Technical Support Engineer

Role Overview

This role is built for a support professional who enjoys digging into difficult technical cases rather than following a script. You’ll be expected to investigate vague issues, broken configurations, inconsistent evidence, difficult customers, and even inaccurate AI suggestions before identifying the real cause.

The work focuses on complex support problems where human judgment still matters most. Routine issues are increasingly automated, so this position concentrates on the hardest technical cases. AI is part of the toolkit here, but it must be guided, challenged, and confirmed by you rather than trusted blindly.

You will not be copying AI-written replies, waiting for instructions, or escalating every unfamiliar issue immediately. Instead, you should be able to reproduce problems, inspect logs and API behavior, review JSON payloads, compare HTTP responses, and communicate clearly and calmly with customers. The role expects a strong technical base plus the ability to make good decisions when the situation is unclear.

You will own each ticket through resolution or through a well-documented escalation path, so the next support agent or automated workflow has useful diagnostic context. This job is a strong fit for someone who gets energized by the hardest unresolved cases and is comfortable working independently across different technologies.

What You Will Do

• Use AI as a support tool while independently investigating and resolving ambiguous technical tickets.
• Reproduce issues, analyze logs, inspect API behavior, and review JSON or other technical artifacts to find root causes.
• Handle escalated customer problems with precise, effective communication.
• Build clear diagnostic notes and handoff details when a ticket truly needs escalation.
• Work across multiple products and systems rather than relying on a single familiar playbook.

What the Role Expects

• Ramp up quickly across several products within the first month.
• Work independently without relying on managers to unblock every step.
• Provide the correct answer with as few customer interactions as the issue allows.

Responsibilities

• Resolve complex, escalated support cases by combining hands-on technical troubleshooting with carefully validated AI assistance.
• Investigate issues by reproducing problems, checking logs, tracing API calls, and reviewing configurations and artifacts.
• Differentiate technical signals such as HTTP 401, 404, 429, and 403 responses, and use that understanding to isolate the source of the problem.
• Use command-line tools and other debugging methods to verify system behavior.
• Write customer responses that are clear, accurate, and calming in tense situations.
• Own tickets until they are solved or cleanly escalated with enough detail for the next handler.

Requirements

• At least 2 years of practical experience in a hands-on technical role such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps.
• Strong working knowledge of REST APIs and JSON, including the ability to make and interpret API calls.
• Comfort with HTTP status codes and what they mean in troubleshooting scenarios.
• Experience working in command-line interfaces and reviewing logs.
• Regular use of generative AI tools such as ChatGPT or Claude in technical workflows.
• Excellent written and spoken English.
• Availability to work full time from 1:00 PM to 10:00 PM UTC, which is 8:00 AM to 5:00 PM US Eastern.
• Ability to work as an independent contractor under a Contractor of Record agreement.

Nice-to-Have

• Experience supporting enterprise software or B2B SaaS customers rather than only internal IT users.
• Hands-on API debugging experience with tools such as Postman or curl.
• Proven ability to troubleshoot across multiple products or unrelated technology stacks.
• Developer-level technical comfort, including reading code or tracing an API request when needed.

About the Company

Trilogy supports hundreds of software businesses through its business platform. Over the past three decades, the company has focused on hiring strong talent, building new technology, and creating new businesses. Its work includes both fresh product ideas and modernizing existing systems onto cloud-based architecture.

Working Arrangement

This is a full-time role with a 40-hour workweek and is intended to be long term. The position is available immediately. Employment is through an independent contractor agreement with Crossover acting as the Contractor of Record.

Compensation

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

Additional Information

Crossover Job Code: LJ-3330-KE-Nairobi-TechnicalSuppo.146