Description
Educational support organizations face mounting complexity as schools, students, and families demand higher levels of service. Today's institutions require immediate, AI-driven responses spanning learning platforms, student information systems, devices, and operational processes. Yet many teams remain trapped in disconnected tools, manual handoffs, and fragile systems that buckle when tested in live environments.
We address this challenge through a distinct approach: AI-enhanced "cyborg" agents functioning at the core of an active educational environment. In this position, you will influence how the system evolves. Each resolution refines future automation, each root cause investigation shapes process and policy, and each complex scenario you decode strengthens outcomes for thousands of students and educators.
This is direct, production-level problem solving within a service context. You will diagnose unclear, multi-party failures across learning applications, SIS platforms, identity systems, networks, and operational processes; use AI to generate hypotheses, test assumptions, and expedite resolution strategies; capture the human logic that educates both systems and colleagues; and proactively surface patterns that convert isolated fixes into lasting, organization-wide improvements.
This is not ticket sorting, checklist execution, or "escalate and wait." If you excel when documentation is sparse, when problems cross engineering, operations, and academic domains, and when you can shift from technical diagnosis to stakeholder coordination without sacrificing precision, this role will suit you well.
What you will be doing
- AI-Augmented Customer Resolutions: Examine complex tickets escalated by AI systems, apply human judgment to domains where AI underperforms, and then bridge the gap by refining the AI system
What you will NOT be doing
- Taking two whole months to get up to speed; you will be expected to ramp up on several products within the first month (we are aware this is aggressive)
- Relying on your managers for help; if you are not adept at unblocking yourself, you will likely struggle in this role
Key responsibilities
- Combine technical human expertise and AI capabilities to provide exceptional customer support, concentrating on complex issues that AI cannot yet fully address
Candidate requirements
- Must be based in North or South America
- At least 3 total years of experience in a technical customer support role
- Basic coding skills for the purpose of troubleshooting/bug fixes
- Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you've only used LLMs for research, learning, brainstorming, or content generation, that will be deemed insufficient
- Troubleshooting Skills: Explaining complex issues in simple terms, demonstrating strong problem understanding, recommending relevant troubleshooting strategies, proposing multiple solution paths, and showing attention to detail
You will be working for
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Accept job offer.
Pass
proctored test.
Frequently asked questions
Reviews
Meet some people who've landed similar jobs
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.