What are the responsibilities and job description for the Senior Technical Support Engineer, Trilogy (Remote) - $60,000/year USD position at Crossover?
Customer expectations are rising while the support industry struggles with mounting complexity. Today's customers demand AI-driven, immediate solutions, yet most companies remain stuck in pilot phases, unable to convert AI into tangible results. The challenge is about to intensify. Industry projections suggest that by 2029, agentic systems will independently handle the majority of routine issues, creating a widening chasm between what customers expect and what organizations currently deliver.
Our approach bridges this divide through a distinctive framework: AI-enhanced "cyborg" agents who combine sophisticated troubleshooting skills with product expertise and agentic AI capabilities. In this position, you will train, refine, and mentor the tools. Each solution you deliver strengthens our automation infrastructure, every root cause investigation transforms into a reusable framework, and every complex scenario you decode enhances the system for thousands of future customers. This is the intersection where expert troubleshooting, human judgment, and AI coordination converge to produce faster resolutions now while building compounding intelligence for the future.
This position demands hands-on problem resolution at production scale. You will analyze unclear failures spanning networks, databases, cloud infrastructure, and enterprise applications; harness AI to generate hypotheses, validate theories, and accelerate outcomes; capture the human logic that educates our systems; and proactively identify patterns that convert isolated fixes into lasting automations. This is not about following scripts, sorting tickets, or "escalating to Level 3." If you excel at lateral thinking when documentation is sparse, if you can transition seamlessly from packet inspection to execution plans to workflow traces, and if you're prepared to correct an LLM when it errs, this environment will suit you well.
What You Will Be Doing
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-Boston-SeniorTechnica1.009
Our approach bridges this divide through a distinctive framework: AI-enhanced "cyborg" agents who combine sophisticated troubleshooting skills with product expertise and agentic AI capabilities. In this position, you will train, refine, and mentor the tools. Each solution you deliver strengthens our automation infrastructure, every root cause investigation transforms into a reusable framework, and every complex scenario you decode enhances the system for thousands of future customers. This is the intersection where expert troubleshooting, human judgment, and AI coordination converge to produce faster resolutions now while building compounding intelligence for the future.
This position demands hands-on problem resolution at production scale. You will analyze unclear failures spanning networks, databases, cloud infrastructure, and enterprise applications; harness AI to generate hypotheses, validate theories, and accelerate outcomes; capture the human logic that educates our systems; and proactively identify patterns that convert isolated fixes into lasting automations. This is not about following scripts, sorting tickets, or "escalating to Level 3." If you excel at lateral thinking when documentation is sparse, if you can transition seamlessly from packet inspection to execution plans to workflow traces, and if you're prepared to correct an LLM when it errs, this environment will suit you well.
What You Will Be Doing
- AI-Enhanced Customer Resolution: Investigate sophisticated tickets escalated from AI systems, deploy human judgment in domains where AI underperforms, and subsequently enhance the AI infrastructure by addressing identified gaps
- Spending two full months onboarding; you will be required to achieve proficiency across multiple products within the first month (we recognize this timeline is demanding)
- Depending on managers for assistance; if you cannot effectively unblock yourself, this role will present significant challenges
- Combine technical human judgment and AI tools to provide superior customer support, concentrating on sophisticated challenges that AI cannot yet independently resolve
- Must be located in North or South America
- At least 3 total years of experience in a technical customer support role
- Advanced generative AI proficiency (i.e., use of multiple AI tools, ability to automate workflows and custom GPTs); if you've only used LLMs for research, learning, brainstorming, or content generation, that will be deemed insufficient
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-Boston-SeniorTechnica1.009
Salary : $60,000