Technical Support Engineer

Role Overview

This position is for a support engineer who enjoys untangling difficult problems rather than following a script. The work involves investigating unclear incidents, checking misconfigured systems, weighing conflicting clues, handling frustrated customers, and spotting misleading AI-generated suggestions before identifying the real root cause.

The role is built around complex support cases where routine inquiries are increasingly handled by automation and first-line processes. Here, human expertise is focused on the hardest issues, and AI is used as a tool to be directed, checked, challenged, and verified—not blindly trusted.

You will be expected to solve problems with minimal back-and-forth by reproducing failures, comparing tickets and Slack discussions, reviewing documentation and logs, inspecting configurations, and drafting customer updates that reduce confusion and tension. Strong fundamentals in REST APIs, JSON, HTTP status codes, command line tools, and log analysis are essential. Good judgment in uncertain situations is what separates success from failure in this role.

What You Will Do

• Handle ambiguous, escalated customer issues by combining hands-on troubleshooting with AI-assisted workflows, while confirming every AI output against evidence and documentation.
• Investigate failures by reproducing the issue, reviewing logs and configurations, tracing API behavior, and determining the true source of the problem.
• Prepare clear customer-facing responses that explain the situation and help calm escalations.
• Own each case through to resolution or a thorough handoff that gives the next engineer enough diagnostic detail to continue efficiently.
• Use AI as an assistive tool for analysis and productivity, while maintaining a skeptical, evidence-based approach.

What This Role Is Not

• You should not expect a long onboarding period; effectiveness across multiple products is expected within the first month.
• This is not a role for someone who needs frequent managerial help to move forward on technical problems.
• It is not suited to candidates who rely on a single product specialty and struggle when the next case involves a different technology stack.
• You will not be copying AI-written answers or making guesses without verification.

Requirements

• At least 2 years of experience in a hands-on technical role such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps; the job title itself does not need to be support.
• Strong working knowledge of REST APIs, JSON, HTTP status codes including the differences between 401, 404, 429, and 403, plus comfort using CLI tools and reading logs.
• Regular real-world use of generative AI tools such as ChatGPT or Claude in technical work.
• Professional fluency in English, both spoken and written.
• Ability to work a full 40-hour week during US business hours in Eastern Time, including overnight coverage depending on your time zone.
• Residence in North America, Central America, South America, Australia, New Zealand, the United Kingdom, Ireland, or the Philippines, as relocation support is not offered.
• Experience supporting technical or business users on enterprise software or B2B SaaS is preferred.
• API debugging experience with tools such as Postman or curl is preferred.
• Comfort troubleshooting across multiple unrelated products or technology stacks is preferred.
• Developer-level ability to read code or follow an API request path when needed is preferred.

About the Company

Trilogy operates hundreds of software businesses through its platform. Over the past three decades, the company has emphasized finding exceptional talent, building new technology, and incubating new ventures. Its product approach focuses on simple customer-facing design, modern cloud-based architecture, and continuous innovation.

Working Arrangement

This is a full-time, long-term independent contractor role arranged through Crossover as the Contractor of Record. The role is available immediately and follows a 40-hour workweek.

Compensation

The pay rate is USD 30 per hour, which works out to approximately USD 60,000 per year based on 40 hours per week and 50 weeks per year. Payment is made weekly.

Additional Information

Crossover job code: LJ-3330-IE-COUNTRY-TechnicalSuppo.001