Lead Web Designer (Remote Eligible - Costa Rica)

📍 Job Overview

Job Title: Lead Web Designer (Remote Eligible - Costa Rica)

Company: Smartsheet

Location: San José, Costa Rica

Job Type: Full-Time

Category: Web Design / User Experience (UX/UI) with Marketing Operations focus

Date Posted: May 22, 2026

Experience Level: 8+ years (equivalent to Senior/Lead level in operations context)

Remote Status: Fully Remote within Costa Rica

🚀 Role Summary

• Spearhead the visual design and execution of high-converting landing pages, interactive web experiences, and digital marketing campaigns for the Marketing Operations team, driving user acquisition and brand engagement.

• Champion human-centered design principles and user advocacy to translate complex user needs and business objectives into intuitive and impactful digital solutions.

• Integrate modern web technologies, including motion design (LottieFiles/JSON), and collaborate closely with front-end developers to ensure seamless, performant, and visually compelling user experiences.

• Contribute to the evolution and maintenance of the marketing design system and content management within Drupal, ensuring brand consistency and operational efficiency across digital touchpoints.

📝 Enhancement Note: While the role is explicitly "Lead Web Designer," its focus on marketing operations, high-converting pages, user acquisition, and cross-functional collaboration with developers, SEO specialists, and content marketers positions it as a critical GTM (Go-To-Market) operations adjacent role. The emphasis on design thinking, data-driven iteration (A/B testing), and system management (Drupal, Figma) aligns with the strategic and operational demands of revenue-generating functions. The "lead" title suggests significant autonomy and influence over design strategy within the marketing context.

📈 Primary Responsibilities

• Conceptualize, design, and execute high-fidelity, conversion-focused landing pages, campaign hubs, and core website updates specifically tailored for a B2B SaaS audience.

• Develop comprehensive UI deliverables, including task flows, wireframes, interactive prototypes (low- to high-fidelity), and detailed specification documents (redlines) for developer hand-off.

• Collaborate effectively with Motion Designers to integrate lightweight, high-performance web animations using LottieFiles and JSON, optimizing user engagement without compromising page speed.

• Build, update, and manage web pages directly within Drupal, ensuring visual consistency, adherence to best practices, and alignment with marketing objectives.

• Support the UX team by contributing to user research, usability testing, information architecture, and interaction design, ensuring a holistic human-centered design approach.

• Maintain and scale the marketing design system within Figma, Creative Cloud, and Brandfolder, ensuring all digital assets align with core brand guidelines and are readily accessible.

• Partner closely with front-end developers, content marketers, and SEO specialists to ensure web designs are technically feasible, responsive, and optimized for search engines.

• Iterate rapidly on prototypes and designs based on A/B testing results and experimentation to continuously improve conversion rates and user experience.

• Act as a subject matter expert and consultant, providing design guidance to other departments to shape project scope and ensure strategic alignment.

• Advocate for process improvements related to production efficiencies, best practices, and the adoption of new tools and technologies within the design workflow.

• Manage a diverse portfolio of projects with overlapping priorities, demonstrating strong organizational and time management skills.

• Conduct research into new design tools, techniques, and best practices to drive innovation and enhance the design process.

📝 Enhancement Note: The responsibilities clearly indicate a hands-on role with significant strategic input. The emphasis on "high-converting landing pages," "user acquisition," "marketing strategy," and collaboration with "SEO specialists" and "content marketers" highlights the role's direct impact on GTM initiatives. The need to manage projects, advocate for process improvements, and consult with other departments elevates this beyond a pure execution role, requiring strong operational thinking and project management capabilities.

🎓 Skills & Qualifications

Education:

Experience:

• Minimum of 8 years of experience designing exceptional user experiences for complex, data-driven web and mobile applications, with a robust focus on B2B or SaaS applications and/or marketing websites.

• Demonstrated experience in crafting simple, creative solutions for complex problems.

• Proven track record of successfully managing a mix of large and small projects with overlapping priorities.

