Overview
Technical Support Engineer, Trilogy (Remote) – $60,000/year USD Jobs in Nairobi, Nairobi County, Kenya at Crossover
Title: Technical Support Engineer, Trilogy (Remote) – $60,000/year USD
Company: Crossover
Location: Nairobi, Nairobi County, Kenya
The difficult tickets are not looking for someone who simply follows a script. They require a person who can step into unclear situations, misconfigured systems, conflicting evidence, unhappy customers, and AI outputs that lead nowhere—then determine what the actual problem is. This role is designed for the support engineer who enjoys the unresolved case: replicating the error, analyzing logs, tracking API activity, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI effectively without blind reliance.
Most support organizations remain structured around ticket queues, templated responses, handoff processes, and documented workaround libraries. We are constructing something different. Routine inquiries are increasingly managed by AI and L1 processes, which means human expertise is allocated to the toughest challenges. AI is not replacing you in this role. It is the instrument you control, validate, question, and confirm.
This position is not about copying AI-generated answers, making rapid guesses, awaiting direction, or escalating as soon as the issue becomes unfamiliar. It is not suited for someone who specializes deeply in one product and hesitates when the next ticket involves a different technology stack. It is about delivering the correct answer with the minimum number of interactions the problem permits: reproducing issues before proposing solutions, investigating across tickets, Slack threads, knowledge bases, logs, configurations, and actual evidence before escalating, and composing customer replies that are clear enough to defuse tension. The technical foundation is assumed: REST APIs, JSON, HTTP status codes, command line, and logs. That qualifies you for consideration. Sound judgment in ambiguous conditions is what makes you effective.
In this position, you are accountable for the issue until it is either solved or escalated with clarity, accompanied by diagnostic reasoning valuable to the next engineer and the next AI workflow. You will find this role rewarding if the ticket that resists explanation is the one you prefer. You will dislike it if you require a single product, a single playbook, and external assistance to proceed. If that kind of challenge focuses you, we encourage you to apply.
What You Will Be Doing
- AI-Augmented Customer Resolutions: Resolving ambiguous, escalated tickets by blending thorough, hands-on diagnostic work with AI that you steer, anchor in verified documentation, and cross-check.
What You Won’t Be Doing
- Spending two full months onboarding; you will be expected to ramp up on several products within the first month (we recognize this is demanding)
- Depending on your managers to remove obstacles; if you are not skilled at self-unblocking, you will likely find this role difficult
Technical Support Engineer Key Responsibilities
- Integrate technical human expertise and AI capabilities to deliver exceptional customer support, focusing on complex issues that AI cannot yet fully resolve
Basic Requirements
- 2+ years in a hands-on technical role such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The title does not need to be "support."
- Comfortable making and reading REST API calls and JSON, interpreting HTTP status codes (such as 401 vs 404 and 429 vs 403), and working in a command line (CLI) and logs.
- Hands-on experience using generative AI tools (such as ChatGPT or Claude) in your daily technical work.
- Professional fluency in English, written and spoken.
- Able to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)
Nice-to-have Requirements
- Experience supporting technical or business customers on enterprise software or B2B SaaS, not just internal IT.
- API troubleshooting with tools like Postman or curl.
- A track record of troubleshooting across several unrelated products or tech stacks, not just one.
- Developer-grade depth: you can read code or trace an API call when the problem demands it.
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 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 in leaps and bounds.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
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 www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-3330-KE-Nairobi-TechnicalSuppo.147