Content Designer II at Smartsheet - Remote Costa Rica — Columbus
Traveler-Friendly Insight
This role is remote within Costa Rica only — you must be a registered resident or have legal authorization to work in Costa Rica. It is not a "work from anywhere" position, so globe-trotting nomads will need to be based in-country to qualify.
Timezone considerations: Costa Rica operates on CST (UTC-6) year-round with no daylight saving time. This aligns well with US Central and Eastern teams, making synchronous collaboration with Smartsheet's North American headquarters very feasible. Async-friendly elements like content design work (audits, documentation, frameworks) suggest some schedule flexibility, though cross-functional collaboration with Product and Engineering will likely require overlap hours.
For nomads already in Costa Rica, this is an excellent opportunity. Popular bases like San José, Santa Teresa, or Tamarindo offer coworking spaces, stable internet, and a growing digital nomad community. Costa Rica's digital nomad visa (valid up to 2 years) is a practical path for foreign nationals wanting to stay legally while working remotely.
Cost of living context: Without a published salary, it's hard to benchmark precisely, but Costa Rica's cost of living is moderate — San José runs roughly $1,500–$2,200/month for a comfortable lifestyle, significantly lower than equivalent US markets. The monthly productivity stipend and fully covered health insurance add meaningful real-world value on top of base pay.
- Coworking: No explicit coworking allowance mentioned, but the monthly stipend may cover it.
- Equipment: Not specified — worth asking during interview.
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.
As a Content Designer II at Smartsheet, you'll collaborate with cross-functional teams to ensure UX content delivers high value and meets business goals. In this era of rapid innovation, you will play a pivotal role in shaping how our users interact with AI-driven features, ensuring that complex technology feels intuitive, ethical, and human-centric. You'll impact specific feature areas and contribute to platform-wide strategies that define the future of collaborative work management.
You will report to our Director, Content & Globalization. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica.
What you'll do
- Design for AI & LLMs: Partner with Product and Engineering to design conversational interfaces, prompt-based interactions, and AI-generated outputs. You will ensure AI responses are accurate, helpful, and maintain Smartsheet's brand voice.
- Collaborative Creation: Understand user needs and business goals to co-create product content alongside design and product management teams.
- Strategic Content Design: Apply and evolve content strategies, guidelines, and processes. Create deliverables such as content audits, research-driven frameworks, and user personas.
- Information Architecture: Design clear navigation and content hierarchies that help users manage complex data and workflows efficiently.
- Advocacy & Education: Educate cross-functional partners on Content Design best practices and the ethical implications of AI communication.
- Continuous Learning: Stay current on emerging trends in UX, Human-Centered Design, and Generative AI to keep our platform at the cutting edge of the industry.
What you'll bring
- Experience: 3+ years in Content Strategy, Content Design, or UX Writing within a software development organization.
- AI Literacy: Experience (or a deep, demonstrated interest) in designing for AI/ML features. This includes understanding prompt engineering, model personality, and the nuances of human-AI interaction.
- Tool Proficiency: Expertise in Figma and experience working within a robust design system.
- Systems Thinking: Ability to create content that scales globally and translates well across different languages and cultures.
- User-Centric Mindset: A passion for human-centered design and a track record of using research to inform content decisions.
- Communication: Excellent collaboration skills and the ability to champion the "why" behind content decisions to stakeholders.
- Education: Bachelor's degree in a related field.
- Support other duties as assigned.
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, 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.
Frequently Asked Questions
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