Technical Support Engineer, Trilogy (Remote) - $60,000/year USD

The toughest tickets do not require another person following scripts. They demand someone capable of stepping into unclear situations, misconfigured systems, conflicting evidence, upset customers, and AI-produced missteps—then determining what is genuinely broken. This position is designed for the support engineer drawn to unsolved problems: replicating failures, analyzing logs, tracking API behavior, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI rigorously without accepting its output uncritically.

Most support organizations still operate using queues, templates, handoffs, and documented workarounds. We are constructing something different. Standard support inquiries are increasingly managed by AI and L1 processes, meaning human expertise is allocated to the most complex challenges. AI is not replacing you in this role. It is the instrument you control, validate, challenge, and confirm.

This position is not about copying AI responses, making quick guesses, awaiting direction, or escalating whenever the issue becomes unfamiliar. It is not suited for someone who masters one product then stalls when the next ticket involves a different technology stack. It is about delivering the correct answer with the minimum number of customer interactions the situation permits: reproducing before proposing solutions, researching across tickets, Slack threads, knowledge bases, logs, configurations, and tangible evidence before escalating, and composing customer communications clear enough to calm the situation. The technical foundation is assumed: REST APIs, JSON, HTTP status codes, command line, and logs. That baseline grants you entry. Sound judgment amid uncertainty is what makes you effective.

In this position, your responsibility is to retain ownership of the issue until resolution or clean escalation, with diagnostic logic valuable enough for the subsequent agent and future AI workflows. You will thrive in this role if the ticket that defies explanation is the one you most want to solve. You will dislike it if you require one product, one documented process, and external help to move forward. If that type of challenge energizes you, please apply.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Resolving unclear, escalated tickets by merging thorough, practical troubleshooting with AI that you guide, anchor in actual documentation, and validate.
  
  

What You Won’t Be Doing

• Spending two full months learning the systems; you will need to become proficient with multiple products during the first month (we recognize this is demanding)
• Depending on your managers for assistance; if you cannot effectively remove your own blockers, you will probably find this role difficult
  
  

Technical Support Engineer Key Responsibilities

• Combine technical human judgment and AI tools to provide outstanding customer support, concentrating on complicated issues that AI cannot yet independently resolve
  
  

Basic Requirements

• 2+ years in a practical technical position such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The job title does not have to be "support."
• Proficient with constructing and reading REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating in a command line (CLI) and logs.
• Practical experience applying generative AI tools (such as ChatGPT or Claude) in your regular technical work.
• Professional fluency in English, both written and spoken.
• Available to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)
  
  

Nice-to-have Requirements

• Background supporting technical or business customers using enterprise software or B2B SaaS, beyond internal IT.
• API troubleshooting using tools like Postman or curl.
• Demonstrated ability troubleshooting across multiple unrelated products or technology stacks, not only one.
• Developer-level depth: you can interpret code or follow an API call when the situation requires it.
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, innovating new technology, and incubating new businesses.

Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack.

Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career in leaps and bounds.

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-3330-AE-AbuDhabi-TechnicalSuppo.130