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Senior Technical Support Engineer, Trilogy (Remote) - $60,000/year USD

TrilogyRemoteMay 23rd, 2026
Forget everything you know about traditional technical support. At Trilogy, we're revolutionizing the industry with cutting-edge AI integration across our suite of 100+ enterprise software products. While our AI handles the routine, you'll be tackling the exceptional – the puzzles that make even artificial intelligence scratch its head.This isn't your average support role where you'll spend days explaining how to reset passwords. We've eliminated the mundane, leaving only the most intellectually stimulating challenges for our human experts. Think of yourself as a technical detective, solving complex mysteries that require both human intuition and technical prowess.Fair warning: this role demands immediate impact. We're looking for self-starters who thrive in deep water and can navigate complex technical landscapes without a GPS. If you need constant direction or prefer a gentle learning curve, this isn't your arena.But if you're energized by challenging problems and want to be at the forefront of AI-human collaboration in technical support, you've found your calling. This role offers unprecedented exposure to diverse technical challenges and the opportunity to shape the future of customer support technology.What You Will Be DoingYou'll be the bridge between AI and human expertise, handling the most sophisticated technical challenges that emerge from our AI-first support system. Your role involves dissecting complex issues, implementing innovative solutions, and continuously enhancing our AI capabilities based on your insights and resolutions.Don't ExpectWhat you won’t be doingA leisurely onboarding period - you'll need to master multiple products within your first monthHand-holding from management - self-sufficiency isn't just preferred, it's essentialSenior Technical Support Engineer Key ResponsibilitiesYour core mission is to seamlessly blend human technical expertise with our advanced AI systems, focusing on:Resolving sophisticated technical challenges that exceed current AI capabilitiesContributing to the continuous evolution of our AI support systemsDelivering high-caliber solutions that maintain our reputation for technical excellenceBasic Requirements3+ years of hands-on technical support experience in complex software environmentsDemonstrated mastery of generative AI tools, including experience with workflow automation and custom GPT development (basic AI usage for content creation or research isn't sufficient)Exceptional problem-solving abilities and self-directed learning capabilitiesAbout TrilogyHundreds 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 usThis 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-US-COUNTRY-SeniorTechnica1.002