Technical Support Specialist, Alpha (Remote) - $60,000/year USD
About the role
A student is ready to learn, but the app refuses to load. A guide's dashboard displays incorrect mastery scores. L1 support and the AI have already attempted resolution without success. The issue is now yours — and a child's learning day depends on you identifying what has actually gone wrong.
The majority of your workday will involve tickets that no one else managed to resolve, spanning the diverse applications that comprise Alpha's learning platform. You will replicate the issue in a setup that matches the student's or guide's environment, examine logs and documentation, leverage AI to accelerate your work, and then validate everything it produces, because an incorrect answer delivered to a classroom scales its impact rapidly. Ramping up on a new product nearly every week is expected. This is the nature of the role, not a caution.
Each problem is yours from start to finish: replicate it, identify the underlying cause, and resolve it with the fewest interactions necessary to restore the student or guide's workflow. The documentation you create strengthens the next agent and the next AI system, ensuring your solution continues to add value well beyond your current ticket. In time, you will become the go-to resource the team relies on for its most challenging education-product issues.
If you seek the difficult, unclear problem, and you genuinely care that the product ultimately helps a child learn, submit your application.
What You Will Be Doing
Address unclear, escalated support requests from students, parents, and guides that AI and L1 could not resolve. Replicate issues in environments mirroring the user's device, application, and setup, using logs and actual data. Conduct thorough investigations across Alpha's learning applications (tickets, Slack, knowledge repositories, logs) prior to escalating. Use AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in authentic documentation, and validate all outputs. Engage clearly and professionally with non-technical users, collecting sufficient information upfront to enable single-pass resolution. Escalate issues to engineering with comprehensive diagnostic context when a genuine product defect is confirmed. Record your diagnostic reasoning so future team members and AI workflows can leverage it.
What You Won’t Be Doing
Working from scripts or decision trees for a single product. Managing the simple queue. AI already handles tickets solvable through knowledge-base searches. Escalating difficult problems to engineering without first replicating and isolating them. Allowing AI to do your thinking, or delivering its responses without verification. Waiting for direction, or relying on others to remove blockers.
Technical Support Specialist Key Responsibilities
Diagnose and resolve complex, ambiguous customer issues to their root cause across Alpha's education products.
Basic Requirements
2+ years in a hands-on technical role such as technical support, software engineering, QA, sysadmin, or DevOps. Your job title does not have to be "support." Comfortable constructing and reading REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating in command line and log environments. Practical experience using AI tools (such as ChatGPT or Claude) in daily technical work. Professional fluency in written and spoken English. Available to work full-time (40 hours/week), with all working hours between 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern).
Nice-to-have Requirements
Experience supporting non-technical end users (in education, edtech, or consumer applications), not only IT professionals. Practical experience guiding AI tools and identifying their errors. A proven history of troubleshooting across multiple unrelated products, not a single one. Developer-level proficiency: capable of reading code or tracing an API call when necessary.
About Alpha
Join the team building school around student growth
Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.
Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.
Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience.
A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.
Alpha is where you can do the most meaningful work of your career.
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 $30 USD/hour, which equates to $60,000 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-5729-CA-Toronto-TechnicalSuppo.007
Not the right fit? Search for Technical Support Specialist, Alpha - $60,000/year USD jobs in Toronto, Ontario, Canada
About Crossover
Crossover is a global recruitment company, founded in 2014. We're the world's largest recruiter that specializes in elite full-time remote jobs, hiring the top 1% of tech talent from every corner of the planet.
We find awesome talent in overlooked places, by posting jobs all over the world, and giving everyone an equal opportunity to prove their skills are world-class. Our system of AI-powered assessments is based on objective factors that are scientifically proven to predict high performance (e.g. cognitive aptitude).
𝐇𝐄𝐋𝐏𝐅𝐔𝐋 𝐋𝐈𝐍𝐊𝐒: 🧑 Reviews from people we've hired: crossover.com/reviews 💼 Current openings: crossover.com/jobs 💎 Hire someone for your company: crossover.com/hire ♟️ How the process works: crossover.com/selection-process ❓ FAQs: crossover.com/help
𝑵𝒐𝒕𝒆: Crossover jobs are are fully compliant with LinkedIn's policies, as well as the applicable laws in every country where we advertise.
Allow us to clarify some common misconceptions:
1) The reason we post so many job ads is because LinkedIn organizes all job postings by location. So, the only way to reach candidates all over the world is to post multiple ads in every city you want to hire from. Most recruiters don't bother because it's too time consuming... but we're not most recruiters.
2) We mostly recruit independent contractors, not employees, because labor laws vary so much from one country to another that it's near-impossible to recruit globally otherwise (which is why it's still uncommon even though most jobs can now be done remotely).
3) As is standard for any self-employed person, the stated pay is the entire compensation package. Because they are not employees, each contractor is responsible for handling the things that an employer would take care of e.g. taxes, equipment, vacation time, health insurance. One of the major reasons that Crossover jobs pay so much more than local jobs is to overcompensate for these costs.
It's hard, but it's worth it!
Similar Jobs
Technical Support Specialist, Alpha (Remote) - $60,000/year USD
About the role
A student is ready to learn, but the app refuses to load. A guide's dashboard displays incorrect mastery scores. L1 support and the AI have already attempted resolution without success. The issue is now yours — and a child's learning day depends on you identifying what has actually gone wrong.
