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

Most support engineers waste their careers on repetitive, mundane tickets that could be handled by a chatbot. You're not most engineers.

At Trilogy, we've eliminated the noise. Our AI handles 90% of customer issues across 100+ enterprise software products, leaving only the most complex, intellectually challenging problems for our elite technical team. Every ticket you touch requires deep thinking, creative problem-solving, and genuine expertise.

This isn't a role for those who need hand-holding or prefer predictable routines. We're looking for exceptional engineers who thrive on complexity, learn at lightning speed, and can operate independently from day one. If you're ready to work exclusively on problems that matter—and accelerate your technical growth beyond what any traditional support role could offer—this is your opportunity to join the top 1%.

What You Will Be Doing

• Resolve the most complex technical issues that our AI systems escalate, requiring deep product knowledge and creative problem-solving approaches
• Analyze patterns in AI-escalated tickets to identify gaps in our automation, then collaborate with AI teams to enhance system capabilities
• Serve as the technical bridge between customer needs and product teams, translating complex issues into actionable insights
• Master multiple enterprise software products rapidly, becoming a subject matter expert across Trilogy's diverse portfolio
  
  

What You Won’t Be Doing

• Handling routine password resets, basic configuration questions, or other issues that AI can resolve
• Spending months in training programs—you'll be expected to contribute meaningfully within weeks
• Waiting for detailed documentation or step-by-step guidance—you'll need to figure things out independently
• Working on the same types of problems repeatedly—every challenge will push your technical boundaries
  
  

Senior Technical Support Engineer Key Responsibilities

Drive exceptional customer outcomes by applying advanced technical expertise to solve the most complex support challenges that define Trilogy's reputation for excellence.

Basic Requirements

• Minimum 3 years of technical customer support experience with demonstrable expertise in complex problem resolution
• Advanced AI proficiency including workflow automation, custom GPT development, and integration of multiple AI tools in professional workflows
• Proven ability to learn new technical systems rapidly and operate independently with minimal guidance
• Located in North or South America for optimal collaboration with distributed teams
  
  

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-CA-Calgary-SeniorTechnica1.002