Senior Technical Support Engineer, Trilogy (Remote) - $60,000/year USD - #443347
Trilogy
Date: 1 day ago
City: Winnipeg, MB
Contract type: Full time
Remote

In most companies, traditional customer support is often plagued by inefficiency and mediocrity. Support engineers frequently waste time on repetitive tasks or struggle with problems outside their narrow expertise. Data shows that over 60% of tickets get escalated because the first line of defense lacks the skills or knowledge to resolve them.
At Trilogy, we don't do traditional. Managing over 100 enterprise software products, we've redefined customer support with advanced AI. Most issues are handled by our AI-powered chatbot, leaving only the most complex challenges for our engineers. That means every ticket you touch is difficult, varied, and requires creative problem-solving.
In this role, there's no time for hand-holding or "learning the ropes" at a leisurely pace. If you need constant guidance, struggle to self-learn, or tend to ask obvious questions, you won't last two weeks. Success requires a proactive mindset, the ability to adapt quickly, and the drive to figure things out independently.
If you're ready to step up and tackle the toughest problems in customer support, this role will accelerate your growth like nothing else. You'll gain unparalleled technical expertise across a massive product portfolio while contributing directly to Trilogy's reputation for excellence. If you are up to the task of pushing your limits, we'd love to see you apply.
What You Will Be Doing
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-Winnipeg-SeniorTechnica1
At Trilogy, we don't do traditional. Managing over 100 enterprise software products, we've redefined customer support with advanced AI. Most issues are handled by our AI-powered chatbot, leaving only the most complex challenges for our engineers. That means every ticket you touch is difficult, varied, and requires creative problem-solving.
In this role, there's no time for hand-holding or "learning the ropes" at a leisurely pace. If you need constant guidance, struggle to self-learn, or tend to ask obvious questions, you won't last two weeks. Success requires a proactive mindset, the ability to adapt quickly, and the drive to figure things out independently.
If you're ready to step up and tackle the toughest problems in customer support, this role will accelerate your growth like nothing else. You'll gain unparalleled technical expertise across a massive product portfolio while contributing directly to Trilogy's reputation for excellence. If you are up to the task of pushing your limits, we'd love to see you apply.
What You Will Be Doing
- AI-Augmented Customer Resolutions: Analyze complex tickets escalated by AI systems, apply human expertise to areas where AI falls short, and then close the gap by improving the AI system
- Taking two whole months to get up to speed; you will be expected to ramp up one several products within the first month (we are aware this is aggressive)
- Relying on your managers for help; if you are not adept at unblocking yourself, you will likely struggle in this role
- Integrate technical human expertise and AI capabilities to deliver exceptional customer support, focusing on complex issues that AI cannot yet fully resolve
- Currently based in North or South America
- At least 4 total years of experience in a technical customer support or engineering role
- Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you've 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.
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-Winnipeg-SeniorTechnica1
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