Lead Visual Designer (Remote eligible - Costa Rica)

📍 Job Overview

Job Title: Lead Visual Designer (Remote eligible)

Company: Smartsheet

Location: San José, Costa Rica

Job Type: Full-Time

Category: Visual Design / Brand Strategy

Date Posted: March 19, 2026

Experience Level: 10+ Years

Remote Status: Fully Remote (within Costa Rica)

🚀 Role Summary

• Spearhead visual design initiatives to elevate the Smartsheet brand, ensuring clear communication and user delight through innovative concepts and flawless execution.

• Contribute to the definition, creation, and maintenance of robust design systems, component libraries, and comprehensive brand guidelines to ensure consistency and scalability across all touchpoints.

• Provide leadership and mentorship to a team of designers, conducting thorough reviews to uphold world-class quality standards and foster professional development.

• Manage the complete project lifecycle from conception to final delivery with minimal supervision, taking ownership of both the strategic 'how' and the tactical 'when'.

• Demonstrate strategic foresight by aligning creative solutions with specific business needs and organizational resources, acting as a proactive partner to stakeholders.

📝 Enhancement Note: This role is designated as a Lead Visual Designer, indicating a senior-level position requiring not only expert design skills but also leadership, strategic thinking, and the ability to manage complex projects and teams. The emphasis on "conceptual powerhouse" and "idea engine" suggests a need for highly creative individuals capable of driving brand evolution and system definition. The remote eligibility is strictly within Costa Rica, requiring candidates to reside there.

📈 Primary Responsibilities

• Drive Brand Evolution: Develop and execute net-new visual design directions with the explicit goal of elevating the Smartsheet brand identity and user experience across all platforms.

• Master & Maintain Design Systems: Actively participate in defining, creating, and maintaining flexible and scalable design systems, component libraries, and detailed brand guidance documents.

• Lead & Mentor Other Designers: Provide guidance, constructive feedback, and project oversight to junior and mid-level designers, ensuring adherence to brand standards and professional growth.

• Own Project Lifecycles: Take full responsibility for managing projects from initial concept through final execution, including defining project scope, timelines, and deliverables with minimal direction.

• Manage Multiple Projects: Expertly juggle several medium-to-large scale design projects simultaneously, ensuring all deadlines are met and helping less experienced designers manage their time and resources effectively.

• Collaborate as a Strategic Partner: Act as a project owner who shares equal investment in a stakeholder’s project goals, focusing on business outcomes in addition to visual output.

• Present & Persuade Effectively: Confidently present design work to various internal teams and leadership, structuring presentations clearly to solicit targeted feedback and maintain project alignment.

• Commission External Specialists: Identify, vet, and commission external creative talent (e.g., artists, photographers) to enhance unique, high-impact projects and bring fresh perspectives.

📝 Enhancement Note: The responsibilities highlight a blend of hands-on design execution and leadership, emphasizing ownership, strategic thinking, and cross-functional collaboration. The inclusion of "Commission Excellence" points to an art direction capability for specific project needs.

🎓 Skills & Qualifications

Education:

• Bachelor’s degree in Design, Graphic Design, Visual Communications, or a related field.

Experience:

• A minimum of 10 years of progressive experience in mid-to-senior level visual design roles, with a significant focus on marketing collateral, brand systems, and digital strategy.

• Proven experience working within the Technology sector is highly preferred.

Required Skills:

• Strategic Foresight: Ability to understand the broader business objectives and translate them into effective visual design solutions that align with organizational resources.

• Proactive Ownership & Collaboration: A demonstrated habit of anticipating stakeholder needs and collaborating as a peer to achieve optimal project outcomes.

• Expert Craftsmanship in Adobe Creative Suite: Mastery of core Adobe tools including Illustrator, Photoshop, InDesign, Creative Cloud, Firefly, and Express.

• Design System Proficiency: Experience in defining, building, and maintaining design systems, component libraries, and brand style guides.

• Presentation & Communication: Exceptional ability to present design concepts clearly and persuasively to diverse audiences, including executive leadership.

• Project Management: Proven ability to manage multiple complex projects simultaneously, meet deadlines, and oversee timelines effectively.

Preferred Skills:

• Motion Graphics: Experience with After Effects for creating dynamic visual content.

• Document Design: Proficiency in designing for Google Workspace and Microsoft Office suites.

• Web Design Tools: Familiarity with Figma, Zeplin, Webflow.

• Web Technologies: Basic understanding of HTML/CSS.

• Content Management Systems: Experience with platforms like Drupal.

• AI Design Tools: Experience with Generative AI and Agentic AI in a design context.

