The most difficult tickets do not require another script reader. They require someone capable of stepping into unclear situations, misconfigured systems, conflicting evidence, upset customers, and AI-generated noise, and then determining what is genuinely broken. This position is designed for the support engineer who prefers the unsolved problem: replicating the error, analyzing logs, tracking API calls, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI aggressively without placing blind trust in it. The majority of support organizations still operate around ticket queues, templated responses, handoffs, and playbooks for known issues. We are constructing the alternative. Routine support is progressively managed by AI and L1 processes, which means human intelligence is allocated to the hardest problems. AI is not replacing you in this role. It is the instrument you command, validate, challenge, and confirm. This position does not involve copying AI-generated responses, making rapid guesses, awaiting direction, or escalating the instant the issue becomes unfamiliar. It is not suited for someone who masters one product and stalls when the subsequent ticket involves a different technology stack. It is about delivering the correct answer in the minimum number of customer interactions the problem requires: reproducing before proposing solutions, investigating across tickets, Slack channels, knowledge bases, logs, configurations, and actual evidence before escalating, and composing customer communications clear enough to resolve tension. The technical foundation is assumed: REST APIs, JSON, HTTP status codes, command line interface, and log analysis. That qualifies you for entry. Sound judgment amid uncertainty is what makes you effective. In this position, your responsibility is to maintain ownership of the issue until it is either resolved or escalated cleanly, with diagnostic logic valuable enough for the subsequent agent and the next AI workflow. You will thrive in this role if the ticket that defies explanation is the one you prefer most. You will find it unsuitable if you require a single product, a single playbook, and external support to proceed. If that type of challenge motivates you, please apply. What You Will Be Doing - AI-Augmented Customer Resolutions: Complex, escalated tickets addressed through deep, practical troubleshooting combined with AI that you control, anchor in authentic documentation, and validate. What You Won’t Be Doing - Spending two full months learning the systems; you will be required to become proficient with 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 challenging Application Support Engineer Key Responsibilities - Combine technical human judgment and AI capabilities to provide outstanding customer support, concentrating on complicated issues that AI cannot yet completely address Basic Requirements - 2+ years in a hands-on technical role such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The title does not need to be "support." - Comfortable making and reading REST API calls and JSON, interpreting HTTP status codes (such as 401 vs 404 and 429 vs 403), and working in a command line (CLI) and logs. - Hands-on experience using generative AI tools (such as ChatGPT or Claude) in your daily technical work. - Professional fluency in English, 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 SaaS, not just internal IT. - API troubleshooting with tools like Postman or curl. - A track record of troubleshooting across several unrelated products or tech stacks, not just one. - Developer-grade depth: you can read code or trace an API call when the problem demands 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-PH-MetroCeb-ApplicationSup.007