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: Marketing Operations / Web Design

Date Posted: March 20, 2026

Experience Level: 10+ Years

Remote Status: Remote Eligible (Must reside in Costa Rica)

🚀 Role Summary

• Drive visual strategy for marketing initiatives, focusing on high-converting landing pages, interactive web experiences, and engaging digital campaigns.

• Conceptualize and execute user-centered designs, translating user and business data into task flows, wireframes, and interactive prototypes.

• Collaborate closely with front-end developers, content marketers, and SEO specialists to ensure technically feasible, responsive, and optimized web designs.

• Maintain and scale the marketing design system, ensuring visual consistency and adherence to brand guidelines across various digital touchpoints.

• Actively research and advocate for process improvements in production efficiencies and best practices within the design and web development lifecycle.

📝 Enhancement Note: This role is positioned as a "Lead" Web Designer, implying a senior level of expertise and responsibility. The emphasis on "Marketing Operations team" and "Marketing strategy" alongside "user acquisition" suggests a strong focus on conversion rate optimization (CRO) and demand generation through web presence. The requirement to reside in Costa Rica is a critical logistical detail for remote eligibility.

📈 Primary Responsibilities

• Serve as the primary visual architect for marketing product representation, conceptualizing and crafting high-converting landing pages, interactive web experiences, and compelling digital campaigns.

• Develop comprehensive task flows, wireframes, and low-to-high-fidelity interactive prototypes, rigorously grounded in user insights and business objectives.

• Provide detailed assets, specifications, and clear guidance for UI implementation throughout the entire development lifecycle, ensuring seamless developer hand-off.

• Execute rapid iteration cycles on prototypes and designs to support A/B testing and experimentation, optimizing for user engagement and conversion.

• Uphold and enhance existing design patterns and style guides, contributing to the evolution of the brand's visual language.

• Generate meticulous UI deliverables and specification documents, including detailed redlines, to facilitate efficient and accurate implementation by developers.

• Actively support the broader UX team by contributing to user research, usability testing, information architecture, and interaction design efforts.

• Foster effective collaboration and communication across diverse teams and departments to achieve shared project goals.

• Design user experiences across both digital and physical touchpoints, ensuring strict adherence to established style guides and design systems.

• Share and document knowledge, perspectives, and best practices with design peers and the wider team.

• Champion and implement process improvements aimed at enhancing production efficiencies and adopting industry best practices.

• Effectively manage a diverse project portfolio, balancing large-scale initiatives with smaller, high-priority tasks.

• Proactively research and integrate new tools and methodologies to adapt to the evolving landscape of web design and user experience.

• Engage with various departments to deeply understand user needs and goals, translating these into actionable design strategies for cross-functional product teams.

• Design high-fidelity, conversion-focused landing pages, campaign hubs, and core website updates specifically tailored for a SaaS target audience, with supplementary in-app graphics as needed.

• Collaborate with Motion Designers to create and implement lightweight, high-performance web animations using LottieFiles and JSON, ensuring enhanced user engagement without compromising page speed.

• Build, update, and manage web pages directly within Drupal, guaranteeing visual consistency and adherence to established best practices.

• Contribute to the maintenance and scaling of the marketing design system within Figma, Creative Cloud, and Brandfolder, ensuring all assets align with core brand guidelines.

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

• Network with peers and stakeholders to drive technology and UI improvements that enhance the overall web presence.

• Act as a subject matter expert, consulting with other departments to shape project scope and technical requirements related to web design.

• Undertake other assigned job duties as required.

📝 Enhancement Note: The responsibilities highlight a blend of strategic design leadership, hands-on execution, and technical understanding. The emphasis on "high-converting landing pages," "conversion-driven design," "A/B testing," and "Marketing Acumen" strongly indicates this role is deeply embedded within a demand generation and customer acquisition framework, requiring a results-oriented approach rather than purely aesthetic design. The mention of Drupal and LottieFiles points to specific technical execution requirements.

🎓 Skills & Qualifications

Education: Academic studies/certifications or relevant experience in Design Thinking, Human-Centered Design, and UX/UI Design are considered a plus.

Experience: 8+ years of experience designing exceptional experiences for complex, data-driven web and mobile applications, with a strong emphasis on B2B or SaaS applications and/or marketing websites.

Required Skills:

• Proven track record for crafting simple, creative solutions for complex problems, demonstrating a sophisticated understanding of the full human-centered design process.

• Stellar portfolio showcasing a keen eye for typography, layout, conversion-driven design principles, and interactive web elements.

• Strong interaction design and advanced prototyping skills.

