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Remote It Helpdesk Trainee Jobs (NOW HIRING)

On Board Experiential

IT Director

New York, NY · On-site

Oversee IT service delivery and support operations for all employees across offices and remote environments. * Manage the IT help desk ticketing system (ServiceNow) and ensure timely resolution of ...

On Board Experiential

IT Director

New York, NY · On-site +1

Oversee IT service delivery and support operations for all employees across offices and remote environments. * Manage the IT help desk ticketing system (ServiceNow) and ensure timely resolution of ...

On Board Experiential

IT Director

New York, NY · On-site +1

Oversee IT service delivery and support operations for all employees across offices and remote environments. * Manage the IT help desk ticketing system (ServiceNow) and ensure timely resolution of ...

ProTek IT Solutions

IT Support Specialist

Clearwater, FL · Remote

$60K - $100K/yr

... remote support services. We have steadily grown every year since the company's inception, and we are looking to bring on several skilled IT Support Specialists to help with our ever-expanding client ...

Darkhorse Tech, Inc.

IT Help Desk Technician

$40K - $45K/yr

With technicians on the ground throughout the country we offer in-person as well as remote support ... Bachelor's degree in Information Technology or Computer Science is preferred Hours - Monday through ...

CyberSheath

Helpdesk Technician II

Reston, VA · Remote

$83/hr

Minimum of 5+ years' experience working on an Information Technology Helpdesk using remote support tools * Experience using a helpdesk ticketing system for incident tracking and time entry ...

CyberSheath

Helpdesk Technician II

Minimum of 5+ years' experience working on an Information Technology Helpdesk using remote support tools * Experience using a helpdesk ticketing system for incident tracking and time entry ...

CyberSheath

Helpdesk Technician I

$20.50 - $27.75/hr

Minimum of 3+ years' experience working on an Information Technology Helpdesk using remote support tools * Experience using a helpdesk ticketing system for incident tracking and time entry ...

CyberSheath

Helpdesk Technician I

Reston, VA · Remote

$20.75 - $28/hr

Minimum of 3+ years' experience working on an Information Technology Helpdesk using remote support tools  * Experience using a helpdesk ticketing system for incident tracking and time entry ...

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Remote It Helpdesk Trainee information

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How much do remote it helpdesk trainee jobs pay per hour?

As of Jun 25, 2026, the average hourly pay for remote it helpdesk trainee in the United States is $23.15, according to ZipRecruiter salary data. Most workers in this role earn between $19.23 and $25.96 per hour, depending on experience, location, and employer.

What is the difference between Remote It Helpdesk Trainee vs Remote IT Support Specialist?

AspectRemote It Helpdesk TraineeRemote IT Support Specialist
CertificationsEntry-level, often no certifications required or basic certificationsRelevant certifications like CompTIA A+, Network+ preferred
Work EnvironmentTraining environment, supervised, learning-focusedOperational environment, providing ongoing support to users
Job ResponsibilitiesAssisting with basic troubleshooting, learning IT support processesResolving technical issues, maintaining systems, supporting users

The Remote It Helpdesk Trainee is an entry-level role focused on learning and assisting with basic IT support tasks under supervision. In contrast, the Remote IT Support Specialist is a more experienced position responsible for resolving complex technical issues independently. While both roles involve remote support and require foundational IT knowledge, the trainee role emphasizes training and skill development, whereas the specialist role involves active problem-solving and system management.

More about Remote It Helpdesk Trainee jobs
What cities are hiring for Remote It Helpdesk Trainee jobs? Cities with the most Remote It Helpdesk Trainee job openings:
What are the most commonly searched types of It Helpdesk Trainee jobs? The most popular types of It Helpdesk Trainee jobs are:
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Remote It Helpdesk Trainee jobs near you
Infographic showing various Remote It Helpdesk Trainee job openings in the United States as of June 2026, with employment types broken down into 56% Full Time, 42% Part Time, and 2% Contract. Highlights an 37% Physical, 3% Hybrid, and 60% Remote job distribution, with an average salary of $48,154 per year, or $23.2 per hour.

