Tier 2 Escalation Specialist

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday.

Smartsheet is looking for a Support Specialist who will be responsible for tackling complex technical issues. . Successful individuals in this role will enjoy troubleshooting, testing, and documenting 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.

In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to achieve their very best work. Today, we provide a cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better results.

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

• Other job duties 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

Teleworking options from any registered location in Costa Rica (role specific)

Perks & Benefits:

• Fully paid Health & Life insurance for full-time employees and family members

• Monthly stipend to support your work and productivity

• Asociacion Solidarista with employee and employer contributions as well as potential alliances with entities such as universities, gyms, etc.

• 12 days paid Vacation + Flexible Time Away Program

• 20 weeks fully paid Maternity Leave

• 12 weeks fully paid Paternity/Adoption Leave

• Personal paid Volunteer Day to support our community

• Opportunities for professional growth and development including access to Udemy online courses

• Company Funded Perks including a counseling membership and your own personal Smartsheet account

• Teleworking options from any registered location in Costa Rica (role specific)

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, and India. 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.

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