Technical Support Engineer, Trilogy (Remote) - $60,000/year USD

Crossover; Vancouver; On-site; CAD 75,000 - 92,000; Full time

Job summary

Trilogy is seeking a Technical Support Engineer for a full-time contractor role via Crossover. The position focuses on complex problem solving using AI-guided troubleshooting, REST APIs, JSON payload analysis, and exhaustive evidence across tickets and logs.

You will own cases end-to-end, including escalation when necessary. Requirements include 2+ years in a technical role, strong English, and availability 1:00 PM–10:00 PM UTC.

Qualifications

• Proficient in constructing and interpreting REST API calls and JSON payloads.
• Understanding HTTP status codes (e.g., 401, 404, 429) and CLI/logs.
• Practical experience applying generative AI tools in technical work.
• Professional fluency in English, written and spoken.

Responsibilities

• Provide AI-augmented customer resolutions for unclear, escalated cases.
• Own issues from intake to resolution or escalation with thorough diagnostics.

Skills

REST API calls

JSON

HTTP status codes

CLI/logs

Generative AI tools

English fluency

Full-time availability

Tools

Postman

curl

Job description

The toughest tickets do not require another person following scripts. They require someone capable of stepping into uncertain situations, misconfigured systems, conflicting evidence, upset customers, and AI-generated noise—then determining what is truly broken. This position is designed for the support engineer who gravitates toward the unresolved problem: replicating the issue, analyzing logs, tracking API interactions, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI aggressively without accepting its output uncritically.

Most support organizations still operate on queues, templates, handoffs, and "known issue" documentation. We are creating something different. Standard support inquiries are increasingly managed by AI and L1 processes, which means human expertise is dedicated to the most complex issues. AI is not here to replace you. It is the instrument you guide, validate, challenge, and confirm.

This position is not about copying AI-generated responses, making hasty guesses, awaiting directives, or escalating immediately when the problem becomes unfamiliar. It is not intended for someone who masters one product and falters when the next case involves a different technology stack. It is about delivering the correct answer with the minimum number of customer interactions the issue permits: reproducing before proposing solutions, researching across tickets, Slack, knowledge bases, logs, configurations, and actual evidence 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 provides entry. Judgment amid uncertainty is what makes you effective.

In this position, your responsibility is to take 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 thrive in this role if the ticket that refuses to yield clarity is the one you most want to solve. You will dislike it if you require a single product, a single playbook, and others to remove obstacles.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Unclear, escalated cases resolved through deep, practical troubleshooting combined with AI that you control, anchor in actual 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 difficult

Technical Support Engineer Key Responsibilities

• Combine technical human judgment and AI tools to provide outstanding customer support, concentrating on complicated problems that AI cannot yet independently resolve

Basic Requirements

• 2+ years in a practical technical position such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The job title does not need to include "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 operating in a command line (CLI) and logs.
• Practical experience applying generative AI tools (such as ChatGPT or Claude) in your routine technical work.
• Professional fluency in English, both written and spoken.
• Available to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)

Nice-to-have Requirements

• Background supporting technical or business customers on enterprise software or B2B SaaS, beyond internal IT.
• API troubleshooting using tools like Postman or curl.
• A history of troubleshooting across multiple distinct products or tech stacks, not only one.
• Developer-level depth: you can interpret 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.

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.