The difficult tickets require more than someone who can follow a script. They demand an engineer capable of navigating unclear context, misconfigured systems, conflicting evidence, upset customers, and AI-generated noise—then determining what actually went wrong. This position is designed for the support engineer drawn to the unsolved problem: replicating the issue, analyzing logs, tracking API behavior, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI aggressively without blind trust.<br><br>Most support organizations still operate on queues, macros, handoffs, and "known issue" documentation. We are constructing something different. Routine inquiries are increasingly managed by AI and L1 processes, which reserves human judgment for the hardest challenges. AI is not your competitor in this role. It is the instrument you control, validate, test, and confirm.<br><br>This position is not about copying AI responses, making hasty guesses, waiting for direction, or escalating the instant an issue becomes unfamiliar. It is not suited for someone who specializes deeply in one product and struggles when the following ticket involves a different technology stack. It is about delivering the correct answer with the minimum customer interactions the problem permits: replicating before proposing solutions, investigating across tickets, Slack threads, knowledge bases, logs, configurations, and tangible evidence before escalating, and composing customer communications clear enough to defuse tension. The technical fundamentals are assumed: REST APIs, JSON, HTTP status codes, command line, and logs. Those are entry requirements. Sound judgment amid ambiguity is what makes you effective.<br><br>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 subsequent AI workflow. You will thrive in this role if the ticket that defies explanation is the one you prefer most. You will dislike it if you require one product, one procedure, and someone else to remove obstacles. If that type of pressure focuses you, please apply.<br><br><strong>What You Will Be Doing<br><br></strong><ul><li>AI-Augmented Customer Resolutions: Resolve ambiguous, escalated tickets by integrating thorough, hands-on troubleshooting with AI that you guide, anchor in authentic documentation, and validate.<br><br></li></ul><strong>What You Won’t Be Doing<br><br></strong><ul><li>Spending two full months on onboarding; you will be expected to become proficient with one or more products within the first month (we recognize this is demanding)</li><li>Depending on your managers for assistance; if you are not skilled at removing your own blockers, you will likely find this role challenging<br><br></li></ul><strong>Application Support Engineer Key Responsibilities<br><br></strong><ul><li>Combine technical human judgment and AI capabilities to provide outstanding customer support, concentrating on sophisticated issues that AI cannot yet independently resolve<br><br></li></ul><strong>Basic Requirements<br><br></strong><ul><li>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."</li><li>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.</li><li>Hands-on experience using generative AI tools (such as ChatGPT or Claude) in your daily technical work.</li><li>Professional fluency in English, written and spoken.</li><li>Able to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)<br><br></li></ul><strong>Nice-to-have Requirements<br><br></strong><ul><li>Experience supporting technical or business customers on enterprise software or B2B SaaS, not just internal IT.</li><li>API troubleshooting with tools like Postman or curl.</li><li>A track record of troubleshooting across several unrelated products or tech stacks, not just one.</li><li>Developer-grade depth: you can read code or trace an API call when the problem demands it.<br><br></li></ul><strong>About Trilogy<br><br></strong>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.<br><br>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.<br><br>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.<br><br>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!<br><br><strong>Working with us<br><br></strong>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.<br><br>Crossover Job Code: LJ-3330-CA-Vancouve-ApplicationSup.017<br><br>