[All remote jobs](https://jobicy.com/jobs.md)[![Smartsheet logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/8b6103bd-221.jpg)](https://jobicy.com/company/smartsheet.md)[Smartsheet](https://jobicy.com/company/smartsheet.md) # Content Designer II (Remote Eligible – Costa Rica) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/smartsheet.md)ShareRemote from[Costa Rica](https://jobicy.com/job-region/costa-rica.md)SalaryUndisclosedDepartment[Web, UI & UX Design](https://jobicy.com/categories/web-app-design.md)EmploymentFull TimeExperienceDirectorPublished23 Oct 2026Apply before22 Nov 2026Listing views53Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Smartsheet is seeking a mid-level Content Designer to shape UX content for collaborative work-management software, including AI-driven product experiences. The role partners closely with product, engineering, and design teams to create conversational interfaces, prompt-based interactions, information architecture, and scalable content standards. The successful candidate will use research and systems thinking to make complex workflows and AI capabilities clear, ethical, and human-centered. This is a remote, full-time role restricted to candidates residing in Costa Rica, with an emphasis on Figma, design systems, localization readiness, and stakeholder advocacy. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe position requires strong UX-writing fundamentals plus the emerging specialization of designing trustworthy AI and LLM interactions. Success depends on independently applying content strategy while aligning many cross-functional stakeholders around clear content decisions. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$55,000US market range (per year)$45k–$65k0$71.50k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer salary was disclosed. The yearly cadence and USD market estimate are inferred for a mid-level, full-time remote Content Designer role in Costa Rica; actual compensation may vary by local payroll structure, experience, and benefits. ## Core skills Skills and capabilities most closely associated with this opportunity. [UX writing](https://jobicy.com/jobs?search_keywords=UX%20writing.md)[Content strategy](https://jobicy.com/jobs?search_keywords=Content%20strategy.md)[Content design](https://jobicy.com/jobs?search_keywords=Content%20design.md)[AI content design](https://jobicy.com/jobs?search_keywords=AI%20content%20design.md)[Prompt engineering](https://jobicy.com/jobs?search_keywords=Prompt%20engineering.md)[Conversational UX](https://jobicy.com/jobs?search_keywords=Conversational%20UX.md)[Information architecture](https://jobicy.com/jobs?search_keywords=Information%20architecture.md)[Figma](https://jobicy.com/jobs?search_keywords=Figma.md)[Design systems](https://jobicy.com/jobs?search_keywords=Design%20systems.md)[User research](https://jobicy.com/jobs?search_keywords=User%20research.md)[Human-centered design](https://jobicy.com/jobs?search_keywords=Human-centered%20design.md)[Content governance](https://jobicy.com/jobs?search_keywords=Content%20governance.md)[Localization](https://jobicy.com/jobs?search_keywords=Localization.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Stakeholder communication](https://jobicy.com/jobs?search_keywords=Stakeholder%20communication.md) Sample interview questionsHow would you approach content design for an AI-generated response in a complex work-management workflow?I would begin by identifying the user goal, decision point, and risks of an inaccurate or overly confident response. I would define content patterns for prompting, response structure, uncertainty, user controls, and recovery paths, then validate them through research and iteration with product and engineering. The final experience should make the AI useful while clearly communicating its role and limitations. Describe how you use research to inform UX content decisions. I combine qualitative feedback, usability findings, support trends, product analytics, and stakeholder context to understand where users hesitate or fail. I translate those insights into testable content hypotheses, such as simplifying terminology, improving hierarchy, or adding contextual guidance. I then validate the changes through usability testing or product metrics. How do you maintain consistency when creating content across a large product platform? I use a shared content system with principles, voice-and-tone guidance, terminology standards, reusable patterns, and documented decision criteria. I partner with design-system owners and other content practitioners to identify gaps and evolve the guidance. This creates consistent user experiences while allowing patterns to adapt to different product contexts. How would you explain and defend a content decision to a stakeholder who prefers different wording? I would connect the recommendation to user needs, product goals, research findings, and established content principles rather than frame it as a personal preference. I would present alternatives when appropriate and explain the trade-offs in clarity, accessibility, localization, and user trust. If uncertainty remains, I would propose a lightweight test to make the decision evidence-based. What considerations are important when writing content that must scale across languages and cultures? I avoid idioms, ambiguous phrasing, culturally specific references, and unnecessarily dense language. I design flexible UI strings that account for text expansion, grammatical differences, and context needs for translators. Early collaboration with localization partners helps ensure that the content remains understandable and respectful in every supported market. Opportunity details ## About this role. 