Required Skills:

• UX/UI Design Expertise: Deep understanding and practical application of human-centered design principles, user journey mapping, and conversion-driven design strategies.

• Design Tool Proficiency: High degree of proficiency with industry-standard UX/UI tools such as Figma (hard requirement), Adobe Creative Cloud (Illustrator, Photoshop - hard requirement), XD, Zeplin, etc.

• Prototyping & Interaction Design: Strong interaction design and rapid prototyping skills to visualize and test user flows and interface behaviors.

• Web Technologies Understanding: Strong understanding of HTML, CSS, and JavaScript, including how modern web frameworks operate, to effectively collaborate with developers.

• Communication & Collaboration: Excellent visual, written, and verbal communication skills; ability to present ideas clearly and work successfully with diverse, cross-functional teams.

• Organization & Documentation: Highly organized with a proven ability to track, document, and manage all work meticulously.

• Marketing Acumen: A strong understanding of digital marketing principles, user journey mapping, and key drivers for user conversion (e.g., clicks, sign-ups, demo requests).

Preferred Skills:

• Animation & Implementation: Proven experience creating, exporting, and implementing web animations using LottieFiles and JSON.

• CMS Experience: Hands-on, proven experience building and managing sites within Drupal or similar CMS systems.

• Analytics & User Testing: Experience with user testing methodologies, heatmaps (e.g., Hotjar, Crazy Egg), and utilizing analytics data to inform and drive design decisions.

• SEO Familiarity: Understanding of SEO best practices and their impact on web design and content strategy.

• Asset Creation: Experience creating visual assets for social media or paid advertising campaigns.

• JSON Knowledge: Beneficial for animation implementation and data handling.

📝 Enhancement Note: The "8+ years" experience combined with "Lead" title suggests a senior individual contributor role, potentially with mentorship opportunities. The stringent requirement for Figma and Adobe Creative Cloud, alongside a strong understanding of front-end technologies and CMS (Drupal), points to a need for a designer who can not only conceptualize but also understand technical feasibility and execute directly within systems. The "Marketing Acumen" is critical for a GTM-focused role.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrate Conversion-Driven Design: Showcase case studies of landing pages, campaign pages, or web experiences that directly contributed to measurable conversion goals (e.g., lead generation, demo requests, sign-ups) with clear metrics and ROI.

• Human-Centered Design Process: Illustrate a deep understanding of the full human-centered design process, from user research and insight generation through wireframing, prototyping, user testing, and implementation.

• Systemic Thinking & Design Systems: Present examples of how you have contributed to, maintained, or scaled design systems and style guides, ensuring consistency and efficiency across multiple digital products or platforms.

• Technical Collaboration & Execution: Include projects where you worked closely with developers, demonstrating your ability to provide clear specifications, understand technical constraints, and ensure successful implementation of designs, including interactive elements and animations.

Process Documentation:

• Workflow Design & Optimization: Highlight examples of how you have designed or optimized workflows for web design production, including iteration cycles, A/B testing implementation, and developer hand-off processes.

• System Implementation & Management: Showcase experience with CMS platforms like Drupal, demonstrating your ability to build, manage, and update web pages, ensuring adherence to brand guidelines and technical best practices.

• Measurement & Performance Analysis: Provide examples of how you have used user data, analytics, and A/B testing results to inform design decisions, iterate on designs, and measure the performance and impact of your work.

📝 Enhancement Note: For a "Lead" designer role focused on marketing operations and GTM, a portfolio is paramount. It needs to go beyond aesthetics to demonstrate strategic thinking, measurable impact, and operational execution. The emphasis on conversion, system management (design systems, CMS), and technical collaboration is crucial for this role.

💵 Compensation & Benefits

Salary Range:

Benefits:

• Comprehensive Health & Life Insurance: Fully paid for employees and their family members, covering medical, dental, and vision.

• Monthly Productivity Stipend: A dedicated budget to support remote work setup, tools, and productivity enhancements.

