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

Customer expectations in support are accelerating while industry complexity deepens. Today's customers anticipate instant, AI-driven answers, yet most companies remain stuck in pilot phases, unable to translate AI into tangible results. The challenge is about to intensify. Projections indicate 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 distinct framework: AI-augmented "cyborg" agents who combine sophisticated troubleshooting skills with product expertise and agentic AI capabilities. In this position, you will train, refine, and mentor the tools. Each resolution strengthens our automation layer, every root cause investigation becomes a repeatable playbook, and every outlier you decode enhances the system for thousands of future customers. This is the intersection of advanced technical problem-solving, human judgment, and AI coordination—delivering rapid resolutions now while building cumulative intelligence for the future.

This position demands production-level, hands-on problem solving. You will diagnose unclear failures spanning networks, databases, cloud infrastructure, and enterprise applications; use AI to form hypotheses, run tests, and accelerate outcomes; capture the human logic that trains our systems; and proactively identify trends that transform isolated fixes into lasting automation. This is not script execution, basic ticket sorting, or escalation to "Level 3." If you excel at lateral thinking when documentation is sparse, if transitioning from packet captures to query plans to workflow traces is second nature, and if you're confident challenging an LLM's conclusions, you will thrive here.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Examine escalated tickets beyond AI capability, apply human technical judgment where AI underperforms, and subsequently enhance the AI system to narrow the performance gap
  
  

What You Won’t Be Doing

• Spending two full months onboarding; you will be required to ramp up on multiple products within the first month (we recognize this is an accelerated timeline)
• Depending on managers for unblocking; if self-sufficiency in problem resolution is not your strength, this role will present significant challenges
  
  

Senior Technical Support Analyst Key Responsibilities

• Combine human technical depth and AI tools to provide superior customer support, concentrating on intricate issues that remain beyond full AI resolution
  
  

Basic Requirements

• Must be located in North or South America
• Minimum of 3 years total experience in a technical customer support position
• Advanced proficiency with generative AI (i.e., usage 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 be considered 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 www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-3330-CO-BogotáDC-SeniorTechnica2.005