Technical Operations Specialist, 2 Hour Learning (Remote) - $100,000/year USD

Crossover•Chicago, IL

fulltime

Engineering, Information Technology, and Purchasing

3+ years

About the role

You are not here to process tickets. You are here to run the operational systems that keep an organization moving. If you have managed endpoint fleets, controlled SaaS access, and handled procurement under real deadlines, this role represents a meaningful next step. If you prefer a slower IT environment where change is rare and launch timelines belong to others, this is not the right match.

2 Hour Learning is expanding a new K-12 model driven by AI-powered personalized learning. As campuses open on a consistent schedule, the line between "prepared" and "unprepared" often comes down to operational fundamentals: devices that are ordered, provisioned, and enrolled; SaaS licenses that are active and correctly assigned; communication tools that are configured and verified.

This role places you in charge of device procurement spanning Dell, HP, Apple, and Lenovo; MDM (mobile device management) administration and provisioning processes; SaaS account and renewal management across 14+ platforms; and campus technology onboarding execution (covering Google Voice, Zoom Phone, and Zoom Rooms). You will capture what succeeds, refine the standard operating procedures, and apply AI tools to automate recurring tasks.

If you seek direct ownership, trackable results, and the momentum of an expanding school network, we want to speak with you.

What You Will Be Doing

Manage complete device procurement workflows across Dell, HP, Apple, and Lenovo, monitoring lead times and shipment schedules to ensure campuses receive equipment ahead of launch dates
Handle provisioning, imaging, enrollment, and lifecycle management of student and staff devices via an MDM platform, maintaining precise asset documentation across all campuses
Oversee SaaS account administration, user permissions, and license allocation across 14+ platforms, anticipating utilization thresholds and renewal cycles to avoid service interruptions
Deploy the new-campus technology onboarding playbook, preparing devices, provisioning systems, and setting up Google Voice, Zoom Phone, and Zoom Rooms in advance of opening day
Create and update SOPs, runbooks, and launch checklists, refining processes with each campus onboarding cycle and leveraging AI tools to automate routine activities

What You Won’t Be Doing

Functioning primarily as a ticket-driven helpdesk technician whose performance is judged by volume metrics
Architecting long-term IT strategy or participating in strategic discussions while launch deadlines are missed
Managing unplanned purchases without inventory tracking, vendor management, or documented specifications
Relying on others to create process documentation (you will ensure launches are repeatable and not reliant on institutional knowledge)

Technical Operations Specialist Key Responsibilities This position ensures that each campus opens and runs according to plan because devices, SaaS access, and launch-critical technology systems are completely provisioned and operational before the first day.

Basic Requirements

Currently based in the United States with authorization to work in the US without requiring visa sponsorship
Available and willing to travel periodically to US campuses
Proven experience managing an MDM (mobile device management) platform such as ManageEngine, Jamf, Intune, Mosyle, or similar
Direct experience deploying and supporting end-user devices (laptops or tablets), including provisioning/imaging and troubleshooting tasks
Background in administering SaaS platforms, covering account provisioning, permissions control, and license oversight
Track record coordinating hardware procurement and delivery operations and/or managing asset tracking processes
Demonstrated ability to create or maintain operational documentation including SOPs, runbooks, or playbooks
Confirmed experience using AI tools to diagnose technical issues or automate repetitive operational tasks

Nice-to-have Requirements

Background supporting a multi-site, distributed environment requiring inventory, spare parts, and repair coordination across locations
Proven ability to develop straightforward automations that minimize manual provisioning and reporting effort
Hands-on experience setting up or managing communication platforms such as Google Voice, Zoom Phone, or Zoom Rooms

About 2 Hour Learning Education is broken, but 2 Hour Learning is proving it doesn’t have to be. They’re tearing down the outdated one-size-fits-all model and replacing it with AI-driven personalized learning that helps kids master academics in just two hours a day.

With students consistently ranking in the top 1-2% nationally and the top 20% achieving an astonishing 6.5x growth, they’re proving that smarter learning is possible. At 2 Hour Learning, it’s talent and performance that matter. They offer a dynamic, on-campus and remote-friendly environment where innovators, educators, and AI specialists can be a part of fixing a broken school system.

2 Hour Learning is reprogramming learning for the AI era. Here’s How They’re Fixing It. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $50 USD/hour, which equates to $100,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help\-and\-faqs for more details on this topic.

Crossover Job Code: LJ-5755-US-Chicago-TechnicalOpera

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