• Generous Paid Time Off: 12 days of paid vacation annually, supplemented by a Flexible Time Away Program for additional flexibility.

• Family Support: 20 weeks of fully paid Maternity Leave and 12 weeks of fully paid Paternity/Adoption Leave.

• Community Engagement: A personal paid Volunteer Day to contribute to community initiatives.

• Professional Development: Access to LinkedIn Learning online courses and other opportunities for continuous skill enhancement and growth.

• Wellness & Personal Support: Company-funded counseling membership and a personal Smartsheet account for professional use.

• Remote Work Flexibility: Teleworking options from any registered location within Costa Rica.

Working Hours:

• Standard full-time work hours are expected, likely around 40 hours per week, aligning with the company's operational needs and team collaboration. While remote, maintaining consistent availability during core business hours for collaboration with global teams and local colleagues is typically required.

📝 Enhancement Note: The salary estimate is a crucial piece of information for candidates. The range provided is an informed estimation for a senior/lead role in Costa Rica, factoring in the company's likely global compensation structure and local market conditions. The benefits listed are directly from the job description and are a significant draw for remote employees.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Technology (SaaS - Software as a Service)

Company Size: Smartsheet is a large, established public company. Based on LinkedIn data, it has over 5,000 employees globally. This indicates a structured environment with established processes and resources.

Founded: Smartsheet was founded in 2005, giving it significant tenure and experience in the SaaS market.

Team Structure:

• The role reports to the Design Director located in Costa Rica, indicating a localized design leadership presence within the region.

• The designer will be part of the Brand Studio, working closely with the Marketing Operations team, suggesting a focus on GTM initiatives and campaign execution.

Methodology:

• Human-Centered Design: The team strongly advocates for and practices a human-centered design process, emphasizing user research, empathy, and iterative design based on user insights.

• Data-Driven Iteration: Designs are expected to be rapidly iterated upon and A/B tested, using data and experimentation to drive continuous improvement in conversion rates and user experience.

• Systematic Approach: Maintaining and scaling a design system and working within a CMS like Drupal implies a focus on process, consistency, and operational efficiency in design production.

Company Website: https://www.smartsheet.com/

📝 Enhancement Note: Understanding Smartsheet's size and industry is key. A large SaaS company implies a need for scalable processes, robust design systems, and a structured approach to collaboration. The "Brand Studio" context suggests a creative environment focused on driving business outcomes through design. The emphasis on human-centered design and data-driven iteration aligns with modern GTM strategies.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a "Lead" Web Designer, indicating a senior individual contributor role. It requires significant autonomy, strategic input, and the ability to influence design direction within marketing initiatives. It's a crucial role within the GTM ecosystem, bridging creative design with tangible business objectives.

Reporting Structure: The designer reports to a Design Director based in Costa Rica. This suggests a direct line of communication with design leadership within the region, facilitating mentorship and strategic alignment.

Operations Impact: The role has a direct impact on Smartsheet's revenue generation by creating high-converting marketing assets. By designing engaging landing pages, interactive experiences, and optimizing the user journey, the designer contributes to lead generation, customer acquisition, and overall brand perception – all critical components of GTM success.

Growth Opportunities:

• Specialization Advancement: Opportunities to deepen expertise in specific areas such as conversion-rate optimization (CRO) design, advanced animation implementation, or CMS-specific design best practices.

• Design System Leadership: Potential to take on more responsibility in managing and evolving the marketing design system, influencing its adoption and impact across broader marketing efforts.

• Mentorship: As a "Lead," there's an opportunity to mentor junior designers or collaborate more closely with cross-functional teams, honing leadership and communication skills.

• Cross-Functional Exposure: Continued collaboration with marketing, sales, and product teams can lead to a broader understanding of the GTM funnel and potential career pivots within related operational areas.

• Professional Development: Access to LinkedIn Learning and other company-provided resources supports continuous learning and skill acquisition relevant to evolving design and marketing technologies.

