Technical Support Engineer, Trilogy (Remote) - $60,000/year USD
CrossoverCanada1 day ago
Full-timeRemote FriendlyEngineering, Information Technology +1
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The support sector faces mounting complexity even as customer demands escalate. Today's customers anticipate AI-driven, immediate resolutions, yet most companies remain stuck in pilot phases and fail to translate AI into tangible results. Meanwhile, the benchmark is poised to rise further. By 2029, agentic systems are expected to autonomously handle the majority of routine issues, creating a critical divide between what customers expect and what organizations currently deliver.
We're bridging that divide through an alternative approach: AI-enhanced "cyborg" agents who combine extensive troubleshooting expertise with product knowledge and agentic AI. In this position, you refine, repair, and guide the tools. Each repair strengthens our automation, each root cause investigation becomes a repeatable blueprint, and each edge case you resolve enhances the system for thousands of future customers. This is the intersection of sophisticated troubleshooting, human insight, and AI coordination, delivering quicker resolutions now while building cumulative intelligence for the future.
This position demands hands-on problem solving at production scale. You will investigate ambiguous failures spanning networks, databases, cloud infrastructure, and enterprise applications; use AI to formulate hypotheses, validate, and expedite; capture the human logic that trains our systems; and proactively identify patterns that convert isolated fixes into lasting automations. It is not about following scripts, sorting tickets, or "escalating to Level 3." If you excel at lateral thinking when documentation is sparse, if you can transition from packet capture to query plan to workflow trace seamlessly, and if you're confident challenging an LLM when it errs, you will thrive here.
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-TechnicalSuppo.043
We're bridging that divide through an alternative approach: AI-enhanced "cyborg" agents who combine extensive troubleshooting expertise with product knowledge and agentic AI. In this position, you refine, repair, and guide the tools. Each repair strengthens our automation, each root cause investigation becomes a repeatable blueprint, and each edge case you resolve enhances the system for thousands of future customers. This is the intersection of sophisticated troubleshooting, human insight, and AI coordination, delivering quicker resolutions now while building cumulative intelligence for the future.
This position demands hands-on problem solving at production scale. You will investigate ambiguous failures spanning networks, databases, cloud infrastructure, and enterprise applications; use AI to formulate hypotheses, validate, and expedite; capture the human logic that trains our systems; and proactively identify patterns that convert isolated fixes into lasting automations. It is not about following scripts, sorting tickets, or "escalating to Level 3." If you excel at lateral thinking when documentation is sparse, if you can transition from packet capture to query plan to workflow trace seamlessly, and if you're confident challenging an LLM when it errs, you will thrive here.
What You Will Be Doing
- AI-Enhanced Customer Resolutions: Investigate complex tickets escalated by AI systems, deploy human judgment in areas where AI underperforms, and subsequently close the loop by refining the AI system
- Spending two full months onboarding; you will be expected to ramp up on multiple products within the first month (we recognize this is demanding)
- Depending on your managers for assistance; if you are not skilled at unblocking yourself, you will likely find this role challenging
- Combine technical human insight and AI functionality to provide outstanding customer support, concentrating on intricate issues that AI cannot yet completely address
- Must be based 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'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-TechnicalSuppo.043
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