• High degree of proficiency with UX/UI tools such as Figma, Adobe XD, or Zeplin.

• Hard requirement for proficiency in design tools like Adobe Illustrator and Adobe Photoshop.

• Strong understanding of foundational web technologies including HTML, CSS, and JavaScript.

• Excellent communication and interpersonal skills, encompassing visual, written, verbal, and presentation abilities, with a demonstrated capacity to work successfully with diverse, cross-functional teams.

• Highly organized with the ability to track, document, and manage all work meticulously.

• Hands-on, proven experience building and managing websites within Drupal or similar Content Management Systems (CMS).

Preferred Skills:

• Experience with user testing methodologies, heatmap analysis tools (e.g., Hotjar, CrazyEgg), and leveraging analytics data to inform and drive design decisions.

• Familiarity with Search Engine Optimization (SEO) best practices and their impact on web design strategies.

• Experience creating digital assets for social media platforms or paid advertising campaigns.

• Proven experience creating, exporting, and implementing web animations using LottieFiles and JSON.

• Knowledge of JSON is considered a plus.

📝 Enhancement Note: The "8+ years" requirement, combined with the "Lead" title, suggests a senior-level candidate expected to mentor junior designers and influence strategic decisions. The explicit mention of "conversion-driven design" and "Marketing Acumen" elevates this beyond a typical UI/UX role, emphasizing a direct contribution to business growth and lead generation. The requirement for HTML/CSS/JavaScript knowledge, alongside CMS experience (Drupal), indicates the need for a designer with a strong technical understanding, capable of bridging the gap between design and implementation.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least 3-5 significant projects demonstrating complex problem-solving within B2B/SaaS web applications or marketing websites.

• Highlight your role and specific contributions to each project, particularly in areas of user research, wireframing, prototyping, UI design, and A/B testing.

• Include detailed examples of conversion-driven design strategies and how they directly impacted user acquisition or engagement metrics.

• Present case studies that clearly articulate the design process, the challenges faced, the solutions implemented, and the measurable outcomes achieved.

Process Documentation:

• Provide examples of how you have documented design processes, including user flows, wireframes, and UI specifications for developer hand-off.

• Showcase instances where you have contributed to or improved design systems, style guides, or pattern libraries.

• Illustrate your approach to A/B testing and iteration, including how you use data to inform design changes and optimize user experiences.

• Present documentation related to your experience with CMS platforms like Drupal, detailing how you managed content and design implementation.

📝 Enhancement Note: Given the emphasis on conversion, A/B testing, and technical implementation (Drupal, HTML/CSS/JS), the portfolio should strongly feature case studies that quantify the impact of design decisions on business metrics. The "Lead" designation implies the portfolio should also hint at strategic thinking, process improvement advocacy, and perhaps mentorship or guiding junior designers.

💵 Compensation & Benefits

Salary Range:

Based on industry benchmarks for a Lead Web Designer role with 8+ years of experience in a high-cost-of-living region like San José, Costa Rica, and considering Smartsheet's standing as a well-established SaaS company, the estimated annual salary range is between $60,000 - $90,000 USD. This estimate accounts for the required technical and strategic skills, the remote work arrangement, and the specific demands of a marketing-focused web design role.

Benefits:

• Fully paid Health & Life insurance for employees and their family members.

• Monthly stipend to support work-related expenses and productivity.

• Generous Paid Vacation: 12 days per year, complemented by a Flexible Time Away Program.

• Comprehensive Paid Parental Leave: 20 weeks for maternity and 12 weeks for paternity/adoption.

• Personal Paid Volunteer Day to contribute to community initiatives.

• Opportunities for continuous professional growth and development, including access to LinkedIn Learning courses.

• Company-funded perks such as a counseling membership and a personal Smartsheet account.

Working Hours:

The role is based on a standard 40-hour work week, with flexibility offered to accommodate the remote work arrangement and potential project demands.

📝 Enhancement Note: The salary range is an estimation based on the role's seniority, location (San José, Costa Rica, which has a moderate cost of living compared to major US tech hubs but is a significant market for local talent), and the company's industry. The benefits package is robust and competitive, reflecting typical offerings for well-funded tech companies, with specific emphasis on parental leave and professional development, which are attractive to experienced professionals.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Cloud Computing / SaaS (Software as a Service)

Company Size: Smartsheet is a large, publicly traded company with over 1,000 employees (as of recent public data), indicating a structured, established corporate environment with significant resources and established processes.

Founded: Smartsheet was founded in 2005, signifying a mature company with a long history of product development and market presence.

Team Structure:

• The role reports to the Design Director and is part of the Marketing Operations team, suggesting a close working relationship with marketing strategists, content creators, and potentially sales enablement functions.