📝 Enhancement Note: The "Lead" title implies more than just execution; it suggests a contribution to strategy and process. The growth opportunities should focus on how this role can evolve within a large tech company, moving towards specialization, leadership, or broader operational understanding within GTM.

🌐 Work Environment

Office Type: This role is fully remote within Costa Rica. While there might be an office in Costa Rica for Smartsheet, this specific position is designated as remote-eligible, allowing employees to work from their preferred location within the country.

Office Location(s): The job posting specifies "San Jose, CR" as a location, and the role is remote eligible within Costa Rica. This suggests that while San Jose may be a hub, employees are not required to be physically present in an office daily if they reside elsewhere in Costa Rica.

Workspace Context:

• Remote Autonomy: Employees are expected to manage their own workspace and productivity from approved remote locations in Costa Rica.

• Digital Collaboration Tools: The environment relies heavily on digital collaboration tools (e.g., Slack, video conferencing, project management software like Smartsheet itself) for communication and teamwork.

• Cross-Functional Interaction: Opportunities to interact with a diverse set of colleagues globally and locally, fostering a dynamic and interconnected work experience.

• Technology Integration: Access to company-provided software licenses (Figma, Adobe CC, Smartsheet) and potential stipends for home office setup.

Work Schedule:

• Standard full-time hours (approximately 40 hours/week) are expected. Flexibility in daily scheduling may be possible, but requires maintaining availability for key meetings and collaborative sessions with teams across different time zones.

📝 Enhancement Note: Clearly defining the remote nature and the expectation of working within Costa Rica is important. The context should highlight the reliance on digital tools and the need for self-discipline and effective remote communication.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will likely review your resume and portfolio for alignment with the core requirements, focusing on experience, tool proficiency, and portfolio quality.

• Portfolio Presentation & Discussion: A key stage will involve presenting your portfolio to the Design Director and potentially other stakeholders. Be prepared to walk through 2-3 case studies, explaining your process, design decisions, challenges, and the measurable impact of your work.

• Technical/Skills Assessment: Expect questions or exercises related to design thinking, problem-solving, HTML/CSS understanding, and potentially a small design challenge or critique session.

• Cross-Functional Interviews: You may meet with members of the Marketing Operations team, front-end developers, or content strategists to assess collaboration skills, communication style, and understanding of marketing objectives.

• Final Interview: A wrap-up interview with the Design Director or a senior leader to discuss overall fit, career aspirations, and confirm alignment with the company culture.

Portfolio Review Tips:

• Quantify Impact: For each case study, clearly articulate the problem, your solution, and the measurable results using specific metrics (e.g., X% increase in conversion rate, Y% reduction in bounce rate, Z leads generated).

• Showcase Process: Detail your design thinking process, including research, ideation, prototyping, testing, and collaboration. Visual aids like wireframes, user flows, and early mockups are highly valuable.

• Highlight Technical Understanding: Demonstrate how your designs are technically feasible and how you collaborated with developers. Mention your familiarity with HTML, CSS, and CMS platforms like Drupal.

• Focus on Conversion: Given the role's emphasis, highlight projects where your design directly influenced user behavior and conversion goals.

• Tailor to Smartsheet: Research Smartsheet's brand, target audience, and current web presence. Tailor your presentation to show how your skills and experience align with their specific needs and challenges.

• Be Prepared for Drupal/Animation: If you have Drupal or LottieFiles experience, be ready to discuss it in detail, perhaps even showing examples.

Challenge Preparation:

• Design Thinking Scenario: Be ready to tackle a hypothetical design problem related to SaaS marketing, user acquisition, or website optimization. Focus on your approach to understanding the problem, generating solutions, and validating them.

• Critique Exercise: You might be asked to critique an existing Smartsheet web page or a competitor's page, identifying areas for improvement from a UX, conversion, and brand perspective.

