Technical Support Engineer at Crossover

The hardest tickets demand more than someone who can follow a script. They require an engineer capable of navigating unclear context, misconfigured systems, conflicting evidence, upset customers, and AI-generated false leads—then determining what the actual problem is. This position is designed for the support engineer who thrives on the unsolved case: replicating the failure, analyzing logs, tracking API behavior, examining JSON payloads, distinguishing a 401 from a 404 from a 429, and leveraging AI aggressively without blind trust.

Traditional support teams still operate on queues, macros, handoffs, and "known issue" documentation. We are doing something different. Routine support is increasingly automated through AI and L1 processes, so human judgment is now reserved for the toughest problems. AI is not replacing you in this role. It is the instrument you direct, validate, challenge, and confirm.

This position is not about copying AI responses, making quick guesses, waiting to be told what to do, or escalating the instant a ticket becomes unfamiliar. It is not suited for someone who masters one product and then stalls when the next issue involves a different stack. It is about delivering the correct answer in the minimum number of customer interactions the issue permits: reproducing before prescribing solutions, investigating across tickets, Slack, knowledge bases, logs, configurations, and concrete evidence before escalating, and composing customer replies clear enough to defuse tension. The technical foundation is required: REST APIs, JSON, HTTP status codes, command line, and logs. That baseline qualifies you. Judgment in ambiguous conditions is what makes you effective.

In this position, your responsibility is to own each issue until it is either resolved or escalated with clarity, including diagnostic logic valuable for the next agent and future AI processes. You will thrive in this role if the ticket that defies explanation is the one you want most. You will dislike it if you need a single product, a single playbook, and someone else to clear obstacles. If that kind of intensity energizes you, please apply.

What You Will Be Doing

• AI-Augmented Customer Resolutions: Resolving ambiguous, escalated tickets by combining in-depth, hands-on troubleshooting with AI that you direct, anchor in actual documentation, and verify.

What You Won’t Be Doing

• Spending two full months ramping up; you will be expected to become proficient on multiple products within the first month (we recognize this is demanding)
• Depending on your managers for assistance; if you are not skilled at unblocking yourself, you will likely find this role challenging

Technical Support Engineer Key Responsibilities

• Combine technical human expertise with AI capabilities to provide exceptional customer support, concentrating on complex issues that AI cannot yet fully address

Basic Requirements

• Must be located in one of the following regions: North America, South America, Australia, New Zealand, Philippines
• At least 2 years of experience in a technical customer support role
• Basic coding skills for the purpose of troubleshooting/bug fixes
• Troubleshooting Skills: Explaining complex issues in simple terms, demonstrating strong problem understanding, recommending relevant troubleshooting strategies, proposing multiple solution paths, and showing attention to detail
• AI Proficiency: A clear understanding of AI tools and their role in support workflows, including knowing their strengths, limitations, and how to use them effectively to solve problems faster

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-Winnipeg-TechnicalSuppo.050