Complex support tickets require more than someone who follows scripts. They demand an engineer capable of navigating unclear context, misconfigured systems, conflicting evidence, upset customers, and AI-generated false leads—then determining the actual root cause. This position is designed for the support engineer drawn to unsolved problems: replicating the failure, analyzing logs, tracing API behavior, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI aggressively while maintaining critical skepticism.

Traditional support structures still rely on ticket queues, canned responses, handoff protocols, and documented workarounds. We are constructing something fundamentally different. As AI and L1 processes absorb routine inquiries, human expertise becomes concentrated on the hardest challenges. AI does not replace you in this environment. It serves as the instrument you control, validate, challenge, and confirm.

This position is not about copying AI-generated answers, making rushed guesses, waiting for direction, or escalating immediately when the issue becomes unfamiliar. It is not suited for someone with deep knowledge of a single product who freezes when the next case involves a different technology stack. It requires delivering accurate resolutions with minimal back-and-forth: reproducing issues before proposing fixes, cross-referencing tickets, Slack threads, knowledge bases, logs, configurations, and tangible evidence before escalation, and composing customer communications that are clear enough to defuse tension. The technical foundation is non-negotiable: REST APIs, JSON, HTTP status codes, command line proficiency, and log analysis. That earns entry. Sound judgment amid uncertainty is what makes you effective.

In this position, you own each issue until resolution or a well-documented handoff, providing diagnostic insights valuable to the next engineer and future AI workflows. You will thrive here if the ticket that defies explanation is the one you most want to solve. You will struggle if you require a single product focus, a fixed playbook, and external intervention to move forward. If that environment energizes you, we encourage you to apply.

What You Will Be Doing

AI-Augmented Customer Resolutions: Resolving ambiguous, escalated cases by combining rigorous, hands-on technical investigation with AI tools that you guide, validate against real documentation, and confirm before deployment.

What You Won’t Be Doing

Spending two full months onboarding; you are expected to become effective across multiple products within the first month (we recognize this pace is demanding) Depending on managers for assistance; self-sufficiency in problem-solving is essential—without it, this role will be difficult

Technical Support Engineer Key Responsibilities

Combine technical human judgment with AI-driven workflows to provide outstanding customer support, particularly on complex problems that AI cannot independently resolve

Basic Requirements

2+ years in a technical role involving hands-on problem-solving, including technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The formal title need not be "support." Proficient in constructing and interpreting REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and navigating command line interfaces (CLI) and logs. Practical experience using generative AI tools (such as ChatGPT or Claude) as part of your regular technical workflow. Professional-level English fluency, both written and verbal. Available to work a complete 40-hour week during US business hours (Eastern Time). This is a full daytime shift aligned with US hours, which may require overnight availability in certain time zones. Located in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines (relocation assistance is not provided).

Nice-to-have Requirements

Background supporting technical or business users on enterprise software or B2B SaaS platforms, beyond internal IT support. API debugging experience using tools like Postman or curl. Demonstrated ability troubleshooting across multiple unrelated products or technology stacks, not limited to a single domain. Developer-level capability: able to read code or trace an API request 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 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-TechnicalSuppo.147