The toughest tickets do not require another person following a script. They require someone capable of stepping into unclear situations, misconfigured systems, conflicting evidence, upset customers, and AI-produced false leads—then determining what is genuinely broken. This position is designed for the support engineer drawn to the unresolved problem: reproducing the error, examining logs, tracking API behavior, analyzing JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI rigorously without accepting its output uncritically.
Most support organizations continue to rely on ticket queues, templated responses, hand-offs, and documented issue repositories. We are constructing a different model. Standard support is progressively managed by AI and L1 processes, meaning human expertise is allocated to the hardest challenges. AI is not replacing you in this role. It is the instrument you control, validate, test, and confirm.
This position is not about copying AI-generated replies, making rapid guesses, awaiting direction, or escalating the instant an issue becomes unfamiliar. It is not suited for someone who masters one product and stalls when the following ticket involves a different technology. It is about delivering the correct answer in the minimum number of customer interactions the situation permits: reproducing before proposing solutions, investigating across tickets, Slack threads, knowledge bases, logs, configurations, and actual artifacts before escalating, and composing customer communications clear enough to defuse tension. The technical foundation is assumed: REST APIs, JSON, HTTP status codes, command line, and logs. That establishes your baseline. 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 the next AI process. You will find this role rewarding if the ticket that defies logic is the one you prefer. You will find it unsuitable if you require a single product, a single playbook, and external assistance to proceed. If that type of challenge energizes you, please apply.
What You Will Be Doing
AI-Augmented Customer Resolutions: Unclear, escalated tickets resolved through deep, direct troubleshooting combined with AI that you guide, anchor in verified documentation, and validate.
What You Won’t Be Doing
Spending two full months on onboarding; you will be required to learn multiple products within the first month (we recognize this is demanding) Depending on your managers for assistance; if you are not skilled at removing your own blockers, you will probably find this role difficult
Technical Support Engineer Key Responsibilities
Combine technical human judgment and AI tools to provide superior customer support, concentrating on complicated issues that AI cannot yet independently resolve
Basic Requirements
2+ years in a technical, hands-on position such as technical support, customer support engineering, software engineering, QA, or sysadmin/Dev Ops. The job title does not need to include "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 a command line (CLI) and logs. Practical experience applying generative AI tools (such as Chat GPT or Claude) in your regular technical work. Professional fluency in English, both written and spoken. Able to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)
Nice-to-have Requirements
Experience supporting technical or business customers on enterprise software or B2B Saa S, not only internal IT. API troubleshooting using tools like Postman or curl. A history of troubleshooting across multiple unrelated products or technology stacks, not just one. Developer-level depth: you can read code or trace 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-COUNTRY-Technical Suppo.001
Skills: Troubleshooting, Technical Support, Networking, Windows, Windows Server, Internet Protocol Suite (TCP/IP), Computer Hardware, Operating Systems, Servers