IT Director

On Board Experiential

New York, NY • On-site

Full-time

Medical, Dental, Vision, Life, Retirement, PTO

Posted 13 days ago

Job description

About On Board Experiential (OBE)
OBE is a global marketing agency that brings brands to life through culture-shaping experiences. For more than 30 years, we've partnered with iconic brands - including Nike, the NFL, JPMorganChase, Meta, Sephora, Starbucks, and Converse - to build community, create cultural relevance, and drive measurable business impact. With offices in Los Angeles, New York, San Francisco, and London, we activate globally. OBE is also a founding member of The ADD Collective, extending our reach and resources while staying true to our core capabilities.
We've been recognized by Event Marketer as one of the best places to work in events - and we couldn't agree more.
The most important part of our business is our people. They are hardworking, imaginative, and make genuinely remarkable things happen. But behind every great activation is a human who deserves rest, connection, and a life outside of work. That's why we invest in recovery days, company offsites, happy hours, and the kind of friendly-but-competitive fitness challenges that bond teams for life.
We show up for each other - in open conversations that heal, inspire, and bring us closer. We want to hear about your lived experiences, your unconventional ideas, and the perspectives only you can bring. Being unapologetically yourself isn't just welcome here. It's part of the job.
Summary of Position
The IT Director is a senior leader responsible for the strategic direction, management, and security of the organization's technology ecosystem, including emerging AI capabilities. This role ensures that all OBE offices and personnel have secure, reliable, and scalable systems that support efficient data processing, collaboration, and communication across locations and remote environments.
The IT Director oversees the organization's IT infrastructure, cybersecurity posture, and enterprise technology strategy while identifying opportunities to leverage artificial intelligence, automation, and advanced analytics to improve operational efficiency and business outcomes. This position leads IT operations, vendor partnerships, and technology initiatives across multiple office locations and remote employees while ensuring the protection, integrity, and availability of company information assets.
Essential Job Functions
IT Strategy, Operations & AI Enablement: (30%)
  • Develop and implement IT policies, standards, and best practice frameworks across the organization.
  • Establish and execute the organization's IT and AI strategy aligned with business objectives.
  • Identify and implement opportunities for AI, automation, and data-driven solutions to improve operational efficiency and decision-making.
  • Oversee daily IT operations including infrastructure, systems, cloud services, and enterprise applications.
  • Plan and manage technology upgrades, migrations, and system implementations.
  • Maintain department operational documentation and ensure compliance with applicable laws, codes, and regulations.
  • Develop and manage the IT department budget and ensure cost-effective technology investments.
  • Evaluate, select, and implement technology solutions and enterprise systems that support business growth.
  • Establish timelines and governance for major IT initiatives including infrastructure updates, platform migrations, and system integrations.
  • Stay informed of emerging technologies, cybersecurity trends, and AI advancements relevant to the organization.

Cybersecurity, Risk & Compliance: (20%)
  • Lead the organization's information security management program to safeguard data, systems, and networks.
  • Conduct technical risk assessments across information security, privacy, disaster recovery, infrastructure, emerging technologies, and vendor environments.
  • Identify security gaps and lead remediation initiatives to strengthen the organization's security posture.
  • Maintain incident response, disaster recovery, and business continuity plans.
  • Establish and maintain security policies, training programs, and awareness initiatives for employees.
  • Perform regular system audits and vulnerability assessments across all office locations.
  • Ensure compliance with relevant regulatory and security frameworks, including PCI and vendor security requirements.

Help Desk/In House Technical Support: (20%)
  • Oversee the design, implementation, and maintenance of network, server, cloud, and endpoint infrastructure.
  • Evaluate organizational technology needs and recommend scalable solutions aligned with future growth.
  • Manage hardware lifecycle planning, procurement, and deployment.
  • Oversee email systems, identity management, and access control processes.
  • Maintain accurate technology asset inventories and system documentation.

