Crossover
Technical Support Engineer, Trilogy (Remote) - $60,000/year USD
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Job Description
Complex tickets require more than rote script execution. They demand someone capable of navigating unclear contexts, misconfigured systems, conflicting evidence, escalated customers, and misleading AI outputs—then determining the actual root cause. This position is designed for the support engineer drawn to the unresolved case: replicating the issue, analyzing logs, following API behavior, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI critically without blind reliance.
Traditional support structures still depend on ticket queues, templated responses, handoff protocols, and documented workaround libraries. We are building something fundamentally different. Straightforward support is increasingly automated through AI and tier-1 processes, leaving human expertise for the hardest technical problems. AI is not a threat to your role here. It is an instrument you command, anchor, interrogate, and validate.
This position does not involve copying AI-generated responses, making hasty assumptions, awaiting direction, or escalating immediately when a ticket becomes unfamiliar. It is not suited for someone who masters a single product and stalls when the next issue involves a different technology stack. It requires delivering the correct answer with the minimum number of customer interactions the problem permits: reproducing before proposing solutions, investigating across tickets, Slack channels, knowledge bases, logs, configurations, and tangible artifacts before escalating, and composing customer communications precise enough to defuse tension. The technical foundation is expected: REST APIs, JSON, HTTP status codes, command-line environments, and log interpretation. That foundation qualifies you. Judgment amid ambiguity is what makes you effective.
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In this position, you own each issue until resolution or clean escalation, providing diagnostic logic valuable for the subsequent agent and the next AI workflow. You will thrive in this role if the ticket that resists explanation is the one you pursue most eagerly. You will struggle if you require a single product, a single playbook, and external assistance to unblock you. If that environment energizes you, we encourage you to apply.
What You Will Be Doing
- AI-Augmented Customer Resolutions: Resolve ambiguous, escalated tickets by pairing thorough, hands-on technical investigation with AI that you direct, anchor to verified documentation, and validate rigorously.
What You Won’t Be Doing
- Spending two full months onboarding; you will be required to ramp up on multiple products within the first month (we acknowledge this pace is demanding)
- Depending on managers for unblocking; if you cannot self-direct and unblock independently, this role will be difficult
Technical Support Engineer Key Responsibilities
- Combine advanced technical human judgment with AI capabilities to provide outstanding customer support, concentrating on intricate issues that AI cannot yet independently resolve
Basic Requirements
- 2+ years in a hands-on technical capacity such as technical support, customer support engineering, software engineering, QA, or sysadmin/DevOps. The job title need not be "support."
- Proficient in making and interpreting REST API calls and JSON, understanding HTTP status codes (such as 401 vs 404 and 429 vs 403), and operating in command-line interfaces (CLI) and logs.
- Practical experience applying generative AI tools (such as ChatGPT or Claude) in your everyday technical workflows.
- Professional-level fluency in written and spoken English.
- Available to work full-time from 1:00 PM – 10:00 PM UTC (8:00 AM – 5:00 PM US Eastern)
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Nice-to-have Requirements
- Background supporting technical or business customers on enterprise software or B2B SaaS, beyond internal IT support.
- API debugging experience with tools like Postman or curl.
- Demonstrated history troubleshooting across multiple unrelated products or technology stacks, not limited to one.
- Developer-level proficiency: capable of reading code or tracing an API call when the situation requires 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 by 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-GB-Leiceste-TechnicalSuppo.004
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