Help Desk Technician

Outcome Insurance Solutions is seeking a reliable, technically skilled, and customer-focused Help Desk Technician to provide first-level technical support to employees and authorized users. The successful candidate will troubleshoot hardware, software, network, account-access, and application-related issues while providing clear and professional assistance.

The Help Desk Technician will serve as an important point of contact for technical support requests and will work closely with internal teams and technology providers to resolve issues efficiently. This position requires strong problem-solving abilities, excellent communication skills, attention to detail, and the ability to prioritize multiple support requests.

Because Outcome Insurance Solutions operates in the insurance industry, the successful candidate should also understand the importance of data security, confidentiality, system availability, and accurate handling of customer and business information.

Key Responsibilities

• Provide first-level technical support through phone, email, chat, ticketing systems, and other approved communication channels.
• Respond to employee technical-support requests promptly and professionally.
• Troubleshoot hardware, software, operating-system, application, printer, peripheral, and connectivity issues.
• Assist users with password resets, account access, multi-factor authentication, and other approved access-management procedures.
• Install, configure, update, and maintain approved software and hardware.
• Assist employees with Microsoft 365, email, web browsers, collaboration platforms, and other business applications.
• Diagnose basic network and connectivity problems and escalate complex issues when necessary.
• Create, update, prioritize, and close help-desk tickets accurately.
• Document troubleshooting steps, resolutions, and relevant technical information.
• Escalate unresolved or complex problems to senior IT personnel, vendors, or appropriate technical teams.
• Follow up with users to confirm that technical issues have been resolved.
• Maintain accurate records of company technology assets when required.
• Assist with employee onboarding and offboarding by preparing equipment, accounts, applications, and access according to established procedures.
• Support remote employees with workstation and connectivity issues.
• Monitor recurring technical issues and communicate trends to IT management.
• Assist with software updates, security patches, and routine technology maintenance.
• Follow company cybersecurity, privacy, access-control, and information-security procedures.
• Protect confidential company, employee, customer, and insurance-related information.
• Participate in IT projects, system upgrades, testing, training, and documentation activities.
• Perform other technical-support and administrative duties as assigned.

Qualifications

• High school diploma or equivalent required; associate or bachelor's degree in Information Technology, Computer Science, or a related field is preferred.
• Previous help-desk, technical-support, IT-support, or customer-service experience preferred.
• Working knowledge of Windows operating systems, Microsoft Office/Microsoft 365, email, web browsers, and common business applications.
• Familiarity with troubleshooting computers, printers, peripherals, software, and basic network connectivity.
• Strong analytical and problem-solving abilities.
• Excellent written and verbal communication skills.
• Ability to explain technical concepts to non-technical users in simple language.
• Strong attention to detail and documentation skills.
• Ability to prioritize multiple support tickets based on urgency and business impact.
• Strong customer-service orientation and professional demeanor.
• Ability to work independently while collaborating effectively with a remote team.
• Ability to learn new technology platforms quickly.

Preferred Qualifications

The following qualifications are helpful but may not be required:

• CompTIA A+, Network+, or similar technical certification.
• Experience with help-desk or ticketing platforms.
• Experience with Microsoft 365 administration.
• Familiarity with Active Directory or cloud-based identity-management systems.
• Experience supporting remote employees.
• Basic understanding of TCP/IP, DNS, VPNs, Wi-Fi, and network troubleshooting.
• Experience in insurance, financial services, healthcare, or another industry where confidential customer information is handled.

Remote Work Requirements

This position is designed for remote work. Candidates must have a reliable computer, stable high-speed internet connection, and a professional workspace suitable for technical support.

The Help Desk Technician must be available during assigned working hours and maintain effective communication with employees, supervisors, and technical vendors through approved communication platforms.

Remote employees must follow all company policies concerning cybersecurity, passwords, authentication, device security, confidential information, and remote access. Company systems and information must only be accessed through authorized equipment, applications, and procedures.

Ideal Candidate

The ideal candidate is patient, technically curious, organized, and service-oriented. You should enjoy solving problems and helping people overcome technical challenges.

A strong Help Desk Technician understands that technical knowledge is only one part of the role. Users may be frustrated when they cannot access a system or complete an important task, so the ability to remain calm, listen carefully, communicate clearly, and provide practical solutions is essential.

You should also be comfortable investigating problems systematically rather than immediately escalating every issue. When escalation is necessary, you should provide clear documentation so that the next level of support can resolve the issue efficiently.

Performance Expectations

Success in this position may be evaluated based on:

• First-response and resolution times.
• Number and quality of successfully resolved tickets.
• User satisfaction.
• Accuracy of troubleshooting documentation.
• Compliance with security and IT procedures.
• Ability to meet service-level expectations.
• Effective communication with users and technical teams.
• Accuracy of equipment and system records.
• Reliability and schedule adherence.
• Ability to identify recurring issues and recommend improvements.

Compensation

Salary Range: $25–$35 per hour, depending on experience, technical qualifications, certifications, location, and responsibilities.

At 40 hours per week, this represents an approximate annualized range of $52,000–$72,800 before taxes, assuming 52 paid weeks.

This salary range is presented as a proposed job-posting range, not a verified current Outcome Insurance Solutions compensation figure. Applicants should confirm the actual compensation, benefits, employment classification, and remote-work eligibility directly with the company before accepting an offer.

What We Offer

Outcome Insurance Solutions provides an opportunity to work in a professional environment while developing valuable experience in technical support, cybersecurity awareness, business applications, remote IT operations, and customer service.

The selected candidate will receive appropriate training regarding company systems, security procedures, support processes, and technical standards.

Equal Opportunity Statement

Outcome Insurance Solutions is committed to maintaining a professional, respectful, and inclusive workplace. Qualified candidates from diverse backgrounds are encouraged to apply. Employment decisions are based on qualifications, experience, skills, business requirements, and applicable laws.

How to Apply

Interested candidates should submit an updated resume highlighting relevant IT support, help-desk, troubleshooting, technical-service, customer-service, software, networking, or systems experience. Candidates may be asked to participate in a technical assessment or interview as part of the hiring process.

If you are a technically capable, customer-focused professional who enjoys troubleshooting problems and helping users work more effectively, we encourage you to apply for the Help Desk Technician position with Outcome Insurance Solutions.