IT Support Specialist
Toronto, ON
Job Description

Help Square revolutionize the way people make and accept payments. We’re looking for an IT Support Specialist to join our IT team. This is a great opportunity to work and grow with a fantastic company, learning more and more every day. We are predominantly OS X, with a growing Windows and Chrome OS environment, requiring a motivated self-starter who is eager to learn more.

You will:
Provide front-line support for Square workers

Image computers

Field questions

Migrate Squares to new machines

Deploy software and provide access to Squares

Help with A/V setup for internal events

Assist with desktop automation


You have:
OS X + Windows + ChromeOS end-user support experience

Fantastic deskside manner

Good problem solving and pattern recognition

Have a basic understanding of connecting computers to networks

Ability to quickly assess root cause, and implement and share corrections

Willingness to collaborate on development and upkeep of knowledge base articles

Ability to lift 50+ lbs computer equipment and hardware, climb ladders and use hand tools where necessary

Even Better:
Powershell and Active Directory administration understanding

VOIP administration experience

Experience building Windows images

Previous work experience in a startup environment

Command-line Unix experience

Other Unix/Linux experience (Shell scripting)

Experience with Munki

Being a serious A/V person will help in many ways

A college degree is helpful, but actual industry experience and knowledge is key

Additional Information

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at) We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible.