Escalation Engineer, Alpha

Role overview

In this role, you become the person who takes over when standard support and AI-based troubleshooting have already been exhausted. You will handle difficult issues affecting Alpha’s learning platform, reproduce them in environments that match the user’s device and setup, and determine the true source of the problem. Because these tools are used in classrooms, accuracy matters: the expectation is to fix issues with as few back-and-forth interactions as possible and to validate every result before anything is considered resolved.

The work is varied and fast-moving. You may spend one day investigating a lesson that will not open for a student and the next correcting inaccurate mastery data in a guide-facing interface. New product surfaces and workflows are introduced regularly, so learning new systems quickly is part of the job rather than an occasional requirement.

What you will do

• Take ownership of complex support cases that neither AI nor first-line support could close successfully.
• Recreate problems in an environment that mirrors the user’s device, app version, and configuration, using real artifacts, logs, and other evidence.
• Investigate issues across Alpha’s learning ecosystem, including ticketing tools, Slack conversations, knowledge resources, and log files, before deciding whether escalation is needed.
• Use AI tools such as ChatGPT or Claude to speed up analysis, while grounding every conclusion in verified documentation and checking all AI-generated outputs yourself.
• Ask non-technical users clear, targeted questions so you can gather the right details and solve the issue efficiently.
• Escalate genuine product defects to engineering with complete diagnostic context.
• Record your troubleshooting steps and findings so future support agents and AI workflows can reuse the knowledge.

What you will not be doing

• You will not follow rigid scripts or fixed decision trees for one narrow product.
• You will not handle only easy tickets that can be solved by simple knowledge-base searches.
• You will not send issues to engineering before first reproducing and narrowing down the cause.
• You will not rely on AI output without checking it carefully yourself.
• You will not wait for others to unblock you or provide direction before moving forward.

About the company

Alpha School aims to change the way education works by using AI to help students learn core academics faster and free up time for hands-on, interest-based learning. The broader mission is to challenge traditional classroom models and build a new approach to education.

Employment terms

This is a full-time, long-term contractor role, delivered through an independent contractor agreement with Crossover as Contractor of Record. The position is available immediately. The work schedule is 40 hours per week on a US daytime schedule, specifically during Eastern Time business hours. Payment is made weekly.

The compensation is $30 USD per hour, which equals $60,000 USD per year based on 40 hours per week and 50 weeks per year.

Additional information

Applicants should be comfortable with frequent ramp-up on new products and should be motivated by challenging, ambiguous problems that directly affect children’s learning experiences.

Crossover Job Code: LJ-5729-IE-Dublin-EscalationEngi

Location

The role is open to candidates located in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines.

Working style

Success in this role depends on strong independent problem-solving, careful validation, and the ability to communicate clearly with both technical and non-technical stakeholders.