Principal Technical Support Engineer, Trilogy (Remote) – $60,000/Year Usd

At Trilogy, we’ve revolutionized technical support. Our AI systems efficiently resolve routine issues across our portfolio of 100+ enterprise software products. What remains are the challenging, intricate problems that demand exceptional technical expertise and creative thinking—precisely where you come in.

This role is designed for technical support veterans who thrive under pressure, solve problems independently, and adapt rapidly to new technologies. We don’t have time for gradual onboarding or constant guidance—we need someone who can dive into complex technical challenges from day one and deliver results.

If you’re the engineer who colleagues turn to when everyone else is stumped, who learns new systems at remarkable speed, and who sees impossible tickets as intellectual challenges rather than burdens, Trilogy offers you the opportunity to elevate your expertise while solving the problems others can’t.

What You Will Be Doing

• Resolve sophisticated technical issues that our advanced AI systems have escalated, requiring human expertise and creative problem-solving
• Analyze patterns in complex tickets to identify opportunities for expanding AI capabilities
• Collaborate with product teams to close knowledge gaps and enhance our AI-powered support systems
• Master multiple enterprise software products rapidly to provide expert-level technical guidance
• Develop innovative solutions for our most challenging customer issues across diverse technologies

What You Won’t Be Doing

• Handling routine support tickets that our AI systems can resolve
• Taking two months to get up to speed—you’ll be expected to master several products within your first month
• Relying on managers for constant guidance—self-sufficiency is essential for success in this role
• Working within a narrow technical domain—your expertise will span across multiple enterprise products
• Following rigid support playbooks—you’ll need to develop creative solutions for unique challenges

Principal Technical Support Engineer Key Responsibilities

Integrate advanced human technical expertise with AI capabilities to resolve complex customer issues that exceed current AI limitations, while simultaneously improving our AI systems to handle increasingly sophisticated problems.

Basic Requirements

• Minimum 3 years of experience in technical customer support roles with demonstrated expertise in complex problem resolution
• Advanced proficiency with generative AI tools, including creating automated workflows and custom GPTs (basic LLM usage for research or content generation is insufficient)
• Exceptional self-learning capabilities with proven ability to master new technologies rapidly
• Strong analytical thinking and troubleshooting skills across diverse technical domains
• Current residence in North or South America

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-US-RoundRoc-PrincipalTechn.002