Senior Product Designer II (Remote Eligible)

📍 Job Overview

Job Title: Senior Product Designer II (Remote Eligible)

Company: Smartsheet

Location: United States (Remote)

Job Type: Full-Time

Category: Product Design / User Experience

Date Posted: 2026-09-10

Experience Level: Mid-Senior Level (7+ years)

Remote Status: Fully Remote

🚀 Role Summary

• Drive the conceptualization and creation of elegant, scalable user experiences for Smartsheet's enterprise-grade work execution platform, impacting both web and mobile applications.

• Champion human-centered design methodologies, user research, and data-driven insights to inform product strategy and ensure solutions meet complex enterprise user needs.

• Lead the design of sophisticated platform architecture and features, contributing to the maturity of design systems and elevating design quality across the organization.

• Foster cross-functional collaboration with product management, engineering, and research teams to align on strategy, execution, and deliver measurable business outcomes.

• Mentor junior designers, share best practices, and contribute to a culture of design excellence and continuous learning within the Experience Design team.

📝 Enhancement Note: This role is specifically focused on enterprise and platform design, demanding a strategic approach to complex workflows, scalability, and sophisticated user needs within a B2B SaaS context. The emphasis on "agentic and generative design workflows" indicates a forward-thinking approach to incorporating AI into the design process.

📈 Primary Responsibilities

• Conceptualize, design, and iterate on intuitive and engaging user experiences for Smartsheet's web and mobile applications, with a focus on enterprise and platform-level features.

• Translate complex user needs, business goals, and technical constraints into elegant, scalable design solutions that enhance platform architecture and feature depth.

• Lead design thinking workshops and facilitate cross-functional alignment sessions to define project goals, gather requirements, and ensure cohesive product strategy.

• Advocate for user needs and represent the end-user perspective throughout the product development lifecycle, leveraging user research, data analytics, and usability testing.

• Contribute to and leverage Smartsheet's design systems, component libraries, and design infrastructure to ensure consistency, scalability, and efficiency in design delivery.

• Collaborate closely with product managers, engineers, researchers, and other stakeholders to define product roadmaps, align on execution plans, and ensure successful feature launches.

• Mentor and guide junior designers, providing feedback, sharing expertise in design craft, and fostering their professional development to elevate the team's overall capabilities.

• Champion accessibility standards (WCAG) and ensure all designs are inclusive and meet the needs of a diverse user base.

• Drive understanding and alignment across product teams regarding new feature development and the evolution of existing functionalities.

• Contribute to the continuous improvement of design processes, tools, and methodologies within the Experience Design team.

📝 Enhancement Note: The responsibilities highlight a blend of individual design craft and leadership. The emphasis on "driving strategic impact by designing scalable, sophisticated experiences" and "elevating our platform architecture and feature depth" suggests a role that influences the long-term vision and technical foundation of the product, not just feature-level UI.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design (Interaction, Product, Communication, HCD, or related) or equivalent professional experience.

Experience: 7+ years of experience as a Product Designer, Interaction Designer, or similar role, with a strong track record in SaaS or enterprise environments.

Required Skills:

• Design Thinking & User Advocacy: Proven ability to apply design thinking principles and advocate for user needs through research, empathy, and data.

• Enterprise & SaaS Design Expertise: Demonstrated experience delivering complex, scalable, and sophisticated user experiences within B2B SaaS or enterprise software platforms.

• Visual & Interaction Design Craft: Strong visual design skills coupled with a deep understanding of interaction design principles, hierarchy, typography, color, and layout.

• Design Systems Proficiency: Applied understanding and experience with design systems, component libraries, and design infrastructure to ensure consistency and scalability.

• Collaboration & Influence: Excellent collaboration skills, with the ability to effectively partner with product, engineering, and research teams, and resilience in managing stakeholder feedback.

• Workshop Facilitation: Experience facilitating design activities and design thinking workshops to align teams on goals, outcomes, and requirements.

• Accessibility Standards: Applied understanding of accessibility (WCAG) standards and commitment to designing inclusive experiences.

