Technical Support Engineer, Trilogy; Remote

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

Join to apply for the Technical Support Engineer, Trilogy (Remote) - $60,000/year USD role at Crossover
. 1 day ago—be among the first 25 applicants.

Base pay range: $30.00/hr - $30.00/hr (equivalent to $60,000/year).

The support sector is becoming increasingly complex while customers expect AI‑driven, immediate resolutions. Most companies remain in pilot phases, struggling to translate AI into tangible results. By 2029, agentic systems are expected to autonomously handle the majority of routine issues. We are bridging this gap with AI‑enhanced “cyborg” agents that combine extensive troubleshooting expertise with product knowledge and agentic AI. In this position you refine, repair, and guide the tools.

Every repair strengthens automation; every root‑cause investigation becomes a repeatable blueprint; every edge case you resolve enhances the system for thousands of future customers. This role 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, 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.

• AI‑Enhanced Customer Resolutions:
  Investigate complex tickets escalated by AI systems, deploy human judgment where AI under performs, and 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 have 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 three 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.

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-Technical Suppo.
043

• Associate

• Full‑time

• Engineering, Information Technology, and Customer Service

• Software Development, IT Services and IT Consulting, and Telecommunications

We look forward to meeting you!