The majority of your workday will involve tickets that no one else managed to resolve, spanning the diverse applications that comprise Alpha's learning platform. You will replicate the issue in a setup that matches the student's or guide's environment, examine logs and documentation, leverage AI to accelerate your work, and then validate everything it produces, because an incorrect answer delivered to a classroom scales its impact rapidly. Ramping up on a new product nearly every week is expected. This is the nature of the role, not a caution.
Each problem is yours from start to finish: replicate it, identify the underlying cause, and resolve it with the fewest interactions necessary to restore the student or guide's workflow. The documentation you create strengthens the next agent and the next AI system, ensuring your solution continues to add value well beyond your current ticket. In time, you will become the go-to resource the team relies on for its most challenging education-product issues.
If you seek the difficult, unclear problem, and you genuinely care that the product ultimately helps a child learn, submit your application.
What You Will Be Doing
Address unclear, escalated support requests from students, parents, and guides that AI and L1 could not resolve. Replicate issues in environments mirroring the user's device, application, and setup, using logs and actual data. Conduct thorough investigations across Alpha's learning applications (tickets, Slack, knowledge repositories, logs) prior to escalating. Use AI tools (such as ChatGPT or Claude) to accelerate diagnosis, anchor them in authentic documentation, and validate all outputs. Engage clearly and professionally with non-technical users, collecting sufficient information upfront to enable single-pass resolution. Escalate issues to engineering with comprehensive diagnostic context when a genuine product defect is confirmed. Record your diagnostic reasoning so future team members and AI workflows can leverage it.
What You Won’t Be Doing
Working from scripts or decision trees for a single product. Managing the simple queue. AI already handles tickets solvable through knowledge-base searches. Escalating difficult problems to engineering without first replicating and isolating them. Allowing AI to do your thinking, or delivering its responses without verification. Waiting for direction, or relying on others to remove blockers.
Technical Support Specialist Key Responsibilities
Diagnose and resolve complex, ambiguous customer issues to their root cause across Alpha's education products.
Basic Requirements
2+ years in a hands-on technical role such as technical support, software engineering, QA, sysadmin, or DevOps. Your job title does not have to be "support." Comfortable constructing and reading REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating in command line and log environments. Practical experience using AI tools (such as ChatGPT or Claude) in daily technical work. Professional fluency in written and spoken English. Available to work full-time (40 hours/week), with all working hours between 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern).
Nice-to-have Requirements
Experience supporting non-technical end users (in education, edtech, or consumer applications), not only IT professionals. Practical experience guiding AI tools and identifying their errors. A proven history of troubleshooting across multiple unrelated products, not a single one. Developer-level proficiency: capable of reading code or tracing an API call when necessary.
About Alpha
Join the team building school around student growth
Alpha reimagines the school day around faster learning, stronger mentorship, and more time for students to build real-world skills.
Roles with real student impact: Alpha hires teachers (guides), operators, admissions experts, school & curriculum leaders, and remote team members.
Education work that pays like it matters: Alpha offers six-figure roles for people ready to help build a radically better school experience.
A culture built for builders: Alpha is fast-moving, ambitious, and student focused. It’s for people who want to improve the system, not maintain it.
Alpha is where you can do the most meaningful work of your career.
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 $30 USD/hour, which equates to $60,000 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-5729-CA-Toronto-TechnicalSuppo.007
Not the right fit? Search for Technical Support Specialist, Alpha - $60,000/year USD jobs in Toronto, Ontario, Canada
About Crossover
Crossover is a global recruitment company, founded in 2014. We're the world's largest recruiter that specializes in elite full-time remote jobs, hiring the top 1% of tech talent from every corner of the planet.
We find awesome talent in overlooked places, by posting jobs all over the world, and giving everyone an equal opportunity to prove their skills are world-class. Our system of AI-powered assessments is based on objective factors that are scientifically proven to predict high performance (e.g. cognitive aptitude).
𝐇𝐄𝐋𝐏𝐅𝐔𝐋 𝐋𝐈𝐍𝐊𝐒: 🧑 Reviews from people we've hired: crossover.com/reviews 💼 Current openings: crossover.com/jobs 💎 Hire someone for your company: crossover.com/hire ♟️ How the process works: crossover.com/selection-process ❓ FAQs: crossover.com/help
𝑵𝒐𝒕𝒆: Crossover jobs are are fully compliant with LinkedIn's policies, as well as the applicable laws in every country where we advertise.
Allow us to clarify some common misconceptions:
1) The reason we post so many job ads is because LinkedIn organizes all job postings by location. So, the only way to reach candidates all over the world is to post multiple ads in every city you want to hire from. Most recruiters don't bother because it's too time consuming... but we're not most recruiters.
2) We mostly recruit independent contractors, not employees, because labor laws vary so much from one country to another that it's near-impossible to recruit globally otherwise (which is why it's still uncommon even though most jobs can now be done remotely).
3) As is standard for any self-employed person, the stated pay is the entire compensation package. Because they are not employees, each contractor is responsible for handling the things that an employer would take care of e.g. taxes, equipment, vacation time, health insurance. One of the major reasons that Crossover jobs pay so much more than local jobs is to overcompensate for these costs.
It's hard, but it's worth it!