• Modern Design Methodologies: Expertise in agentic and generative design workflows, leveraging modern tools and methodologies to accelerate design exploration and validation.

• Communication & Storytelling: Ability to clearly explain and defend design ideas, solutions, and their merits across various mediums to diverse audiences.

• Leadership & Mentorship: Demonstrated leadership qualities through design work, mentoring junior team members, and influencing design quality at an organizational level.

Preferred Skills:

• Experience with user research, usability testing, or user-centered design validation methodologies.

• Familiarity with AI-assisted design tools and practices, or experience integrating generative workflows into existing design processes.

• Experience designing for advanced B2B SaaS/Enterprise products with complex workflows.

• Experience with design systems, component libraries, or design infrastructure development.

📝 Enhancement Note: The requirement for 7+ years of experience, coupled with leadership and organizational influence, positions this as a senior individual contributor role with significant impact. The explicit mention of "agentic and generative design workflows" and "platform architecture" signifies a need for forward-thinking designers comfortable with emerging technologies and system-level design.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase a minimum of 2-3 complex enterprise-level design projects that demonstrate your ability to solve sophisticated user problems within a SaaS or platform context.

• Include case studies that detail your design process, from initial problem definition and user research through to final solution and impact.

• Highlight specific examples of how you have contributed to or leveraged design systems, component libraries, or design infrastructure.

• Clearly articulate the business objectives and user needs addressed by each project, and quantitatively demonstrate the impact of your design solutions (e.g., user adoption, efficiency gains, conversion rates). Process Documentation:

• Provide detailed explanations of your design process, emphasizing your approach to design thinking, user research, ideation, prototyping, and validation.

• Illustrate your methods for collaborating with cross-functional teams (Product, Engineering, Research) and managing stakeholder feedback throughout the design lifecycle.

• Demonstrate your understanding of how to design for scalability, maintainability, and accessibility within a product ecosystem.

• Showcase your experience with modern design tools and methodologies, particularly those related to generative design, AI-assisted workflows, and design system management.

📝 Enhancement Note: Given the role's focus on enterprise and platform design, portfolios should heavily emphasize scalability, system-level thinking, and the ability to influence design quality across an organization. Case studies demonstrating complex problem-solving and measurable business outcomes are crucial.

💵 Compensation & Benefits

Salary Range: $155,000 - $220,000 USD per year. This range reflects the company's assessment of the role's market value, considering factors such as experience level, skills, and candidate location within the US. It is important to note that the final compensation may vary based on individual qualifications and the specific hiring location.

Benefits:

• Health & Wellness: Employer-subsidized medical, vision, and dental coverage for full-time employees.

• Financial Security: 401k match (50% of your contribution up to the first 6% of eligible pay) to support retirement savings.

• Productivity Support: Monthly stipend to enhance your work environment and productivity.

• Work-Life Balance: Flexible Time Away Program and Sick Time Off, encouraging a healthy balance.

• Comprehensive Insurance: Company-sponsored life insurance, short-term, and long-term disability plans for all US employees.

• Paid Time Off: 12 paid holidays per year.

• Family Support: Up to 24 weeks of Parental Leave.

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

• Professional Development: Access to Udemy online courses and opportunities for continuous learning and growth.

• Additional Perks: Counseling membership, local retail discounts, and a personal Smartsheet account.

Working Hours: Standard 40 hours per week, with flexibility offered to accommodate remote work arrangements and individual productivity needs.

📝 Enhancement Note: The salary range is competitive for a Senior Product Designer II role in the US market, especially for a remote position with a company like Smartsheet. The benefits package is comprehensive, emphasizing employee well-being, financial security, and professional development, which are attractive to experienced professionals. The mention of "Teleworking options from any registered location in the U.S. (role specific)" confirms the remote nature.

🎯 Team & Company Context

🏢 Company Culture

Industry: Software / Work Execution Platform

Company Size: Smartsheet is a well-established company with a significant presence, indicated by its "category-leading" status and broad employee base. This suggests a structured environment with opportunities for impact within a large organization.

