern and reports directly to the Chief Financial & Operating Officer (CFOO).
ESSENTIAL FUNCTIONS
Leadership and Management Responsibilities:
  • Lead, manage, and hold accountable (LMA) a small IT team consisting of a Senior Support Specialist and a Youth Apprenticeship Intern.
  • Conduct one-on-one meetings, quarterly conversations, and provide regular feedback and coaching to support performance and development.
  • Establish professional development and skill-building plans that promote professional growth, innovation, and continuous improvement.
  • Foster a collaborative, solution-oriented culture that reflects agency core values and EOS principles.
  • Define clear roles, responsibilities, priorities, and performance expectations, using EOS tools, including scorecards and Rocks, to drive accountability and results.
  • Collaborate with Human Resources in the recruitment, selection, assignment, contracts, and evaluation of department personnel.

Strategic Planning and Implementation:
  • Develop and implement IT strategies, policies, and procedures aligned with agency goals, SOC 2 controls, and EOS processes.
  • Serve as a strategic advisor to the CFOO and Executive Leadership Team on technology planning, risk mitigation, and innovation.
  • Lead IT initiatives from conception to implementation, including budgeting, project management, and communication with internal stakeholders.
  • Evaluate emerging technologies and trends to improve operational efficiency and data security.
  • Align IT initiatives with agency-wide strategic objectives, business continuity planning, and scorecard metrics.

Information Security Officer Responsibilities:
  • Ensure SOC 2 Type 2 controls are implemented, monitored, and evidenced with fidelity, coordinating documentation and requests through the CFOO and external auditors.
  • Oversee IT risk management practices, including cybersecurity, system access and permissions, vendor risk, data privacy and protection, incident response, disaster recovery, cybersecurity recovery, and business continuity.
  • Recommend agency policy revisions and develop administrative rules in alignment with policy related to information security, cybersecurity, data protection, access management, acceptable use, and device management.
  • Lead the annual SOC 2 readiness and evidence collection process, ensuring remediation of any identified findings.
  • Coordinate and document system access and permission reviews, disaster recovery and business continuity testing, penetration testing, vulnerability management, and other cybersecurity testing activities to verify the effectiveness of controls and the agency's ability to recover from operational or cybersecurity disruptions.
  • Ensure IT and security practices comply with agency administrative rules, contractual obligations, and applicable regulatory requirements, including appropriate safeguards to prevent unauthorized access, disclosure, transfer, loss, or removal of CESA 6 data.

IT Infrastructure Management:
  • Oversee the design, configuration, and maintenance of the agency's internal IT environment, including networks, cloud-based platforms, end-user devices, and telecommunication systems.
  • Manage identity and access controls, account provisioning, and integrations across various agency systems, including Google Workspace, Microsoft Azure, NetSuite, and HubSpot.
  • Ensure high system availability, disaster-recovery readiness, and proactive performance monitoring to meet uptime targets.
  • Manage endpoint device lifecycle and inventory in accordance with administrative rules (e.g., PC/Mac distribution, printing, and device security).

User Support and Service Delivery:
  • Promote a culture of exceptional internal customer service, with a focus on responsiveness and effective communication.
  • Lead the internal IT Help Desk operations and ensure timely and effective resolution of user issues and requests.
  • Develop and monitor Service Level Agreements (SLAs) and helpdesk metrics (response times, resolution rates, uptime).
  • Implement and manage self-service solutions, such as an IT Helpdesk Portal and a knowledge base, to increase efficiency.
  • Provide technology training and guidance to staff to promote digital fluency and operational confidence.

Vendor Management and Budget Oversight:
  • Evaluate, select, and manage technology vendors, ensuring alignment with SOC 2 vendor risk management and documentation standards.
  • Negotiate and manage vendor contracts, renewals, and performance reviews.
  • Develop and manage the IT budget, including forecasting, cost optimization, and capital planning.
  • Track and report technology spending to ensure alignment with agency financial policies and operational priorities.
  • Recommend investments that optimize both cost and service delivery efficiency.

OTHER FUNCTIONS
  • Assist with high-severity requests or issue escalations as needed.
  • Perform other duties as assigned by the CFOO.

Requirements
POSITION QUALIFICATIONS
Experience, Education, and Licensure:
  • Associate's or bachelor's degree in Information Technology, Computer Science, Cybersecurity, Information Systems, or a related field, or an equivalent combination of education, industry certifications, and relevant professional experience.
  • Minimum of five years of progressive professional experience in information technology or a related field.
  • Demonstrated experience managing IT infrastructure, cloud and hybrid environments, network administration, identity and access management, cybersecurity, and communications systems, including technologies such as Microsoft Entra ID, Cisco Meraki, Verkada, and 3CX.
  • Demonstrated project management experience, including the ability to lead and execute technology initiatives.
  • Experience with SOC 2 or comparable security and compliance frameworks, including access controls, vendor risk management, and audit evidence documentation, preferred.
  • Demonstrated experience with strategic planning, technology budgeting, and financial management, and aligning technology priorities with organizational goals.
  • Experience with Google Workspace for Education or comparable educational technology environments.
  • Experience working within education, public sector, or nonprofit organizations preferred.
  • Relevant professional certifications, such as ITIL, CompTIA, Microsoft, Cisco, Google, or project management certifications, preferred.

Required Skills and Abilities:
  • Exhibit and model the core values of the agency.
  • Demonstrate strong problem-solving, decision-making, and troubleshooting skills with a focus on timely resolution and results.
  • Maintain strong knowledge of information technology, cybersecurity, and current technologies relevant to educational environments.
  • Communicate and collaborate effectively with executive leadership, staff, clients, and diverse teams.
  • Demonstrate strong organizational, project management, and time-management skills, with the ability to prioritize multiple responsibilities and meet deadlines.
  • Adapt effectively to changing priorities, technologies, and organizational needs while working independently and collaboratively.
  • Maintain confidentiality and handle sensitive information with discretion, integrity, and sound judgment.
  • Demonstrate professionalism and a strong service orientation while consistently applying agency policies, procedures, and service standards.

WORK ENVIRONMENT / PHYSICAL DEMANDS
Work Environment:
  • Ability to work effectively in professional office and other CESA 6 work environments, with or without visual and auditory distractions.
  • Ability to travel between CESA 6 facilities and other off-site locations as required.
  • Valid driver's license and ability to operate a motor vehicle for work-related travel.
  • Position may occasionally require extended hours, including evenings and weekends, and out-of-town travel.

Physical Demands:
  • While performing the duties of this position, the employee is required to stand, walk, sit, use hands to finger, handle, or feel, and reach with hands and arms.
  • Must have the stamina to perform physically demanding tasks for extended periods.
  • Must have adequate vision and hearing to troubleshoot technology issues and identify equipment status lights.
  • The employee must be able to communicate effectively.
  • The employee may occasionally lift or move technology equipment and supplies up to 40 pounds.

Salary Description
$85,000 - $100,000

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