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Technical Support Engineer, Trilogy; Remote

Remote / Online - Candidates ideally in
Toronto, Ontario, C6A, Canada
Listing for: Crossover
Full Time, Remote/Work from Home position
Listed on 2026-01-28
Job specializations:
  • IT/Tech
    Technical Support, IT Support, AI Engineer
Salary/Wage Range or Industry Benchmark: 60000 CAD Yearly CAD 60000.00 YEAR
Job Description & How to Apply Below
Position: Technical Support Engineer, Trilogy (Remote) - $60,000/year USD

Overview

Customer expectations for support are rising sharply while the industry struggles with mounting complexity. Today's customers anticipate AI-driven, immediate resolutions, yet most companies remain stuck in pilot phases, unable to convert AI into tangible results. The challenge will intensify further. Industry projections indicate that by 2029, agentic systems will autonomously handle the majority of routine issues, creating a widening chasm between what customers expect and what organizations currently deliver.

What

You Will Be Doing
  • AI-Enhanced Issue Resolution:
    Investigate complex escalations that AI systems cannot fully address, apply specialized human judgment to bridge capability gaps, and subsequently refine the AI system to close those gaps
What You Won’t Be Doing
  • Taking a leisurely two-month onboarding period; you are expected to achieve proficiency across multiple products within your first month (we recognize this timeline is demanding)
  • Depending on managers to clear obstacles; if you cannot effectively unblock yourself, this role will present significant challenges
Technical Support Engineer

Key Responsibilities
  • Combine human technical expertise with AI capabilities to provide superior customer support, concentrating on sophisticated problems that remain beyond current AI resolution capacity
Basic Requirements
  • Must be located in North or South America
  • Minimum 3 years total experience in technical customer support positions
  • Foundational coding ability sufficient for troubleshooting and implementing bug fixes
  • Advanced proficiency with generative AI tools (i.e., working knowledge of multiple AI platforms, capability to automate workflows and build custom GPTs); experience limited to using LLMs for research, learning, brainstorming, or content creation will not meet this requirement
  • Troubleshooting Expertise:
    Ability to translate complex technical issues into accessible language, demonstrate thorough problem comprehension, suggest appropriate diagnostic approaches, identify multiple resolution pathways, and exhibit meticulous attention to detail
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.

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  for more details on this topic.

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