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We’re looking for a

Systems Administrator

About Prodigy

In the last nine years, Prodigy Education has grown from 3,000 local users to more than 100 million registered users worldwide. As one of the fastest-growing ed-tech startups in North America with global impact, Prodigy connects students, parents, teachers, and school districts with resources that promote a lifelong love of learning. Anyone with an internet connection is welcome to create a free account for its renowned Math Game and try an effective and engaging math platform for grades 1 to 8. For more information visit, or @ProdigyGame on Twitter.

At Prodigy Education, we have an incredible team that works tirelessly to turn our goal of making education a human right into a reality. We are immensely grateful for our amazing team and all they do every day. We welcome people who share our passion to join our team, where you will have the opportunity to help an entire generation of students to LOVE learning.

Our passion is our mission - to help every student in the world love learning!

Please note: During the Covid-19 pandemic, in order to keep all our candidates safe, Prodigy is hiring and on-boarding 100% remotely for the time being.


  • Here at Prodigy, we are working hard to achieve our mission of helping every child in the world to LOVE learning. Our Engineering teams are scaling rapidly as we continue to hit our product and growth milestones, and it’s an exciting time for the company! To continue our exponential growth, we are adding some more management power to our IT team. As a Systems Administrator at Prodigy, we would be looking to you to both maintain, manage and implement new IT systems and services while bridging important communication gaps to enable us to streamline security and better support our incredible team!

Your Impact:

  • You will administrate Prodigy's Okta and third party SaaS environment consisting of roughly 200 SaaS tools
  • You will assist with the planning and implementation of third party applications and Okta integrations
  • Design and upkeep interconnected employee directories through automated on-boarding/off-boarding workflows
  • You will assist with maintaining relationships for IT systems and third party application vendors
  • Manage and maintain mobile device management and anti-virus systems
  • You will assist other business units identify key areas where IT management systems may improve workflows/processes, and consolidate tools across the organization
  • Research and develop new strategies to improve IT system performance, automation and security
  • Provide mentorship and guidance to co-workers in the area of System Administration.
  • Install and provide regular maintenance for internal IT systems such as video conferencing, RADIUS servers, etc
  • Develop automated scripts/builds for on-boarding new employee hardware
  • Work with IT Support and Network Administration personnel to troubleshoot issues
  • Maintain a secure a stable environment through secure administration processes
  • Create and maintain in-depth documentation of company’s existing infrastructure, asset tracking systems, and directories
  • Act as the IDP and internal system subject matter expert (SME) for technical initiatives, innovation and ongoing support

Who You Are:

  • You have a minimum of 5 years experience working in IT, with 2 years working in a Systems related role
  • You are a diligent problem solver and communicator, passionate about collaborating, streamlining and improving upon internal IT processes and systems
  • You are experienced with working in a primarily cloud based IT environment controlled by a centralized IDP
  • You have experience working with Okta or an equivalent IDP, and are experienced in setting up SAML based integrations
  • You are comfortable working in a primarily Mac based environment and have experience using JAMF or an equivalent MDM solution
  • You are excited by the challenges that come with a rapidly growing and scaling company, and have thrived in this kind of environment
  • You have experience designing and working with multiple interconnected directory structures and have workflows
  • Coaching and mentorship is your passion - you thrive on seeing your team members grow and develop personally and professionally
  • You're not afraid to stretch yourself outside of your comfort zone to take on new challenges, and have a love for continuous learning
  • You are comfortable with occasional after hours work on IT systems and supporting remote users
  • You have a good understanding of proper user access flows and security
  • You are comfortable with commuting between our Oakville and Toronto offices
  • You are well organized and strategic in your day to day tasks
  • You have a strong triage mindset when multiple issues and situations arise

Our Core Technologies:

  • Operating Systems: MacOS, Windows, Windows Server
  • Admin: Okta, AzureAD, GSuite, Atlassian/Confluence/Jira
  • Antivirus: TrendMicro Apex One
  • Collaboration: Slack, Zoom

Bonus Point For:

  • Certification with JAMF or a related MDM solution
  • Networking knowledge
  • A strong passion for education
  • Previous experience scaling in a startup environment

What We Offer:

  • The opportunity to build a career of value and witness first hand the impact Prodigy has as the most engaging math platform in the world!
  • A culture of transparency, where team members are involved in important conversations
  • No micromanaging here! We believe in our employees skills and abilities, we encourage you to bring new innovative ideas to your team
  • Full health benefits from day one (1)  for you and your family, fully covered! Nothing is ever taken off your pay cheque 
  • We are a profitable company, with eligibility to participate in stock options for all employees
  • Late or early riser? We understand! We offer flexible working hours that allow you to schedule your 8 hour day with a bit more flexibility. We do have core office hours, to ensure team members can be present for important meetings and department needs. Our core office hours are 10:30am - 3:00pm

  • While we operate 100% remotely for the time being, our company culture and values remain at the core of everything we do. We are offering a number of remote-friendly activities such as:
  • Virtual trivia 
  • Zoom meditation, stretching, and fitness sessions
  • Daily remote challenges via Slack 
  • Virtual “Prodigy Prepares” cooking series featuring our very own employees!
  • Remote work employee budget for things like home office equipment etc. 

  • When this pandemic comes to an end and it is safe to be back in the office. Here's a glimpse into what you can expect: 
  • Feel like working from home ? Prodigy is office optional!
  • Team building events that not only include you as a Prodigy employee, but your significant other and children as well
  • Company pizza lunch every second week for ‘All Hands’, where we discuss important Prodigy milestones
  • Do you need some fun to help break up your day? We have that covered! Join in some Ping Pong games, Smash Bros competitions or board games!
Apply for this position

Department: Operations

Location: Oakville, Ontario

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Come as you are. We believe the power of our collective potential will transform education. We are building towards a diverse, inclusive, and equitable workplace to empower and create access and opportunity for all. We welcome applications from people from all underrepresented groups, including (but not limited to) people of any gender, age, or religion, members of the LGBTQIA2+ community, BIPOC and other underrepresented races and nationalities, people with disabilities, veterans, and anyone who may contribute to the further diversification of Prodigy Education. If you feel like you don’t have all the qualifications for this position, and are willing to use your initiative to learn the rest, we’d still love for you to apply! We are an equal opportunity employer and are committed to providing employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act, 2005 (AODA). Prodigy Game will provide accommodations to job applicants with disabilities throughout the recruitment process. If you require an accommodation, please notify us and we will work with you to meet your needs.