📝 Enhancement Note: The requirements emphasize a senior-level individual with a strong blend of technical design skills, strategic thinking, leadership potential, and experience in the tech industry. The bonus skills indicate a desire for a versatile designer capable of contributing across various media and platforms.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrated Brand Evolution: Showcase a portfolio that clearly illustrates your ability to elevate and evolve brand identities through strategic visual design, including before-and-after examples if possible.

• Design System Examples: Include case studies or examples of design systems, component libraries, or style guides you have developed or significantly contributed to, highlighting their structure and impact.

• End-to-End Project Ownership: Present projects that demonstrate your full involvement from concept development to final execution, detailing your role, process, and the outcomes achieved.

• Cross-Functional Collaboration: Provide examples where you effectively collaborated with stakeholders (e.g., marketing, product, engineering) to achieve business objectives through design.

• Problem/Solution Framework: For each key project, clearly articulate the problem statement, your strategic approach, the design solutions implemented, and the measurable results or impact.

Process Documentation:

• Clearly outline your design process for key projects, from initial briefing and research through ideation, iteration, final delivery, and system implementation.

• Demonstrate how you approach the creation and maintenance of design systems, including version control, documentation, and feedback loops.

• Illustrate your methods for conducting design reviews, providing constructive feedback, and ensuring quality and brand consistency across a team's output.

📝 Enhancement Note: For a Lead Visual Designer role, the portfolio is paramount. It needs to go beyond just aesthetic appeal to demonstrate strategic thinking, process rigor, system understanding, and leadership capabilities. Emphasis on measurable impact and collaborative approach is crucial.

💵 Compensation & Benefits

Salary Range:

Benefits:

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

• Monthly Stipend: A dedicated allowance to support remote work setup and ongoing productivity.

• Generous Paid Time Off: 12 days of paid vacation plus a Flexible Time Away Program for work-life balance.

• Comprehensive Parental Leave: 20 weeks fully paid Maternity Leave and 12 weeks fully paid Paternity/Adoption Leave.

• Community Engagement: Personal paid Volunteer Day to contribute to local communities.

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

• Wellness Support: Company-funded perks including a counseling membership and a personal Smartsheet account.

Working Hours:

• Standard full-time role, typically around 40 hours per week. While remote, adherence to core business hours for collaboration with global teams may be expected, with flexibility offered within the Costa Rican time zone.

📝 Enhancement Note: The salary range is an estimation based on publicly available data for similar roles and locations, factoring in the senior leadership aspect and the specific benefits package offered. The benefits are comprehensive and reflect a strong commitment to employee well-being and professional growth.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software as a Service (SaaS), Work Management Software. Smartsheet operates in a competitive but growing market, focusing on empowering teams with dynamic work management solutions. This context means design plays a crucial role in user adoption, brand perception, and differentiating from competitors.

Company Size: Smartsheet is a publicly traded company (SMAR) with a significant global presence, indicating a structured yet dynamic corporate environment. This size suggests ample resources for design initiatives and opportunities for impact, but also a need for clear processes and brand consistency.

Founded: Smartsheet was founded in 2005. This history implies a company with established processes, a proven product-market fit, and a culture that has evolved over time to support growth and innovation.

Team Structure:

• The Lead Visual Designer will report to the Creative Director based in Costa Rica, indicating a regional creative hub.

• The role involves leading and mentoring other designers, suggesting a team structure where this position acts as a senior individual contributor and informal team lead.

Methodology:

• Smartsheet's approach likely emphasizes data-driven decision-making, agile development, and a user-centric design philosophy.

• The company values innovation and efficiency, as reflected in its product and the description of its work environment.

• Design systems and brand consistency are key operational methodologies, ensuring a unified and scalable user experience.

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

📝 Enhancement Note: Understanding Smartsheet's SaaS context and its focus on work management provides insight into the potential demands on the design team. The company's scale suggests a need for robust, scalable design solutions and strong brand governance.

📈 Career & Growth Analysis

Operations Career Level: This role is a senior individual contributor position, specifically a "Lead" role within Visual Design. It signifies a high level of expertise, strategic influence, and mentorship responsibilities. It's a step above a standard Visual Designer, requiring leadership in conceptualization, system design, and project execution.

Reporting Structure: The Lead Visual Designer reports to the Creative Director in Costa Rica. This structure implies a clear hierarchy within the Brand Studio, with opportunities for direct mentorship and guidance from a senior creative leader.

Operations Impact: As a Lead Visual Designer, the impact is significant. You will directly influence how Smartsheet's brand is perceived globally, impacting marketing effectiveness, user engagement with the product, and overall brand equity. Your work in design systems will also drive efficiency and consistency across the organization.

Growth Opportunities:

• Leadership Advancement: Potential to grow into a Creative Director role or manage a larger design team as the company and its creative operations expand.

• Specialization: Deepen expertise in specific areas like motion graphics, AI-driven design, or advanced brand system architecture.