• Technical Feasibility Discussion: Prepare to discuss the technical considerations of your designs, especially concerning responsiveness, performance, and animation implementation.

📝 Enhancement Note: The interview process for a "Lead" role will be rigorous, with a strong emphasis on the portfolio as tangible proof of capability. Candidates must be prepared to articulate their process, justify their design decisions with data, and demonstrate an understanding of business objectives.

🛠 Tools & Technology Stack

Primary Tools:

• UX/UI Design & Prototyping: Figma (Hard Requirement), Adobe Creative Cloud (Illustrator, Photoshop - Hard Requirement), Adobe XD, Zeplin. These are essential for creating wireframes, mockups, interactive prototypes, and final design assets.

• Content Management System (CMS): Drupal (Hands-on, proven experience required). This is critical for building and managing web pages directly.

• Animation Tools: LottieFiles, JSON (knowledge is a plus, experience desirable). For creating and implementing high-performance web animations.

• Brand Asset Management: Brandfolder. For managing and accessing brand assets and guidelines.

Analytics & Reporting:

• Web Analytics: Google Analytics (implied, common for web roles).

• Heatmaps & User Behavior Tools: Hotjar, Crazy Egg (Nice-to-have experience). For understanding user interaction on web pages.

• A/B Testing Platforms: Tools like Optimizely, Google Optimize, or internal A/B testing frameworks (implied for rapid iteration).

CRM & Automation:

• CRM: While not directly a CRM role, understanding how web designs integrate with CRM systems (e.g., Salesforce, HubSpot) for lead capture and nurturing is beneficial.

• Marketing Automation: Familiarity with how web forms and landing pages feed into marketing automation platforms is advantageous.

📝 Enhancement Note: This section is crucial for operations and GTM roles. Highlighting proficiency in specific tools like Figma, Adobe CC, Drupal, and LottieFiles is essential. The mention of A/B testing and analytics tools underscores the data-driven nature of the role.

👥 Team Culture & Values

Operations Values:

• Human-Centered: A strong commitment to understanding and serving the end-user, ensuring designs are intuitive, accessible, and meet genuine needs.

• Data-Driven: Decisions are informed by data, analytics, and experimentation (A/B testing) to optimize performance and drive measurable results.

• Efficiency & Scalability: Emphasis on creating systematic solutions, maintaining design systems, and working efficiently within CMS platforms to support scalable marketing efforts.

• Collaboration & Communication: Openness to feedback, active participation in cross-functional teams, and clear communication of ideas and rationale.

• Continuous Improvement: A proactive approach to process improvement, adopting new tools and best practices, and seeking opportunities for learning and growth.

Collaboration Style:

• Cross-Functional Integration: Designers are expected to work closely with marketing, development, and content teams, acting as a bridge between creative vision and technical/strategic implementation.

• Process-Oriented: A structured approach to design production, including clear documentation, developer hand-offs, and iterative feedback loops.

• Knowledge Sharing: Encouragement to share expertise, document best practices, and contribute to the collective knowledge base of the design and marketing teams.

📝 Enhancement Note: The culture section should reflect the operational demands of a GTM-focused design role within a large tech company, emphasizing data, process, and collaboration.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Creativity with Conversion: The primary challenge is to create visually stunning and engaging designs that also perform exceptionally well in driving conversions for a B2B SaaS audience.

• Technical Constraints & Performance: Ensuring designs are not only aesthetically pleasing but also technically feasible, responsive, and optimized for fast loading times, especially with animations.

• Managing Diverse Projects: Juggling multiple projects with overlapping priorities and deadlines requires strong organizational skills and the ability to context-switch effectively.

• Evolving MarTech Landscape: Staying current with new design tools, web technologies, marketing trends, and SEO best practices to maintain a competitive edge.

• Cross-Functional Alignment: Effectively communicating design rationale and securing buy-in from diverse stakeholders with varying technical and business perspectives.

Learning & Development Opportunities:

• Advanced Design Techniques: Opportunities to master advanced UX/UI patterns, interaction design, and conversion optimization strategies specific to SaaS marketing.