• The team likely comprises specialists in various design disciplines (UX, UI, Motion, Web), content, SEO, and marketing analytics, fostering a collaborative environment for campaign execution and optimization.

Methodology:

• Data Analysis & Insights: A strong emphasis on leveraging user data, A/B testing results, and marketing analytics to inform design decisions and measure campaign effectiveness.

• Workflow Planning & Optimization: Focus on designing efficient workflows for campaign creation, landing page development, and iterative design improvements, ensuring both speed and quality.

• Automation & Efficiency: Adoption of modern tools and practices (e.g., design systems, LottieFiles, Drupal CMS) to streamline production processes and enhance output.

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

📝 Enhancement Note: Smartsheet's established presence and public company status suggest a culture that balances innovation with structured processes. The integration within "Marketing Operations" points to a data-driven, results-oriented approach where design directly contributes to measurable business outcomes like lead generation and customer acquisition. The mention of "magic at work" and "space to think big" suggests an aspirational culture that encourages creativity and impact.

📈 Career & Growth Analysis

Operations Career Level: This "Lead Web Designer" role represents a senior individual contributor position. It signifies a level of expertise where the individual is expected to not only execute complex design tasks but also to influence design strategy, mentor junior team members, and champion best practices within the marketing operations and design functions. The role requires a blend of deep technical design skills and a strategic understanding of marketing objectives.

Reporting Structure: The role reports to the Design Director, with potential for direct interaction with Marketing Operations leadership and cross-functional stakeholders across product marketing, development, and content teams. This structure allows for both specialized design guidance and broad business context.

Operations Impact: The Lead Web Designer's impact is directly tied to Smartsheet's customer acquisition and revenue generation efforts. By creating high-converting web experiences, interactive campaigns, and optimized landing pages, this role directly influences lead quality, conversion rates, and ultimately, customer acquisition cost and pipeline growth. Their work is crucial for translating marketing strategies into tangible user engagement and business results.

Growth Opportunities:

• Operations Skill Advancement: Deepen expertise in conversion rate optimization (CRO), SaaS marketing best practices, and advanced web animation techniques.

• Leadership Development: Potential to move into a Design Manager role, overseeing a team of designers, or specialize further in areas like UX strategy or design systems architecture.

• Cross-Functional Impact: Gain experience influencing broader Go-To-Market (GTM) strategies through data-driven web design insights and collaboration with marketing, sales, and product teams.

• Industry Recognition: Contribute to high-profile marketing campaigns for a leading SaaS company, building a strong professional portfolio and reputation.

📝 Enhancement Note: The "Lead" title and the emphasis on conversion, marketing strategy, and influencing across departments suggest significant growth potential beyond individual contribution, possibly into management or specialized strategic roles within the GTM operations sphere. The mention of "marketing design system" also points to opportunities in design operations and governance.

🌐 Work Environment

Office Type: While the role is remote eligible, Smartsheet maintains physical office locations. The remote work arrangement from Costa Rica implies a focus on asynchronous communication and digital collaboration tools, with potential for occasional virtual or in-person team gatherings if feasible within the company's structure.

Office Location(s): The primary reference is San José, Costa Rica, implying that candidates must reside within Costa Rica to be eligible for this remote position. Smartsheet has global offices, but this specific role is tied to the Costa Rican talent pool for remote work.

Workspace Context:

• Collaborative Environment: Expect a highly collaborative digital workspace, utilizing tools like Slack, Zoom, and shared project management platforms to connect with a dispersed team.

• Operations Tools & Technology: Access to industry-standard design software (Figma, Adobe Creative Suite), CMS platforms (Drupal), animation tools (LottieFiles), and collaboration suites is expected.

• Team Interaction: Regular virtual meetings, design critiques, and cross-functional syncs will be key to staying aligned and ensuring project success. Opportunities for knowledge sharing through internal documentation and presentations are likely.

Work Schedule: A standard 40-hour work week is expected, with flexibility for remote work. This allows for efficient management of design tasks, collaboration with global teams across different time zones, and dedicated time for deep work, A/B testing analysis, and iterative design.

📝 Enhancement Note: The remote aspect in Costa Rica suggests the company is leveraging international talent. The "workspace context" emphasizes the digital nature of this role and the reliance on robust communication and collaboration tools, typical for modern remote GTM operations.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review applications and portfolios, focusing on experience alignment, skill relevance (especially Figma, Adobe Suite, HTML/CSS/JS), and the quality of design work demonstrated.