• Cross-Functional Influence: Expand influence into product design strategy or lead larger, more complex brand initiatives.

• Skill Development: Leverage provided learning resources (LinkedIn Learning) to stay at the forefront of design trends, tools, and methodologies.

📝 Enhancement Note: The "Lead" title suggests a path towards more formal management or a highly specialized senior contributor track. The company's size and industry offer ample opportunities for growth and impact in a dynamic environment.

🌐 Work Environment

Office Type: The role is fully remote within Costa Rica. This means the primary work environment is a home office, with the expectation of high self-discipline and effective remote collaboration tools.

Office Location(s): While remote, the role is based in Costa Rica, likely aligning with a specific timezone (America/Costa Rica). Smartsheet may have physical offices in other locations, but this role operates without an assigned physical workspace.

Workspace Context:

• Remote Collaboration: Expect a heavy reliance on digital collaboration tools (e.g., Slack, Google Workspace, Smartsheet itself, Figma, Zeplin) for communication, file sharing, and real-time feedback.

• Technology & Tools: Access to industry-standard design software (Adobe Creative Suite) is essential, with potential for company-provided licenses or stipends to acquire necessary tools.

• Team Interaction: While remote, opportunities for virtual team meetings, design critiques, and one-on-one sessions with the Creative Director and peers will be crucial for collaboration and professional development.

Work Schedule:

• The standard working hours are approximately 40 per week, typical for a full-time, senior-level position. Flexibility is implied by the remote nature, but core hours for team collaboration and availability for key meetings will be necessary.

📝 Enhancement Note: The remote-first nature within a specific country requires strong self-management skills and proficiency in digital collaboration tools. The emphasis is on asynchronous and synchronous communication to maintain team cohesion and project momentum.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by a recruiter to assess basic qualifications and alignment with the role's requirements.

• Portfolio Presentation & Interview: A session where you will present your portfolio to the hiring team (likely including the Creative Director and potentially other designers). Be prepared to discuss your process, strategic thinking, and specific project outcomes.

• Skills/Technical Interview: This might involve a design exercise or a deep dive into your technical skills, system thinking, and problem-solving approach.

• Cross-Functional/Stakeholder Interview: An interview with key stakeholders from marketing, product, or other departments to assess collaboration skills and understanding of business needs.

• Final Interview: Potentially with senior leadership to discuss overall fit, strategic vision, and leadership potential.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest, most relevant projects that showcase your ability to drive brand evolution, manage design systems, and lead complex visual design initiatives.

• Tell a Story: For each project, clearly articulate the challenge, your strategic approach, your design process, the tools and techniques used, and most importantly, the measurable impact or business outcome. Use the STAR method (Situation, Task, Action, Result).

• Highlight Leadership: For a Lead role, ensure your portfolio demonstrates instances where you mentored others, managed project timelines, or influenced strategic decisions.

• Showcase Systems Thinking: If you have experience with design systems, clearly explain their architecture, how you contributed, and how they improved efficiency or consistency.

• Be Ready for Questions: Anticipate questions about your creative process, how you handle feedback, your approach to collaboration, and your understanding of current design trends (including AI).

Challenge Preparation:

• Design Exercise: Be prepared for a potential design challenge, which could involve critiquing existing work, proposing solutions to a given problem, or creating a small concept based on a prompt. Focus on demonstrating your process and strategic thinking, not just the final output.

• Case Study Deep Dive: Be ready to walk through a case study from your portfolio in detail, explaining the 'why' behind your decisions and the impact of your work.

• Stakeholder Empathy: Practice articulating how you would approach understanding and meeting the needs of different stakeholders across marketing and product.

📝 Enhancement Note: The interview process is designed to assess not just design talent but also leadership, strategic thinking, and collaborative capabilities. A well-prepared portfolio presentation is critical for success.

🛠 Tools & Technology Stack

Primary Tools:

• Adobe Creative Suite: Essential mastery of Illustrator, Photoshop, InDesign, Creative Cloud, Firefly, and Express for core visual design tasks.

• Figma: Highly preferred for UI/UX design, prototyping, and collaborative design system work.

• Zeplin: Beneficial for design handoff to development teams.

Analytics & Reporting:

• Familiarity with web analytics tools (e.g., Google Analytics) to understand user behavior and inform design decisions.

CRM & Automation:

• While not a direct CRM/automation role, understanding how design impacts user journeys within CRM and marketing automation platforms is advantageous.

Other Potential Tools:

• Motion Graphics: After Effects for animated elements and video content.

• Webflow: For website design and prototyping.

• HTML/CSS: Basic understanding to facilitate better collaboration with web developers.

• Drupal: Experience with CMS platforms if involved in web content design.

