Principal Technical Support Engineer $60,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
Customer expectations in support are rising sharply while organizational complexity continues to deepen. Today's customers anticipate immediate, AI-driven resolutions, yet most companies remain stuck in pilot phases and fail to translate AI into measurable results. The bar is about to rise even further. Agentic systems are expected to autonomously handle the majority of routine issues by 2029, creating a widening chasm between what customers demand and what most support teams can deliver.
We are bridging that divide through a fundamentally different approach: AI-augmented "cyborg" agents who combine advanced troubleshooting expertise with product knowledge and agentic AI capabilities. In this position, you will train, refine, and mentor the tools themselves. Each problem you resolve strengthens our automation frameworks, every root cause investigation becomes a repeatable procedure, and every edge case you decode enhances the system for thousands of future customers. This is the intersection of sophisticated troubleshooting, human judgment, and AI orchestration—delivering rapid resolutions now while building compounding intelligence for the future.
This position demands hands-on problem solving at production scale. You will diagnose ambiguous failures spanning networks, databases, cloud infrastructure, and enterprise applications; use AI to generate hypotheses, execute tests, and accelerate resolutions; capture the human reasoning that trains our systems; and proactively identify patterns that transform 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 transition seamlessly from packet captures to query plans to workflow traces, and if you are confident correcting an LLM when it errs, you will thrive here.
What you will be doing
- AI-Augmented Customer Resolutions: Investigate complex tickets escalated by AI systems, apply specialized human judgment where AI is insufficient, and subsequently enhance the AI system to close those gaps
What you will NOT be doing
- Spending two full months onboarding; you will be expected to achieve proficiency across multiple products within the first month (we recognize this is demanding)
- Depending on your managers for assistance; if you lack the ability to unblock yourself independently, this role will present significant challenges
Key responsibilities
- Combine technical human judgment and AI capabilities to provide outstanding customer support, concentrating on sophisticated issues that AI cannot yet independently resolve
Candidate requirements
- 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
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
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