Founded: Over 20 years ago, indicating a mature and stable company with a proven track record in the market.

Team Structure:

• The Experience Design team operates within a larger product and engineering organization, reporting to a Manager, Product Design.

• This role involves close partnership with research and data teams, as well as product management and engineering counterparts.

• The structure supports cross-functional collaboration, with opportunities for mentorship and leadership within the design discipline. Methodology:

• Human-Centered Design: Strong emphasis on understanding and advocating for end-user needs through design thinking and research.

• Data-Driven Decisions: Collaboration with research and data teams to inform and validate design solutions.

• Scalable Systems: Focus on designing robust, scalable experiences and contributing to design infrastructure, including design systems.

• AI Integration: Forward-thinking approach, actively exploring and integrating agentic and generative design workflows.

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

📝 Enhancement Note: Smartsheet's culture appears to value innovation, collaboration, and employee growth, as evidenced by their mission to unite human teams with AI and their comprehensive benefits. The emphasis on "magic at work" suggests a drive for impactful and engaging solutions.

📈 Career & Growth Analysis

Operations Career Level: Senior Product Designer II. This level signifies a highly experienced individual contributor who not only executes design tasks at a high level but also influences design strategy, mentors others, and contributes to the maturity of design systems and processes.

Reporting Structure: Reports to the Manager, Product Design. This indicates a clear line of management and potential for guidance and career development conversations.

Operations Impact: This role has a significant impact on the product's usability, elegance, and value proposition, particularly for enterprise clients. By designing scalable and sophisticated experiences, the designer directly contributes to Smartsheet's ability to empower large organizations and drive measurable business outcomes, thus influencing revenue and customer success.

Growth Opportunities:

• Design Leadership: Opportunities to grow into lead designer roles, taking ownership of larger product areas or strategic initiatives, and further developing mentorship capabilities.

• Specialization: Potential to deepen expertise in specific areas such as platform architecture, AI-driven design, accessibility, or user research methodologies.

• Strategic Influence: Increased involvement in product strategy, roadmap planning, and defining the future direction of the Smartsheet platform.

• Cross-functional Advancement: Development of skills in stakeholder management and strategic communication that can lead to broader influence within the company.

📝 Enhancement Note: The "Senior II" title suggests a step beyond a standard senior role, implying a higher level of autonomy, strategic contribution, and potential for mentorship or technical leadership. Growth opportunities are likely tied to expanding influence, deepening expertise, and potentially moving into team lead or principal designer roles.

🌐 Work Environment

Office Type: This role is designated as "Remote Eligible" and can be worked from "anywhere in the US where Smartsheet is a registered employer." This indicates a fully remote work environment, prioritizing flexibility and work-life balance.

Office Location(s): While the role is remote, Smartsheet is a registered employer in various US locations, suggesting a distributed workforce.

Workspace Context:

• Digital Collaboration: The remote nature necessitates strong reliance on digital collaboration tools for communication, design reviews, and project management.

• Ergonomics & Productivity: The monthly stipend suggests an expectation that employees will invest in creating an optimal home office setup conducive to productive design work.

• Team Interaction: While remote, there will be structured opportunities for team interaction through virtual meetings, design critiques, and collaborative design sessions.

Work Schedule: A standard 40-hour work week is expected, with flexibility inherent in a remote role to manage personal schedules around core collaboration times. This allows for focused deep work periods crucial for complex design tasks.

📝 Enhancement Note: The emphasis on a remote-first approach means the candidate must be self-disciplined, highly communicative, and proficient with remote collaboration tools. The monthly stipend is a practical benefit for setting up a productive home workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter or hiring manager will review applications and portfolios to assess basic qualifications and alignment with the role's requirements.

• Portfolio Review & Design Challenge: Candidates will likely present their portfolio, discussing their process, strategic thinking, and impact on specific projects. A design challenge, potentially focused on a complex enterprise scenario or platform-level problem, may be assigned to evaluate design thinking, problem-solving skills, and execution.

• Cross-functional Interviews: Interviews with Product Managers, Engineering leads, and fellow Designers to assess collaboration skills, technical understanding, and cultural fit.

