Technical Support Specialist

Flywire; Woburn (MA); On-site; USD 52,000 - 66,000; Full time

Benefits offered by this job

Health benefits

401(k) plan with match

Wellness reimbursement

Employee assistance program

Job summary

Flywire is seeking a Technical Support Specialist to deliver front-line technical help for Apple devices to in-office and remote staff. You will troubleshoot issues, set up equipment, and help with accounts while maintaining clear customer communication.

You will join a team that values problem-solving and rapid learning, with opportunities to grow into higher-level technical roles.

Qualifications

• High School Diploma or equivalent required.
• Basic knowledge of Apple macOS and iOS devices.
• Familiarity with Wi-Fi and basic networking concepts.
• Experience with Microsoft Office applications.
• Customer service mindset with strong communication skills.

Responsibilities

• Provide first-level technical support for Apple devices to on-site and remote users.
• Troubleshoot hardware and software issues and document resolutions.
• Set up and maintain end-user equipment and accessories.
• Assist with user account setup and password resets.
• Escalate complex issues to senior staff when needed.
• Track requests via ticketing system and maintain knowledge base entries.

Skills

Apple/macOS

Apple iOS devices

Networking basics

Microsoft Office

Problem solving

Customer service

Communication

Ticketing systems

Education

High School Diploma or equivalent

CompTIA ITF+ or A+ certification

Job description

Job Description

Position Overview

Reporting to the Technical Services Supervisor, the Technical Support Specialist provides front-line technical support to both in-office and remote employees. This role is ideal for someone early in their IT career who enjoys problem-solving, learning new technologies, and delivering excellent customer service.

Key Responsibilities

• Provide first-level technical support for Apple devices, including MacBooks, iPhones, and iPads.
• Troubleshoot and resolve basic hardware and software issues for employees working in-office and remotely.
• Set up, configure, and maintain end-user equipment and accessories (keyboards, mice, monitors, printers, etc.).
• Assist with user account setup, password resets, and basic application support.
• Document common issues, resolutions, and procedures for inclusion in the company knowledge base.
• Escalate complex or unresolved issues to senior technical staff as appropriate.
• Track and manage support requests through a ticketing system to ensure timely resolution.
• Maintain a high standard of customer service and clear communication with all users.

Qualifications

Required Technical Skills

• Basic working knowledge of Apple macOS and iOS devices.
• Fundamental understanding of Wi-Fi and basic networking concepts.
• Basic proficiency with Microsoft Office (Outlook, Word, Excel, Teams).
• Ability to follow technical instructions and learn new systems quickly.

Core Competencies

• Strong verbal and written communication skills.
• Customer-focused mindset with a helpful, patient approach.
• Strong organizational skills and ability to prioritize multiple tasks.
• Attention to detail and commitment to accurate documentation.
• Dependable, punctual, and able to work independently with minimal supervision.

Education & Experience

• High School Diploma or equivalent required.
• Prior experience in a technical support, IT help desk, or customer service role is a plus but not required.
• Relevant coursework, certifications (e.g., CompTIA ITF+, A+), or hands‑on technical projects are a plus.

Work Schedule & Location

• On-site position, Monday through Friday, 8:30 a.m. – 5:00 p.m.
• Occasional flexibility may be required based on business needs.

Pre-Employment Requirements

• Ability to pass a 10-panel drug screening.
• Ability to pass a criminal background check.

Additional Information

Our Benefits – Supporting You Inside and Out

medical, dental, and vision coverage through UnitedHealthcare and Guardian , employer-paid life and disability insurance , and a 401(k) plan with company match. We also invest in your wellness — with up to $100 annual reimbursement for fitness, mindfulness, and wellness activities, plus access to mental health tools like the Calm Health app and a 24/7 Employee Assistance Program. From flexible spending accounts to nationwide fitness programs and virtual care, PFA is committed to helping you stay healthy, balanced, and thriving — at work and beyond.

• medical, dental, and vision coverage through UnitedHealthcare and Guardian
• employer-paid life and disability insurance
• 401(k) plan with company match
• $100 annual reimbursement for fitness, mindfulness, and wellness activities
• access to mental health tools like Calm Health app
• a 24/7 Employee Assistance Program
• flexible spending accounts
• nationwide fitness programs
• virtual care