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. #LI-Remote Show more [Apply now >](https://jobicy.com/jobs/156653-content-designer-ii-remote-eligible-costa-rica.md) > Annual salary information is not provided for this position. Explore salary ranges for similar roles in our [Salary Directory ›](https://jobicy.com/salaries.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. * ![Medium logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/10/WRILS-201015095329-656352.jpg) Medium Oct 23 New ### [Staff Product Designer](https://jobicy.com/jobs/156685-staff-product-designer-6.md) About Medium Medium is one of the world’s most influential writing platforms, connecting millions of readers with ideas that matter. We’re a small, dedicated team that cares deeply and takes… * ![PadSplit logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/06/da525286873130ed0b95212896ef55d4.jpg) PadSplit Oct 23 New ### [Senior Product Designer (Fully Remote – anywhere in South America)](https://jobicy.com/jobs/156673-senior-product-designer-fully-remote-anywhere-in-south-america.md) The Role We Need: PadSplit is hiring a Senior Product Designer to shape and improve experiences across our two-sided housing marketplace. Working on a growth-focused product team, you’ll tackle meaningful,… * ![TrustedHousesitters logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/42dad524-221.png) TrustedHousesitters Oct 23 New ### [Senior Product Designer – Growth](https://jobicy.com/jobs/156555-senior-product-designer-growth.md) Fully Remote (UK based) | Competitive Salary + Bonus + Generous Equity | B Corp Certified TrustedHousesitters is a fast growing, direct-to-consumer marketplace that is redefining pet care and travel…. * ![Monzo logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/5b4c0ec3-221.jpg) Monzo Oct 23 New ### [Lead Product Designer, Growth](https://jobicy.com/jobs/156510-lead-product-designer-growth.md) 🚀 We’re on a mission to make money work for everyone. We’re waving goodbye to the complicated and confusing ways of traditional banking. After starting as a prepaid card, our… * ![Monzo logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/5b4c0ec3-221.jpg) Monzo Oct 23 New ### [Lead Product Designer](https://jobicy.com/jobs/156508-lead-product-designer.md) 🚀 We’re on a mission to make money work for everyone. We’re waving goodbye to the complicated and confusing ways of traditional banking. After starting as a prepaid card, our… * ![Nextiva logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/5863278d-221.jpeg) Nextiva Oct 23 New ### [Senior Product Designer](https://jobicy.com/jobs/156503-senior-product-designer-16.md) Redefine the future of customer experiences. One conversation at a time. At Nextiva, we’re reimagining how businesses connect, bringing together customer experience and team collaboration on a single, conversation centric… * ![AlphaSense logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/01960e94-221.jpg) AlphaSense Oct 22 New ### [Senior/Staff Product Designer](https://jobicy.com/jobs/156358-senior-staff-product-designer.md) About AlphaSense: AlphaSense is the AI platform redefining market intelligence and workflow orchestration, trusted by thousands of leading organizations to drive faster, more confident decisions in business and finance. The… * ![Cloudbeds logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/3aef1a38-221.png) Cloudbeds Oct 22 Featured New ### [Website Onboarding Specialist](https://jobicy.com/jobs/156347-website-onboarding-specialist.md) What Makes Cloudbeds Unique At Cloudbeds, we’re not just building software, we’re transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to… * ![EverAI logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/91735b0b-221.png) EverAI Oct 22 New ### [Senior Product Designer (Full Remote – UK)](https://jobicy.com/jobs/153803-senior-product-designer-full-remote-uk.md) Our Vision & Products 🚀 EverAI — Building the Future of AI Companionship One of the Top 15 Largest & Fastest-Growing AI Companies in the World 50 Million Users in… * ![EverAI logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/91735b0b-221.png) EverAI Oct 22 New ### [Senior Product Designer (Full Remote – Netherlands)](https://jobicy.com/jobs/153798-senior-product-designer-full-remote-netherlands.md) Our Vision & Products 🚀 EverAI — Building the Future of AI Companionship One of the Top 15 Largest & Fastest-Growing AI Companies in the World 50 Million Users in… [Browse all jobs](https://jobicy.com/jobs.md)