Application Support Engineer, Trilogy (Remote) - $60,000/year USD at Crossover
Date: 13 hours ago
City: Ottawa, ON
Contract type: Full time
Remote
Customer expectations in support are rising while the industry struggles with mounting complexity. Today's customers anticipate instant, AI-driven resolutions, yet most companies remain stuck in pilot phases, unable to convert AI into tangible results. The challenge is about to intensify. Industry forecasts suggest 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.
Our approach bridges this divide through a hybrid model: AI-enhanced "cyborg" support agents who combine sophisticated troubleshooting skills with product mastery and agentic AI capabilities. In this position, you refine, repair, and mentor the tools themselves. Each resolution strengthens our automation layer, every root cause investigation becomes a repeatable framework, and every anomaly you solve enhances the system for thousands of future customers. This is the intersection of expert troubleshooting, human judgment, and AI coordination—delivering rapid resolutions now while building cumulative intelligence for the future.
This position centers on hands-on problem resolution at production scale. You will investigate vague failures spanning networks, databases, cloud infrastructure, and enterprise applications; harness AI to generate hypotheses, validate theories, and accelerate diagnosis; capture the human logic that trains our systems; and proactively identify patterns that transform isolated fixes into lasting automations. This 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 seamlessly from packet analysis to execution plans to workflow traces, and if you're confident challenging an LLM's conclusions, this role will suit you.
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-Ottawa-ApplicationSup.019
Our approach bridges this divide through a hybrid model: AI-enhanced "cyborg" support agents who combine sophisticated troubleshooting skills with product mastery and agentic AI capabilities. In this position, you refine, repair, and mentor the tools themselves. Each resolution strengthens our automation layer, every root cause investigation becomes a repeatable framework, and every anomaly you solve enhances the system for thousands of future customers. This is the intersection of expert troubleshooting, human judgment, and AI coordination—delivering rapid resolutions now while building cumulative intelligence for the future.
This position centers on hands-on problem resolution at production scale. You will investigate vague failures spanning networks, databases, cloud infrastructure, and enterprise applications; harness AI to generate hypotheses, validate theories, and accelerate diagnosis; capture the human logic that trains our systems; and proactively identify patterns that transform isolated fixes into lasting automations. This 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 seamlessly from packet analysis to execution plans to workflow traces, and if you're confident challenging an LLM's conclusions, this role will suit you.
What You Will Be Doing
- AI-Enhanced Customer Problem Solving: Investigate escalated complex tickets that AI systems cannot fully resolve, apply human judgment where AI capabilities fall short, then enhance the AI system to narrow that gap
- Spending two full months onboarding; you will need to achieve proficiency across multiple products within the first month (we acknowledge this timeline is ambitious)
- Depending on managers for unblocking; if you cannot effectively remove your own obstacles, this role will present significant challenges
- Combine technical human judgment and AI tools to provide outstanding customer support, concentrating on sophisticated issues that AI systems cannot yet independently handle
- Must be located in North or South America
- Minimum of 3 years total experience in technical customer support positions
- Advanced proficiency with generative AI tools (including 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 requirement
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-Ottawa-ApplicationSup.019
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