Customer Support Engineer - Remote

Customer expectations are rising sharply while the support industry struggles with mounting complexity. Today's customers demand AI-driven, instant resolutions, yet most companies remain stuck in pilot mode and fail to deliver meaningful AI outcomes. The challenge is about to intensify. Projections suggest that by 2029, agentic systems will autonomously handle the majority of routine issues, creating a widening chasm between what customers expect and what current support models deliver.
We're bridging that chasm with a fundamentally different approach: AI-augmented "cyborg" agents who combine sophisticated troubleshooting expertise with product knowledge and agentic AI capabilities. In this position, you will train, refine, and guide the tools. Each fix strengthens our automation layer, each root cause investigation becomes a repeatable playbook, and each edge case you resolve enhances the system for thousands of future customers. This is the intersection of advanced troubleshooting, human judgment, and AI orchestration—delivering rapid resolutions now while building compounding intelligence for the future.
This role 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 theories, and accelerate diagnosis; capture the human reasoning that trains our systems; and proactively identify patterns that transform isolated fixes into lasting automations. This is not about following scripts, triaging tickets, or "escalating to Level 3." If you excel at lateral thinking when documentation is sparse, if you can navigate seamlessly from packet analysis to execution plans to workflow traces, and if you're confident challenging an LLM's conclusions, this environment will suit you.
What You Will Be Doing
~ AI-Augmented Customer Resolutions: Investigate complex tickets escalated by AI systems, apply human judgment where AI capabilities fall short, and then enhance the AI system to close those gaps

What You Won’t Be Doing
Spending two full months ramping up; you will be expected to achieve proficiency on multiple products within the first month (we recognize this timeline is aggressive)
Depending on your managers for assistance; if you are not skilled at unblocking yourself, this role will present significant challenges
Technical Support Engineer Key Responsibilities
~ Combine technical human judgment and AI capabilities to provide outstanding customer support, concentrating on complex issues that AI cannot yet fully address

Basic Requirements
Must be based in North or South America
At least 3 total years of experience in a technical customer support role
Basic coding skills for the purpose of troubleshooting/bug fixes (you will be required to take a coding assessment that involves 4 challenges; you will just need to solve the first one!)
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
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 for more details on this topic.
Crossover Job Code: LJ-3330-CA-Winnipeg-TechnicalSuppo.045