• Design Challenge / Portfolio Review: Candidates will likely present their portfolio, discussing specific projects, design rationale, and their approach to conversion optimization, A/B testing, and technical implementation. A practical design exercise or case study may be assigned to assess problem-solving skills and design execution under pressure.

• Team/Stakeholder Interviews: Interviews with the Design Director, fellow designers, and key marketing operations stakeholders to assess collaboration style, communication skills, strategic thinking, and cultural fit. Expect questions related to human-centered design, managing priorities, and working with developers.

• Final Interview: Potentially with higher-level management to discuss overall fit, leadership potential, and long-term vision alignment.

Portfolio Review Tips:

• Quantify Impact: Clearly articulate the business impact of your designs. Use metrics related to conversion rates, engagement, lead generation, or A/B test results.

• Showcase Process: Detail your thought process, from initial brief and research to wireframing, prototyping, user testing, and final implementation. Highlight how you integrated user feedback and data.

• Technical Integration: Emphasize projects where you collaborated closely with developers, showcasing your understanding of HTML, CSS, JavaScript, and CMS capabilities (especially Drupal). Explain how you ensured designs were technically feasible and optimized for performance.

• Conversion Focus: Dedicate sections to projects that specifically demonstrate your ability to design for conversion. Explain the strategies you employed and the rationale behind them.

• Visual Storytelling: Present your work clearly and concisely. Use high-quality visuals and compelling narratives to showcase your best projects. Ensure your portfolio is easily navigable and highlights your strongest work first.

Challenge Preparation:

• Design for Conversion: Be prepared for challenges that require designing a landing page or campaign element for a specific SaaS product, focusing on driving a defined action (e.g., demo request, trial signup).

• Problem-Solving Scenarios: Anticipate questions about how you would approach improving a low-converting landing page or designing a new interactive feature. Focus on your process and data-driven approach.

• Technical Constraints: Consider how you would adapt designs for performance, responsiveness, and integration with a CMS like Drupal.

📝 Enhancement Note: The emphasis on a portfolio review and potential design challenge underscores the practical, execution-oriented nature of this role. Candidates should prepare to walk through their work and discuss their design decisions in the context of marketing goals and technical constraints. Explicitly preparing for "conversion-driven design" and "collaboration with developers" is key.

🛠 Tools & Technology Stack

Primary Tools:

• UX/UI Design: Figma (primary), Adobe XD, Zeplin.

• Graphic Design: Adobe Illustrator, Adobe Photoshop.

• Prototyping: Figma (integrated), potentially others.

• CMS: Drupal (hands-on experience required for building/managing pages).

Analytics & Reporting:

• Web Analytics: Google Analytics (assumed, given SaaS context), Hotjar, CrazyEgg (preferred for heatmaps/user behavior analysis).

• A/B Testing Tools: Google Optimize, Optimizely, or similar platforms for rapid experimentation.

CRM & Automation:

• CRM: Smartsheet itself likely integrates with various CRMs (e.g., Salesforce, HubSpot), understanding how web experiences feed into CRM data pipelines is beneficial.

• Animation: LottieFiles, JSON for implementing web animations.

• Asset Management: Brandfolder (for maintaining design system assets).

📝 Enhancement Note: Proficiency with Figma and Adobe Creative Suite is a hard requirement. Hands-on experience with Drupal for web page management is critical. The inclusion of LottieFiles and JSON for animation indicates a need for designers who can work with modern, efficient animation technologies. Familiarity with analytics and A/B testing tools is highly desired for driving data-informed design.

👥 Team Culture & Values

Operations Values:

• Data-Driven Decision Making: A strong reliance on user data, analytics, and A/B testing results to guide design choices and measure success. Operations professionals are expected to champion data integrity and insights.

• Efficiency & Optimization: A continuous drive to improve processes, streamline workflows, and optimize outcomes, whether in design production, campaign execution, or user experience.

• Collaboration & Transparency: Open communication, knowledge sharing, and a willingness to work collaboratively across departments to achieve common goals.

• User-Centricity: A deep commitment to understanding and advocating for the end-user, ensuring that designs are intuitive, valuable, and meet user needs effectively.

• Innovation & Adaptability: An openness to exploring new tools, technologies, and methodologies to stay ahead in the evolving digital landscape.

Collaboration Style:

• Cross-Functional Integration: Expect frequent collaboration with marketing, content, SEO, and development teams. The ability to translate design concepts into actionable tasks for these teams is crucial.

• Feedback & Iteration: A culture that encourages constructive feedback on designs and embraces iterative improvements based on testing and stakeholder input.

