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

Remote from: Costa Rica
Annual salary: Undisclosed
Salary information is not provided for this position. Check our Salary Directory to estimate the average compensation for similar roles.
Department: Technical Support
Employment type: Full Time,
Job posted: 5 Jun 2026
Apply before: 5 Jul 2026
Experience level: Midweight
Views / Applies: 11 / 3

About company

About Smartsheet

Smartsheet is a platform for work management and automation solutions.

Computer Software
2005

Actively Hiring

AI Summary

Smartsheet is hiring a Technical Support Specialist II for Governance and Ops, based remotely in Costa Rica. The role involves troubleshooting customer issues via email, phone, and chat, contributing to team projects, and achieving product certification. Candidates need 1+ years of experience and excellent communication skills. The position offers benefits like paid leave, health insurance, and professional development opportunities. It's a collaborative role with moderate autonomy and a standard support pace.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight This role requires 1+ years of experience and involves troubleshooting customer issues, but the technical depth is moderate, making it a manageable challenge for early-career professionals.

Salary Analysis

AI Insight The offered salary is not specified, but based on US market data, a Technical Support Specialist II typically earns between $45,000 and $70,000 annually. Given the remote location in Costa Rica, the actual compensation may be adjusted for local market rates.

Key Skills

Technical Support Customer Service Troubleshooting Communication Problem Solving Collaboration SaaS CRM Product Knowledge Remote Support

Cover Letter Sample

Dear Hiring Manager,

I am writing to express my enthusiasm for the Technical Support Specialist II position at Smartsheet. With over a year of experience in technical support and a passion for solving problems, I am confident in my ability to deliver outstanding service to your customers. My strong communication skills and ability to empathize with users make me an ideal fit for this role.

In my previous role, I successfully resolved complex technical issues while maintaining high customer satisfaction scores. I am eager to become Smartsheet Product Certified and contribute to your team's success. I thrive in collaborative environments and am committed to continuous improvement.

Thank you for considering my application. I look forward to the opportunity to discuss how I can add value to Smartsheet.

Sincerely,
Your Name

Possible Interview Questions

How do you prioritize multiple support tickets with varying levels of urgency?

I categorize tickets by impact and urgency, using a triage system to address critical issues first. I also communicate with customers about expected timelines and escalate when necessary.

Describe a time you had to explain a technical concept to a non-technical customer.

Once, a customer was confused about a software integration. I used analogies and step-by-step screenshots to simplify the process, ensuring they understood without technical jargon.

How do you stay updated on product changes and new features?

I regularly review release notes, participate in training sessions, and use internal knowledge bases. I also set up alerts for updates to ensure I'm always informed.

Can you give an example of a difficult customer interaction and how you resolved it?

A frustrated customer had a recurring issue that seemed unresolved. I listened actively, apologized for the inconvenience, and escalated to a senior team while keeping the customer updated. The issue was fixed, and they appreciated the transparency.

What does excellent customer service mean to you?

It means being empathetic, responsive, and taking ownership of the problem. It's not just about fixing the issue but also ensuring the customer feels valued and heard throughout the process.

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.

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