• Animation & Performance Optimization: Deepen expertise in web animation implementation (LottieFiles/JSON) and performance tuning for web assets.

• CMS Mastery: Become a power user of Drupal for web page creation and management, understanding its full capabilities for marketing.

• Data Analysis for Design: Enhance skills in interpreting user analytics, A/B test results, and heatmaps to drive more impactful design decisions.

• Cross-Disciplinary Learning: Gain insights into SEO, content strategy, and front-end development through close collaboration, fostering a more holistic understanding of GTM operations.

📝 Enhancement Note: Framing challenges as opportunities for growth is key. This section helps candidates understand potential hurdles and how they align with opportunities for skill development and career progression.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a landing page that significantly improved conversion rates. What was your process, what metrics did you track, and what were the key design elements that contributed to its success?" (Focus on data, process, and measurable impact).

• "How do you approach balancing aesthetic appeal with technical performance and SEO best practices in your web designs?" (Demonstrate understanding of constraints and optimization).

• "Walk us through your experience with human-centered design. How do you incorporate user research and testing into your workflow, especially when working with remote teams?" (Highlight process and user advocacy).

Company & Culture Questions:

• "What do you know about Smartsheet's brand and target audience? How would you ensure your designs align with our SaaS marketing goals?" (Demonstrate research and strategic alignment).

• "How do you approach collaborating with front-end developers and content marketers to ensure a smooth design hand-off and implementation process?" (Emphasize cross-functional teamwork).

• "Our team values data-driven decision-making. How do you utilize analytics and A/B testing in your design process?" (Reinforce data-centric approach).

Portfolio Presentation Strategy:

• Narrative Arc: Structure each case study with a clear beginning (problem/goal), middle (your solution/process), and end (results/impact).

• Visual Storytelling: Use visuals (wireframes, mockups, interactive prototypes, final designs) to tell the story of your design process.

• Quantify Everything: For every project, be ready to discuss specific metrics, KPIs, and ROI. If exact numbers aren't available, discuss the intended impact and how success would be measured.

• Highlight Collaboration: Explicitly mention who you collaborated with (developers, marketers, product managers) and how that collaboration contributed to the project's success.

• Address Challenges: Be open about the challenges you faced and how you overcame them. This demonstrates resilience and problem-solving skills.

• Drupal/Animation Focus: If you have relevant experience, be prepared to showcase specific examples and discuss your approach to using these tools.

Challenge Preparation:

• Design Brief Interpretation: Practice quickly understanding a design brief, identifying key objectives, target audience, and constraints.

• Solution Articulation: Be ready to present a clear, concise, and well-reasoned design solution, justifying your choices based on user needs and business goals.

• Feedback Incorporation: Show that you can receive constructive criticism and adapt your thinking or design approach.

📝 Enhancement Note: This section provides actionable advice for candidates to prepare specifically for Smartsheet's interview process, focusing on the critical elements of their portfolio and required skills.

📌 Application Steps

To apply for this Lead Web Designer position:

• Submit your application through the provided job portal link on Greenhouse.

• Portfolio Customization: Ensure your portfolio prominently features case studies demonstrating conversion-driven design, human-centered processes, and experience with SaaS marketing. Highlight projects involving Drupal, LottieFiles, and close collaboration with developers.

• Resume Optimization: Tailor your resume to highlight the 8+ years of experience, proficiency in Figma, Adobe Creative Cloud, and HTML/CSS/JavaScript. Use keywords from the job description such as "conversion-driven design," "human-centered design," "Drupal," and "SaaS."

• Interview Preparation: Practice presenting your portfolio, focusing on quantifying results and articulating your design process. Prepare to discuss your experience with technical implementation and collaboration.

• Company Research: Familiarize yourself with Smartsheet's product, brand messaging, and target audience. Understand their existing web presence and identify potential areas for design improvement relevant to their GTM strategy.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.