Service Delivery & Internal Support: (15%)
  • Oversee IT service delivery and support operations for all employees across offices and remote environments.
  • Manage the IT help desk ticketing system (ServiceNow) and ensure timely resolution of technical issues.
  • Oversee employee technology onboarding, provisioning, and support processes.
  • Provide escalation support for complex technical issues when necessary.

Vendor & Technology Partner Management: (10%)
  • Manage relationships with IT vendors, service providers, and technology partners.
  • Negotiate contracts, review Master Service Agreements, and ensure vendor performance aligns with business needs.
  • Evaluate and select external partners for infrastructure, security, and enterprise technology services.

Client & Project Technology Support: (5%)
  • Provide technical oversight and consultation on project-specific technology requirements.
  • Manage hardware and software deployment for client or project initiatives.
  • Support project teams in configuring devices, systems, and profiles as needed.

Desired Skills and Experience
Education
Bachelor's degree in computer science, management information systems, business administration or related field.
Advanced technical certifications or graduate-level education in technology, cybersecurity, or artificial intelligence preferred.
Experience
  • Eight to ten (8-10) years of progressive experience in information technology leadership roles.
  • Experience developing and implementing IT strategy and managing enterprise infrastructure environments.
  • Experience with cybersecurity risk management, regulatory compliance, and disaster recovery planning.
  • Experience implementing AI, automation, or advanced data solutions within business operations preferred.
  • Proven experience evaluating, selecting, and implementing enterprise technology platforms.
  • Experience managing vendor partnerships and negotiating service agreements.
  • Experience working in collaborative, cross-functional environments.

Essential Knowledge, Skills, and Abilities
  • Strong understanding of cybersecurity principles, risk management, and enterprise IT governance.
  • Knowledge of AI technologies, automation tools, and data-driven systems applicable to business operations.
  • Strong communication and presentation skills with the ability to engage technical and non-technical stakeholders.
  • Ability to prioritize initiatives and manage multiple technology projects simultaneously.
  • Strong analytical and problem-solving capabilities.
  • High attention to detail and strong documentation practices.
  • Self-motivated with the ability to lead initiatives in a fast-paced environment.

Software
  • Experience using an IT Support Helpdesk ticket system, such as Service Now
  • Strong knowledge of office system and software configurations, best practices, specifically Microsoft Office Products, including Microsoft 365, Adobe Creative Suite, and Quickbooks
  • Knowledge of encryption both at the file and machine level
  • Ability to maintain general software inventory ensuring legality and tracking
  • Knowledge of Active Directory configuration and replication
  • Strong documentation skills, including Visio/diagramming software

Networking
  • Network architecture including VLANs and secure wireless infrastructure
  • Firewall configuration, policies, and network monitoring
  • Intrusion detection and prevention systems
  • Cloud-based infrastructure and hybrid environments
  • Backup, recovery, and data protection systems

Other Qualities and Skills
  • Strong intellectual curiosity and commitment to continuous learning, especially in emerging technologies and AI.
  • Ability to support and communicate effectively with non-technical stakeholders.
  • High adaptability and flexibility, including occasional evening or weekend work when required.
  • Willingness to work a hybrid schedule (minimum two in-office days weekly) and travel periodically to company offices.
  • Ability to thrive in a fast-paced, creative, and collaborative environment.
  • Strong customer service orientation and leadership mindset.

Compensation Range: $150,000 - $185,000 annually. This is the pay range OBE believes it will pay for this position at the time of this posting. Consistent with applicable law, compensation will be determined based on level of experience, relevant skills, professional certifications, market pay, and demand for the role. OBE reserves the right to modify this pay range at any time. For this role, Benefits include: medical/dental/vision insurance, employer paid basic life and personal accident insurance. Also included: Annual Profit Sharing/Bonus Plan based on the company's performance and your individual performance, 401(k), Healthcare Flexible Spending Account, Dependent Care Flexible Spending Account, PTO, STD/LTD insurance benefits.

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