Technical Support Engineer, Trilogy; Remote

You thrive when faced with difficult challenges. The unusual outliers. The support cases where documentation fails, metrics contradict each other, and colleagues have no answers. AI, systems, software, and diagnostic work excite you, but you have no interest in processing endless repetitive issues that automation should have eliminated long ago.

We're building AI‑enhanced "cyborg" specialists: professionals who combine advanced technical diagnostics with product knowledge and agentic AI capabilities. In this position, you determine which technical problems deserve human analysis, which should never need human intervention again, and how to convert today's most challenging cases into tomorrow's automated solutions. AI is your constant collaborator: you refine it, direct it, program it, and train it to shoulder more responsibility.

Each intricate failure you resolve transforms into a reusable prompt, process, or automation. Each underlying cause you identify strengthens the platform. Rather than addressing identical problems repeatedly, you concentrate on challenges that existing AI cannot yet manage, then eliminate that limitation. The outcome is reduced routine inquiries, accelerated resolutions, and a support infrastructure that scales your knowledge exponentially.

This represents a rare chance to develop AI proficiency without processing routine tickets daily. If you enjoy unconventional thinking when solutions aren't apparent, transitioning seamlessly from packet analysis to execution plans to workflow diagnostics, and explaining to an LLM precisely where it erred, this environment will suit you well.

• AI‑Enhanced Customer Problem Solving:
  Examine complex cases escalated by AI platforms, deploy human judgment in areas where AI proves insufficient, then eliminate that gap by enhancing the AI infrastructure.

• Spending two full months onboarding; you will need to achieve proficiency with multiple products during your first month (we recognize this expectation is demanding).
• Depending on management for assistance; if you cannot effectively remove your own obstacles, this role will present significant difficulties.

• Combine technical human judgment and AI functionality to provide outstanding customer support, concentrating on sophisticated issues that AI cannot yet completely address.

• Must be based in North or South America.
• At least 3 total years of experience in a technical customer support role.
• Basic coding skills for the purpose of troubleshooting/bug fixes.
• Troubleshooting
  
  Skills:
  
  Explaining complex issues in simple terms, demonstrating strong problem understanding, recommending relevant troubleshooting strategies, proposing multiple solution paths, and showing attention to detail.

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!

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  for more details on this topic.

Crossover Job Code: LJ-3330-CA-Ottawa-Technical Suppo.
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