Tier 2 Escalation Specialist (Remote Eligible - Costa Rica)

Smartsheet · San Jose, CR · Other

Posted 2026-11-13

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Smartsheet is looking for a Support Specialist who will be responsible for tackling complex technical issues. You will troubleshoot, test, and document complicated and often unique technical issues. This position requires a highly motivated individual who can collaborate in an environment that fosters knowledge sharing and rapid problem-solving in order to resolve customer technical issues efficiently.

At Smartsheet Support we empathize and empower others with expert engagements and are the first line of response for our customers to fix issues, share best practices, and advocate for users. Our teams of experts are aligned to various domains of knowledge, promoting the most effective and expedient customer resolution.

You will report to a Support Pod Manager. This role is eligible for remote work within Costa Rica. You  must reside in Costa Rica.

You Will:

Handle customer technical issues with a high sense of urgency and ownership while keeping stakeholders appropriately apprised of the investigation

Troubleshoot issues using internal & external documentation, analyze log files, use various tools and other resources to identify root causes and resolve customer issues

Contribute to your team’s goals by thoroughly researching, testing, and documenting your investigations as you collaborate with colleagues to help them progress their cases as well as your own

Share your expertise, provide guidance on troubleshooting techniques, and help upskill your colleagues

Work with customers through a variety of channels including email, phone, and chat

Work closely & collaboratively with colleagues on a daily basis to help research and resolve the most complex customer impacting issues

Contribute to internal & external documentation

Manage other responsibilities as assigned

You Have:

2+ years technical or customer support experience, or equivalent

Ability to demonstrate empathetic and confident issue ownership, assuring customers that if you can't solve their problem, you will ensure they are directed to the right resource

Confidence and strong interest in problem solving

Excellent written, verbal, and interpersonal communication skills

Ability to work independently or collaboratively in a fast-paced environment

Working knowledge of assigned feature strongly preferred

A firm grasp of and comfort using cloud applications

Desire and aptitude to quickly ramp up on new technologies, languages, and frameworks

Conceptual understanding of a RESTful service

Willingness to engage on complex matters

Comfortable working in ambiguous situations with little to no direction

Flexibility in your working hours as this position will require work outside of standard business hours

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