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Technical Support Specialist II - Governance and Ops (Remote Eligible - Costa Rica)

July 9, 2026

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. Energized by solving problems and providing outstanding support? There's never been a better time to join Smartsheet! As a Technical Support Specialist, you will report to one of our Support Team Managers and work with team members across the globe. Your responsibilities will include delivering support to our customers, maintaining high service standards, and contributing to team projects. 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 Manager. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica. You Will: - Troubleshoot customer issues using internal & external documentation, various tools, and other resources such as escalation resources to resolve customer issues and deliver great customer experiences - Become Smartsheet Product Certified and work with customers through a variety of channels including email, phone, and chat - Partner with leaders to meet or exceed performance goals in areas like customer satisfaction, quality assurance, and attendance - Become an expert in a specific product area - Contribute to team projects - Give and receive thoughtful feedback on team processes and leadership - Manage other responsibilities as assigned You Have: - Excellent written, verbal and interpersonal communication skills - 1+ years of 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 - Working knowledge of assigned feature a plus - Flexibility in your working hours as this position will require work outside of standard business hours Perks & Benefits: - Fully paid Health & Life insurance for full-time employees and family members - Monthly stipend to support your work and productivity - 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 LinkedIn Learning 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. #LI-Remote

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...