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IT Lead, Systems Administrator

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: ClassDojo
Full Time position
Listed on 2026-10-30
Job specializations:
  • IT/Tech
    Systems Administrator
Salary/Wage Range or Industry Benchmark: 185000 - 220000 USD Yearly USD 185000.00 220000.00 YEAR
Job Description & How to Apply Below

Class Dojo's goal is to give every child on Earth an education they love. We started by building a powerful network for communication. Class Dojo’s flagship app is the #1 communication app connecting K-12 teachers, children, and families globally. Teachers use it to share what’s happening throughout the day through photos, videos, and messages that make parents feel like they’re there.

It’s actively used in over 95% of US schools, reaching over 45 million children in 180 countries, with a team of just around 200 people [1]. We are now beginning to use this network to give kids the best learning experiences in the world, far beyond those a standard school can provide. We hire for talent density. Our team comprises the most talented, entrepreneurial, and innovative teammates from around the world, with experience in education and large scale consumer internet companies, including Instagram, Netflix, Dropbox, Stripe, Uber, Y Combinator, and more.

We’re building a company where the most talented people want to work. We believe you’ll do the best work of your life here—and you’ll pioneer the future of education, too.

As IT Lead you are Class Dojo's IT function; owner & operator, reporting to the CTO, covering identity, devices, SaaS, security operations, vendors, and our AI platforms for roughly 350 people. The function already runs on automation and AI-assisted triage rather than effort. You inherit it with a documented handover, keep it efficient, make it yours, make it better, and make it legible to people who are not you.

What you’ll do:
  • Own identity and the employee lifecycle:
    Okta, Google Workspace, and an HRIS-driven pipeline where access changes fire automatically with an audit trail the systems produce.
  • Own a Mac-first MDM fleet at near-100% coverage, passwordless authentication at 100%, and assist response on security incidents.
  • Run and own IT operations end to end: onboarding, offboarding, support, and the AI triage and self-service that handle most of it, treating repeat request as a defect to remove.
  • Govern a 50+ tool SaaS stack, the IT budget and vendors.
  • Apply governance for Claude and ChatGPT accounts, use AI and automation to take manual work out of IT.
  • Keep IT-owned SOC 2 controls audit-ready with evidence that comes from the systems.
You will be a match if:
  • You have owned and operated IT alone at 200+ staff, including identity in Okta, Google Workspace, and Slack, and a HRIS-driven lifecycle that ran unattended.
  • You have owned a production Mac fleet under MDM, including a migration or baseline rebuild.
  • You have administered ChatGPT and Claude (or comparable) for a company, use them daily, and have built automations that replaced manual IT work with a measurable result.
  • You automate by default: script, API, log, admin console, and you can automate entire request categories.
  • You have practical security judgment and have worked inside a SOC 2 environment.
  • You support people directly and well, and can quote your own support numbers.
  • You write documentation people follow and explain technical decisions to executives in two sentences.
  • You have an ownership mindset and do not wait for perfect requirements or handoffs.
  • You live in the US, East or West Coast, and can travel to San Francisco.
Bonus - You have experience with:
  • AWS IAM Identity Center and Terraform, or other config-as-code you could apply to Okta and Google.
  • Office buildouts, BYOD policy rollouts, international contractors, Windows and ChromeOS [1]

We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. In accordance with the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records. We are happy to accommodate any disabilities or special needs. We are a distributed company, so we hire regardless of location, as long as you are willing to have significant hours overlap with one of the Americas time zones.

Class Dojo takes a number of factors into consideration when determining compensation, including geographic location, experience, and skillset.

Salary ranges (United States): CA, WA, NY, NJ, CT states: $185,000 - $220,000 (USD) All other states in the US: $157,500 - $187,000 (USD)

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