Complex support cases don't require another person following scripts. They demand someone capable of navigating unclear situations, misconfigured systems, conflicting evidence, upset clients, and unhelpful AI outputs—then determining the actual problem. This position suits the support engineer drawn to unresolved issues: recreating failures, analyzing logs, tracking API responses, examining JSON structures, distinguishing between 401, 404, and 429 errors, and leveraging AI rigorously without blind reliance.

Traditional support operations remain organized around ticket queues, templated responses, transfer protocols, and documented issue libraries. Our approach differs fundamentally. Standard support increasingly falls to AI and first-tier processes, leaving human expertise for the hardest challenges. AI isn't replacing you in this context—it's an instrument you command, validate, test, and confirm.

This position isn't about copying AI-generated solutions, making hasty guesses, awaiting direction, or escalating whenever unfamiliarity surfaces. It isn't suitable for those who master one product then stall when the next ticket involves different technology. It centers on delivering accurate answers with minimal customer interaction: reproducing issues before proposing fixes, researching across tickets, internal channels, knowledge repositories, logs, configurations, and tangible evidence before escalation, and composing customer communications clear enough to defuse tension. The technical foundation is assumed: REST APIs, JSON, HTTP response codes, command-line tools, and log analysis. That foundation grants entry. Sound judgment amid uncertainty creates impact.

Your responsibility is maintaining ownership of each issue until resolution or clean escalation, providing diagnostic logic valuable to subsequent agents and future AI processes. You'll thrive here if the inexplicable ticket is your preferred challenge. You'll struggle if you require single-product focus, rigid procedures, and external help to progress. If that environment energizes you, we encourage your application.

What You Will Be Doing

AI-Enhanced Issue Resolution: Resolving ambiguous, escalated customer cases through intensive, practical troubleshooting paired with AI systems you control, anchor to authentic documentation, and validate thoroughly.

What You Won’t Be Doing

Spending two full months on onboarding; you'll need to become proficient across multiple products within your first month (we recognize this expectation is demanding) Depending on management for assistance; if self-directed problem-solving isn't your strength, this role will present difficulties

Application Support Engineer Key Responsibilities

Combine advanced technical human judgment with AI tools to provide outstanding customer support, concentrating on complicated problems that AI cannot yet independently solve

Basic Requirements

2+ years in a technical capacity including technical support, customer support engineering, software engineering, QA, or systems administration/DevOps. "Support" need not appear in your job title. Proficient in creating and analyzing REST API requests and JSON responses, understanding HTTP status codes (distinguishing 401 from 404 and 429 from 403), and operating within command-line interfaces (CLI) and log files. Practical experience applying generative AI platforms (such as ChatGPT or Claude) to everyday technical tasks. Professional-level English fluency in both written and verbal communication. Available to work a complete 40-hour week aligned with US business hours (Eastern Time). This constitutes a full US-daytime schedule, resulting in overnight hours in certain regions. Located in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines (relocation assistance not provided).

Nice-to-have Requirements

Background supporting technical or business clients using enterprise software or B2B SaaS products, beyond internal IT support. API diagnostics using tools such as Postman or curl. Demonstrated ability troubleshooting multiple unrelated products or technology stacks, rather than specializing in one. Developer-level capability: comfortable reading source code or tracing API transactions when circumstances require 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 by 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-CA-Ottawa-ApplicationSup.026