Tier 2 Escalation Specialist (Remote Eligible - Costa Rica)

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day.

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

Get to Know Us:

At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together.

Equal Opportunity Employer:

Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.

#LI-Remote