• Knowledge Sharing: Opportunities to share expertise through presentations, documentation, and participation in design reviews, contributing to the collective learning of the operations and marketing teams.

📝 Enhancement Note: The company culture appears to value a blend of analytical rigor (data-driven, optimization) and creative innovation (user-centricity, adaptability). For operations roles, this translates to a need for individuals who can balance strategic thinking with meticulous execution and effective teamwork.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Creative Vision with Technical Constraints: Effectively translating innovative design concepts into feasible web implementations within the constraints of Drupal, performance budgets, and existing codebases, while collaborating closely with developers.

• Driving Conversion in a Competitive SaaS Market: Continuously optimizing web experiences to stand out in a crowded SaaS landscape and achieve ambitious lead generation and customer acquisition targets.

• Managing Multiple Priorities and Stakeholders: Juggling a diverse project load with overlapping deadlines and competing stakeholder needs, requiring strong organizational and prioritization skills.

• Staying Ahead of Web Design Trends and Technologies: Keeping pace with rapid advancements in web design, animation, and user experience best practices, and integrating them effectively into Smartsheet's web presence.

Learning & Development Opportunities:

• Advanced Design Skills: Opportunities to hone skills in motion design (LottieFiles), advanced prototyping, and potentially explore areas like UX research or design systems architecture.

• Marketing & GTM Strategy: Deepen understanding of SaaS marketing principles, SEO, A/B testing strategy, and how web design directly impacts Go-To-Market initiatives.

• Technical Acumen: Enhance knowledge of front-end development principles, CMS capabilities (especially Drupal), and web performance optimization.

• Leadership & Mentorship: Potential to mentor junior designers, lead design initiatives, and influence strategic design decisions within the marketing operations team.

📝 Enhancement Note: The challenges are typical for a senior designer in a fast-paced tech environment, emphasizing the need for adaptability, strong technical understanding, and strategic alignment with business goals. The growth opportunities are clearly defined, offering paths for both specialization and leadership within the operations and design fields.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a landing page or web experience that significantly improved conversion rates. What was your process, what data did you use, and what were the key learnings?" (Focus on quantifiable results and data-driven design).

• "How do you approach balancing creative innovation with the technical constraints of a CMS like Drupal and front-end development limitations? Provide an example." (Highlight your understanding of implementation and collaboration).

Company & Culture Questions:

• "What excites you about Smartsheet's product and its mission? How do you see your design expertise contributing to our GTM strategy?" (Showcase your research and alignment with company goals).

• "How do you foster collaboration with cross-functional teams, particularly developers and content marketers? Describe a challenging collaboration and how you navigated it." (Assess your teamwork and communication skills).

Portfolio Presentation Strategy:

• Structure for Impact: Begin with your strongest, most relevant projects that showcase conversion-driven design and technical execution.

• Tell a Story: For each project, clearly articulate the problem, your role, your design process, the challenges overcome, and the measurable results achieved.

• Highlight Data & Metrics: Be prepared to discuss the specific metrics that influenced your design decisions and the impact your designs had on business outcomes (e.g., conversion rates, user engagement, lead generation).

• Demonstrate Technical Understanding: Explain how your designs were implemented, your collaboration with developers, and any considerations for performance, responsiveness, and CMS integration.

• Address "Lead" Responsibilities: Briefly touch upon how you've influenced design direction, mentored others, or advocated for process improvements in past roles.

📝 Enhancement Note: Interview preparation should focus on demonstrating a blend of creative design talent, strategic marketing understanding, technical execution capabilities, and strong collaborative skills. Candidates must be ready to back up their portfolio with data and specific examples of problem-solving and impact.

📌 Application Steps

To apply for this Lead Web Designer position:

• Submit your application through the provided link on the greenhouse job board.

• Customize Your Resume: Tailor your resume to highlight the 8+ years of experience, specific skills (Figma, Adobe Suite, HTML/CSS/JS, Drupal, LottieFiles), and achievements related to conversion optimization, SaaS marketing websites, and interactive web experiences. Use keywords from the job description.

• Curate Your Portfolio: Ensure your portfolio prominently features case studies demonstrating your proficiency in conversion-driven design, user-centered processes, A/B testing, and technical implementation. Quantify results wherever possible and clearly label your role in each project.

• Prepare Your Presentation: Practice walking through your portfolio with a focus on storytelling, highlighting your problem-solving approach, and discussing the business impact of your design decisions. Be ready to discuss your experience with Drupal and modern animation techniques.

• Research Smartsheet: Familiarize yourself with Smartsheet's product, its target audience, and its current web presence. Understand their marketing messaging and identify potential design opportunities or areas for improvement.

⚠️ 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.