Technical Support Engineer - Remote (Nairobi)

About the Role

This role is ideal for a support engineer who thrives on resolving challenging, unclear issues rather than following scripted responses. You'll handle complex tickets involving misconfigured systems, conflicting evidence, unhappy customers, and AI outputs that are not straightforward. Your task will be to accurately diagnose problems by replicating errors, analyzing logs and API activities, interpreting JSON payloads, and differentiating HTTP status codes such as 401, 404, and 429. Effective use of AI as a tool—rather than a crutch—is central to your success.

Unlike many support teams that rely heavily on templated responses and ticket queues, this position focuses on leveraging human expertise for the toughest technical challenges. Basic inquiries are mostly managed through AI and first-level support, leaving you to work on the most complex problems that require thorough investigation and sound judgment in ambiguous conditions.

You are expected to reproduce problems before recommending solutions, perform detailed investigations using various resources including Slack threads, knowledge bases, logs, configurations, and documented evidence, and write clear communications to de-escalate customer frustrations. The role requires a solid foundation in REST APIs, JSON, HTTP protocols, command line interfaces, and log interpretation.

Responsibilities

• Employ AI-augmented methods to resolve ambiguous and escalated customer issues by combining hands-on diagnostics with verified documentation and thorough validation.
• Own support tickets fully until solutions are provided or escalate them with comprehensive diagnostic reasoning to assist other engineers and AI processes.
• Rapidly onboard and become proficient with multiple products within the first month, managing self-unblocking without heavy reliance on management support.

Qualifications

• Minimum 2 years of practical experience in technical roles such as technical support, customer support engineering, software engineering, QA, or DevOps; formal job title is flexible.
• Proficient in making and interpreting REST API calls and JSON data, distinguishing between various HTTP status codes (e.g., 401 vs 404 vs 429), and navigating command-line interfaces and logs.
• Experience integrating generative AI tools like ChatGPT or Claude in daily technical workflows.
• Fluent in both written and spoken English.
• Availability to work full-time aligned with 1:00 PM to 10:00 PM UTC (8:00 AM to 5:00 PM US Eastern Time).

Preferred Skills

• Experience providing technical or business customer support in enterprise software or B2B SaaS environments.
• Familiarity with API troubleshooting tools such as Postman or curl.
• Demonstrated ability to troubleshoot across different, unrelated products or technology stacks.
• Developer-level skills in reading code and tracing API requests as needed.

About Trilogy

Trilogy powers hundreds of software companies through its Business Platform, with a history spanning three decades of exceptional talent recruitment, technological innovation, and business incubation. The company emphasizes simple, user-focused technological designs and evolves projects within modern cloud architectures, offering a collaborative environment for professional growth.

Employment Details

This opportunity is a full-time, long-term independent contractor role with Crossover. You'll be compensated $30 per hour, amounting to an annual salary estimate of $60,000 based on 40 hours per week over 50 weeks. Payments are disbursed weekly. The contract type is that of Contractor of Record.