Principal Technical Support Engineer, Trilogy; Remote

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

1 day ago Be among the first 25 applicants

This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

$30.00/hr - $30.00/hr

Customer expectations in support are rising sharply while organizational complexity continues to deepen. Today's customers anticipate immediate, AI-driven resolutions, yet most companies remain stuck in pilot phases and fail to translate AI into measurable results. The bar is about to rise even further. Agentic systems are expected to autonomously handle the majority of routine issues by 2029, creating a widening chasm between what customers demand and what most support teams can deliver.

We are bridging that divide through a fundamentally different approach: AI-augmented "cyborg" agents who combine advanced troubleshooting expertise with product knowledge and agentic AI capabilities. In this position, you will train, refine, and mentor the tools themselves. Each problem you resolve strengthens our automation frameworks, every root cause investigation becomes a repeatable procedure, and every edge case you decode enhances the system for thousands of future customers.

This is the intersection of sophisticated troubleshooting, human judgment, and AI orchestration—delivering rapid resolutions now while building compounding intelligence for the future.

This position demands hands-on problem solving at production scale. You will diagnose ambiguous failures spanning networks, databases, cloud infrastructure, and enterprise applications; use AI to generate hypotheses, execute tests, and accelerate resolutions; capture the human reasoning that trains our systems; and proactively identify patterns that transform isolated fixes into lasting automations. This is not about following scripts, sorting tickets, or escalating to Level 3.

If you excel at lateral thinking when documentation is sparse, if you transition seamlessly from packet captures to query plans to workflow traces, and if you are confident correcting an LLM when it errs, you will thrive here.

• Investigate complex tickets escalated by AI systems, apply specialized human judgment where AI is insufficient, and subsequently enhance the AI system to close those gaps.

• Spending two full months onboarding; you will be expected to achieve proficiency across multiple products within the first month (we recognize this is demanding).
• Depending on your managers for assistance; if you lack the ability to unblock yourself independently, this role will present significant challenges.

• Combine technical human judgment and AI capabilities to provide outstanding customer support, concentrating on sophisticated issues that AI cannot yet independently resolve.

• Must be located in North or South America.
• At least 3 total years of experience in a technical customer support role.
• Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you have only used LLMs for research, learning, brainstorming, or content generation, that will be deemed insufficient.

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.

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-Toronto-Principal Techn.
001

Seniority level:
Associate

Employment type:

Full-time
Job function:
Engineering, Information Technology, and Customer Service
Industries:
Computer Hardware Manufacturing, Software Development, and IT Services and IT Consulting