📝 Enhancement Note: Proficiency in Adobe Creative Suite is a must. Figma is increasingly standard for collaborative design and system work. Familiarity with AI design tools is also noted as a valuable addition. Understanding Smartsheet's own platform is key for this internal role.

👥 Team Culture & Values

Operations Values:

• Impact-Driven: A focus on creating work that has a tangible impact on the business, brand perception, and user experience.

• Collaboration: Valuing teamwork, open communication, and acting as a peer to stakeholders across departments.

• Excellence & Craftsmanship: A commitment to high-quality design execution and continuous improvement of skills.

• Innovation: Encouraging new ideas, exploring emerging technologies (like AI), and pushing creative boundaries.

• Ownership & Accountability: Taking responsibility for projects from start to finish and proactively addressing challenges.

Collaboration Style:

• Partnership: Working as a true partner with stakeholders, understanding their goals, and co-creating solutions.

• Constructive Feedback: A culture where feedback is given and received openly and constructively to improve design outcomes.

• Systemic Thinking: Approaching design challenges with an understanding of how individual pieces fit into larger systems and brand frameworks.

• Global Awareness: Designing with an understanding of diverse cultural contexts and international market needs.

📝 Enhancement Note: Smartsheet emphasizes a culture of achieving significant outcomes through collaboration, innovation, and a strong sense of ownership, all while maintaining high standards of design quality.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Brand Evolution with System Consistency: Navigating the need to push creative boundaries while ensuring all work adheres to established brand guidelines and design systems.

• Remote Collaboration Dynamics: Effectively collaborating and maintaining strong relationships with a distributed team and stakeholders without in-person interaction.

• Prioritization Across Multiple Projects: Managing a demanding workload with competing deadlines and stakeholder needs, requiring excellent time management and prioritization skills.

• Integrating Emerging Technologies: Staying current with and effectively incorporating new technologies like Generative AI into the design workflow and brand expression.

Learning & Development Opportunities:

• Advanced Design System Development: Opportunity to deepen expertise in building and scaling sophisticated design systems.

• AI in Design: Explore and implement cutting-edge AI tools and methodologies in visual design and brand strategy.

• Mentorship and Leadership: Develop leadership skills through guiding junior designers and contributing to strategic creative direction.

• Industry Exposure: Access to professional development resources like LinkedIn Learning and potential for industry event participation.

📝 Enhancement Note: The role presents opportunities to tackle complex design challenges at scale, leverage new technologies, and grow into a leadership position within a respected SaaS company.

💡 Interview Preparation

Strategy Questions:

• "How would you approach evolving the Smartsheet brand identity while maintaining consistency across all touchpoints?" (Prepare to discuss brand strategy, system thinking, and phased rollout plans.)

• "Describe a time you had to influence stakeholders who had different visions for a design project. What was your approach?" (Focus on communication, negotiation, and data-driven persuasion.)

• "Walk us through the process of creating or contributing to a design system. What were the key challenges and how did you overcome them?" (Detail your methodology, collaboration, and documentation approach.)

Company & Culture Questions:

• "What interests you most about Smartsheet and our mission?" (Research Smartsheet's product, values, and recent news.)

• "How do you foster collaboration within a remote team and with cross-functional partners?" (Provide specific examples of your communication and teamwork strategies.)

Portfolio Presentation Strategy:

• Structure is Key: Organize your presentation logically, starting with an overview, then diving into 2-3 in-depth case studies.

• Focus on the 'Why' and 'How': Don't just show pretty pictures. Explain the strategic thinking behind your design decisions and the process you followed.

• Quantify Impact: Where possible, present metrics or evidence of how your designs achieved business goals (e.g., increased engagement, improved conversion rates, brand perception shifts).

• Be Enthusiastic and Authentic: Let your passion for design and problem-solving shine through.

📝 Enhancement Note: Preparation should focus on demonstrating strategic thinking, leadership potential, and a deep understanding of design systems and brand building, tailored to Smartsheet's context.

📌 Application Steps

To apply for this Lead Visual Designer position:

• Submit your application through the Smartsheet careers portal at https://job-boards.greenhouse.io/smartsheet/jobs/7736367.

• Portfolio Customization: Tailor your portfolio to highlight projects demonstrating brand evolution, design system expertise, and leadership. Ensure it clearly showcases your process and impact.

• Resume Optimization: Update your resume to emphasize your 10+ years of experience, specific achievements in visual design leadership, and proficiency with required tools (Adobe Creative Suite, Figma). Use keywords from the job description.

• Interview Preparation: Practice articulating your design philosophy, process, and how you approach strategic challenges. Prepare to present your portfolio with confidence and engage in thoughtful discussions about your work.

• Company Research: Gain a deep understanding of Smartsheet's product, target audience, brand voice, and recent marketing efforts. Familiarize yourself with their existing design systems and brand guidelines.

⚠️ 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.

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