Technical Support Engineer, Trilogy (Remote) – $60,000/Year Usd

November 4, 2025

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Job Description

In a world where standard customer support often drowns in redundancy and mediocrity, Trilogy stands apart. Our AI-driven approach to managing over 100 enterprise software products ensures that the challenges you face are never mundane, always requiring your top-tier problem-solving skills.

What You Will Be Doing

  • AI-Augmented Customer Resolutions: Dive deep into complex tickets escalated by AI systems, infuse them with human expertise, and enhance the AI’s capabilities to bridge existing gaps.

What You Won’t Be Doing

  • Spending months to get acclimated; expect to master several products within the first month, as we set a fast-paced learning environment.
  • Relying heavily on managerial support; independence and self-sufficiency are key to thriving in this role.

Technical Support Engineer Key Responsibilities

  • Leverage your technical expertise alongside AI capabilities to deliver top-notch customer support by addressing complex issues that AI alone cannot resolve.

Basic Requirements

  • A minimum of 3 years in a technical customer support position.
  • Proficiency in advanced generative AI tools, including workflow automation and custom GPTs; mere experience with LLMs for basic tasks will not suffice.
  • Residency in North or South America.

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-Toronto-TechnicalSuppo.161