• Hiring Manager Interview: A final interview with the Hiring Manager to discuss overall fit, career aspirations, and deeper insights into the role and team.

Portfolio Review Tips:

• Highlight Enterprise & Platform: Focus on projects that demonstrate your ability to handle complex workflows, scalable solutions, and enterprise-level requirements.

• Showcase Process & Strategy: Clearly articulate your design process, decision-making rationale, and how you aligned with business and user goals. Use diagrams, wireframes, and user flows to illustrate your thinking.

• Quantify Impact: Wherever possible, present metrics and data that demonstrate the success and ROI of your design contributions.

• AI & System Design: Explicitly call out any experience with generative design, AI-assisted tools, or contributions to design systems/platform architecture.

• Storytelling: Structure your case studies as compelling narratives that showcase your problem-solving skills and impact.

Challenge Preparation:

• Understand Smartsheet's Context: Research Smartsheet's product, target audience (enterprise users), and competitive landscape.

• Focus on Scalability & Sophistication: Anticipate challenges that require designing for complex, multi-user scenarios and large-scale data management.

• Demonstrate Design Thinking: Be prepared to walk through your problem-solving approach, from understanding the problem to ideating and iterating on solutions.

• Articulate Trade-offs: Be ready to discuss design trade-offs, constraints, and how you would prioritize solutions in a real-world scenario.

📝 Enhancement Note: The interview process is likely rigorous, emphasizing not just design execution but also strategic thinking, collaboration, and the ability to handle complex enterprise challenges. A well-curated portfolio that directly addresses the role's specific requirements (enterprise, platform, AI, design systems) will be paramount.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable given industry standards for collaborative design), Sketch, Adobe Creative Suite (Photoshop, Illustrator).

• Design Systems: Experience with creating, maintaining, or contributing to established design systems and component libraries.

• Collaboration & Communication: Slack, Microsoft Teams, Zoom, Google Workspace.

• Project Management: Jira, Asana, or similar tools for tracking tasks and project progress.

Analytics & Reporting:

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

• Ability to interpret data and user research findings to drive design iterations. CRM & Automation:

• While not a direct CRM role, understanding how design impacts user journeys within a CRM context could be beneficial.

• Familiarity with how design interfaces with automated workflows and business processes.

📝 Enhancement Note: Proficiency with industry-standard design tools like Figma is a given. The role's emphasis on design systems and enterprise SaaS suggests a need for designers who can work with structured design libraries and understand how their designs integrate into larger product platforms and workflows. Experience with AI-assisted design tools is a plus.

👥 Team Culture & Values

Operations Values:

• User-Centricity: A deep commitment to understanding and serving the needs of enterprise users, ensuring the platform is valuable, elegant, and engaging.

• Collaboration & Partnership: Strong emphasis on working cross-functionally with product, engineering, and research to achieve shared goals and drive collective success.

• Quality & Craftsmanship: A commitment to maintaining a high standard of design quality, from visual aesthetics to interaction design and accessibility.

• Innovation & Future-Forward Thinking: Embracing new methodologies like agentic and generative design, and a desire to explore and evolve design practices.

• Impact & Outcomes: A focus on delivering measurable business outcomes and empowering teams through effective work execution.

Collaboration Style:

• Transparent & Iterative: Encourages open communication, feedback exchange, and iterative design processes to refine solutions.

• Cross-Functional Integration: Works closely with diverse teams, fostering a shared understanding of product goals and user needs.

• Mentorship & Knowledge Sharing: A culture that supports the growth of team members through guidance, shared learning, and best practice dissemination.

📝 Enhancement Note: The team culture at Smartsheet seems to foster a blend of user advocacy, collaborative problem-solving, and a forward-looking approach to design, particularly with the integration of AI. The emphasis on "magic at work" suggests a drive for creating truly impactful and enjoyable user experiences.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Scale & Complexity: Addressing the intricate needs of enterprise users and designing for highly scalable platform features within a sophisticated SaaS product.

