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Senior Technical Support Analyst, Trilogy; Remote

Remote / Online - Candidates ideally in
Toronto, Ontario, C6A, Canada
Listing for: Crossover
Full Time, Remote/Work from Home position
Listed on 2026-01-12
Job specializations:
  • IT/Tech
    IT Support, Technical Support
Salary/Wage Range or Industry Benchmark: 60000 CAD Yearly CAD 60000.00 YEAR
Job Description & How to Apply Below
Position: Senior Technical Support Analyst, Trilogy (Remote) - $60,000/year USD

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

Join to apply for the Senior Technical Support Analyst, Trilogy (Remote) - $60,000/year USD role at Crossover.

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

Base pay range

$30.00/hr - $30.00/hr

The support sector is overwhelmed by escalating complexity even as customer demands intensify. Today's customers anticipate AI-driven, immediate responses, yet most companies remain stuck in experimental phases, unable to convert AI into tangible results. The challenge will only deepen. Industry forecasts suggest that by 2029, agentic systems will independently handle the majority of routine inquiries, creating a widening chasm between what customers expect and what current operations can deliver.

AI-Augmented

Customer Resolutions
  • Examine escalated, complex tickets that have bypassed AI systems, deploy human judgment where AI capabilities fall short, and subsequently enhance the AI system to bridge those gaps
What you won’t be doing
  • Spending two full months ramping up; you are expected to become proficient across multiple products in your first month (we acknowledge this pace is demanding)
  • Leaning on your manager for assistance; if you cannot skillfully unblock yourself, this role will present significant challenges
Senior Technical Support Analyst

Key Responsibilities
  • Combine advanced human technical expertise with AI-powered tools to deliver superior customer support, concentrating on sophisticated issues that AI systems are not yet capable of resolving independently
Basic Requirements
  • Must be located in North or South America
  • Minimum of 3 years total experience in technical customer support roles
  • Advanced proficiency with generative AI (i.e., hands‑on use 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 standard
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.

Crossover Job Code: LJ-3330-CA-Nunavut-Senior Technica.
016

Seniority level

Associate

Employment type

Full-time

Job function

Business Development, Information Technology, and Customer Service

Industries

Computer Hardware Manufacturing, Software Development, and IT Services and IT Consulting

Referrals increase your chances of interviewing at Crossover by 2x

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Position Requirements
10+ Years work experience
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