Technical Support Engineer, Trilogy; Remote

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

Join as a Technical Support Engineer for Trilogy’s AI‑augmented cyber‑bot customer support platform. Your role will involve troubleshooting complex technical issues, refining AI workflows, and building automated solutions for production‑scale incidents.

$30.00/hr – $30.00/hr (≈ $60,000/year)

Customers expect AI‑driven instant responses, yet most organizations struggle to turn AI into tangible results. This role bridges that gap by teaching, refining, and mentoring AI tools, turning each ticket resolution into cumulative intelligence that benefits thousands of future customers.

• AI‑Augmented Customer Resolutions:
  Examine complex tickets escalated by AI systems, apply human judgment where AI under performs, and enhance the AI system to close the gap.

• Spending two full months onboarding; you will be expected to achieve product proficiency within the first month.
• Relying on managers for assistance; you must unblock yourself effectively.

• Combine technical human judgment and AI capabilities to handle intricate customer issues that AI cannot resolve independently.

• Must be located in North or South America.
• Minimum of 3 years total experience in a technical customer support role.
• Advanced generative AI proficiency (using multiple AI tools, automating workflows, creating custom GPTs). LLM use only for research or content generation is insufficient.

Hundreds of software businesses run on the Trilogy Business Platform. Trilogy has thrived for three decades on talent acquisition, technological innovation, and business incubation. Our culture focuses on simple customer‑facing designs, moon‑shot ideas, and modern cloud‑based stack re‑architecting.

This is a full‑time, 40‑hour per week, long‑term position. It requires entering into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $30 USD/hour (≈ $60,000/year). The payment period is weekly. For more information visit

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We look forward to meeting you!