• Balancing Innovation with Stability: Integrating new technologies like AI-driven design while maintaining the reliability and usability of a mature enterprise platform.

• Cross-Functional Alignment: Navigating diverse stakeholder perspectives and technical constraints to achieve cohesive and effective design solutions.

• Evolving Design Methodologies: Staying current with emerging design trends, tools (e.g., AI-assisted design), and user expectations in a rapidly changing tech landscape.

Learning & Development Opportunities:

• Deepening Platform Design Expertise: Gaining in-depth knowledge of enterprise software architecture and complex user workflows.

• Mastering AI in Design: Exploring and implementing AI-assisted design tools and generative workflows to enhance efficiency and creativity.

• Leadership Development: Opportunities to mentor junior designers, lead design initiatives, and contribute to strategic product decisions.

• Industry Exposure: Potential to attend relevant design conferences or workshops to stay abreast of industry best practices and emerging trends.

📝 Enhancement Note: The primary challenges revolve around the inherent complexity of enterprise software design and the integration of cutting-edge technologies. Growth opportunities are strongly aligned with developing expertise in these areas and moving into more influential design leadership roles.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you designed a complex enterprise feature. What were the key challenges, how did you approach them, and what was the outcome?" (Focus on process, problem-solving, and impact.)

• "How do you approach designing for scalability and maintaining consistency within a large product ecosystem or design system?" (Assess system-level thinking and design system proficiency.)

• "Discuss your experience with agentic or generative design tools. How have you leveraged them, or how would you integrate them into a product design workflow?" (Gauge familiarity with AI in design and forward-thinking approach.)

• "How do you balance user needs with business objectives and technical constraints when designing a new feature?" (Evaluate strategic thinking and trade-off management.) Company & Culture Questions:

• "What excites you about Smartsheet's mission and its approach to the future of work, particularly with AI integration?" (Assess alignment with company vision and interest.)

• "How do you foster collaboration with product managers and engineers, especially in a remote environment?" (Understand collaboration style and remote work effectiveness.)

• "Describe your experience mentoring junior designers. What is your philosophy on elevating design craft within a team?" (Evaluate leadership and mentorship capabilities.) Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role, your process, the solution, and the measurable results.

• Emphasize Enterprise Context: Highlight the specific challenges of designing for enterprise users, complex workflows, and scalable solutions.

• Showcase Design Systems & AI: If applicable, dedicate time to explaining your contributions to design systems or your use of AI-assisted design tools.

• Be Ready for Deep Dives: Anticipate detailed questions about your design decisions, trade-offs, and the rationale behind your choices.

• Quantify Your Impact: Use data and metrics to demonstrate the success and value of your design work.

📝 Enhancement Note: Interview preparation should heavily lean into demonstrating strategic thinking, enterprise design expertise, and comfort with modern design methodologies, including AI. The portfolio presentation is a critical component, requiring a clear and compelling narrative of impactful design work.

📌 Application Steps

To apply for this Senior Product Designer II position:

• Submit your application through the Smartsheet careers portal at https://job-boards.greenhouse.io/smartsheet/jobs/8191836.

• Curate Your Portfolio: Select 2-3 of your most impactful enterprise-level design projects that showcase your process, strategic thinking, and quantifiable results. Ensure these projects highlight your ability to design for scalability, complex workflows, and ideally, demonstrate experience with design systems or AI-assisted design.

• Tailor Your Resume: Update your resume to clearly articulate your 7+ years of experience, focusing on achievements in SaaS/enterprise design, design leadership, and proficiency with relevant tools and methodologies. Use keywords from the job description, such as "enterprise design," "platform architecture," "design systems," and "generative design."

• Prepare Your Narrative: Practice presenting your portfolio case studies, focusing on storytelling, articulating your design decisions, and quantifying the impact of your work. Be ready to discuss your approach to collaboration and mentorship.

• Research Smartsheet: Familiarize yourself with Smartsheet's product, company mission, and their vision for the future of work, especially regarding AI integration. Understand their target audience and competitive positioning to tailor your responses and demonstrate genuine interest.

⚠️ 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.