Staff Product Designer

📍 Job Overview

Job Title: Staff Product Designer

Company: Scale to Win, Inc

Location: Santa Ana, California, United States

Job Type: FULL_TIME

Category: Product Design / GTM Operations Enablement

Date Posted: 2026-05-12

Experience Level: 10+ Years

Remote Status: Fully Remote

🚀 Role Summary

• Lead end-to-end product design and architect the UX vision for high-impact product initiatives, functioning as a strategic partner to Product and Engineering leadership.

• Translate highly complex customer problems into elegant, scalable, and technically sound solutions by leveraging systems thinking and balancing near-term delivery with long-term experience quality.

• Champion the customer voice and user experience through rigorous research, usability testing, and data-driven insights, advocating for simplicity, clarity, and accessibility in all design outputs.

• Drive the evolution of product design craft at Scale to Win by establishing design philosophy, standardizing user experience best practices, and integrating AI across all product squads.

📝 Enhancement Note: While the title is "Staff Product Designer", the responsibilities and experience requirements indicate a senior, strategic role focused on shaping entire product pillars and design systems, which has significant implications for Go-to-Market (GTM) operations enablement. This role will influence how Sales, Marketing, and Customer Success teams interact with and leverage the product.

📈 Primary Responsibilities

• Own the complete product design lifecycle, from discovery and user experience design to visual design, prototyping, and final delivery for key product areas on the roadmap.

• Develop sophisticated workflows and systems that adeptly balance user usability, scalability, and technical constraints, ensuring robust and resilient product ecosystems for 2-3 year horizons.

• Conduct and lead customer research, usability testing, and validation activities, utilizing qualitative and quantitative insights to rigorously inform and validate design decisions.

• Partner closely with Product and Engineering leadership to collaboratively architect the overarching product vision and introduce innovative tools and methodologies for design discussions and workshops.

• Engage with Customer Success, Sales, and other GTM stakeholders to ensure user insights and client feedback are effectively incorporated into product design strategies, directly impacting user adoption and client satisfaction.

• Contribute to defining and elevating company-wide standards for product design excellence, modeling strong design and systems thinking for the broader team and providing thoughtful critique to enhance overall initiative quality.

• Collaborate with the existing design team to establish the distinct 'Scale to Win' design philosophy, standardizing approaches to user experience, user-centricity, accessibility, and AI integration across all product squads.

📝 Enhancement Note: The emphasis on "systems thinking," "scalability," and "long-term product ecosystem" suggests a need for a designer who can not only create individual features but also ensure the entire product suite is cohesive and supports future growth, which is critical for GTM scalability. The mention of "Customer Success, Sales, and other stakeholders" directly links this design role to GTM operations.

🎓 Skills & Qualifications

Education: While no specific degree is listed, a Bachelor's or Master's degree in Design, HCI, Computer Science, or a related field is typically expected for senior-level roles of this nature. A strong portfolio can often substitute for formal education.

Experience: 10+ years of progressive experience in product design, with a demonstrated track record of leading design for complex problem areas and entire product verticals, particularly within B2B SaaS environments.

Required Skills:

• End-to-End Product Design: Proven ability to manage the entire design process from discovery to delivery for complex product areas.

• Systems Thinking: Expertise in designing scalable, cohesive product ecosystems that anticipate future shifts and technical constraints.

• User Experience (UX) Design: Deep understanding of user-centered design principles, information architecture, and interaction design for B2B SaaS applications.

• Visual Design & Prototyping: Proficiency in creating high-fidelity mockups, interactive prototypes, and establishing visual design languages.

• Customer Research & Validation: Experience in planning and executing user research, usability testing, and synthesizing insights to drive design decisions.

• Design Systems: Experience building, contributing to, and maintaining robust design systems to ensure consistency and scalability across products.

• Product Strategy & Prioritization: Strong product thinking capabilities, with the ability to use business, customer, and technical context to inform trade-offs and prioritize design efforts.

• Cross-functional Collaboration: Demonstrated ability to partner effectively with Product Management, Engineering, Customer Success, and Sales teams.

• Influence & Leadership: Proven experience leading through influence, winning buy-in for bold design directions, and mentoring junior designers.

• Accessibility Advocacy: Commitment to and experience designing for accessibility standards to ensure inclusive user experiences.

Preferred Skills:

• Experience designing data visualization tools and dashboards for analytics and reporting.

• Familiarity with fundraising, organizing, or political campaign technology products.

• Experience designing messaging platforms (e.g., texting tools) and communication workflows.

• Experience in political organizing or campaign work, providing domain context.

• Experience leveraging AI-powered tools to accelerate product development workflows and enhance user experiences.

📝 Enhancement Note: The "10+ years of experience" and the emphasis on "leading design for complex problem areas and entire product verticals" combined with "systems thinking" and "design systems" strongly suggest a need for an operations-minded designer who can build scalable frameworks that support GTM functions. The preferred skills in data visualization and messaging tools are highly relevant to campaign operations and client communication.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase at least 2-3 comprehensive case studies demonstrating end-to-end product design ownership for complex B2B SaaS problems or entire product verticals.

• Highlight examples of systems thinking, illustrating how you designed for scalability, long-term product ecosystem resilience, and technical constraints.

• Include projects where you navigated significant technical or business ambiguity, detailing your problem-solving process and strategic decision-making.

• Present your experience building or contributing to design systems, emphasizing their impact on consistency, efficiency, and scalability.

Process Documentation:

• Detail your approach to user research and validation, including methodologies used, participant recruitment strategies, and how findings influenced design iterations.

• Illustrate your process for translating complex customer problems into elegant, user-centered solutions, showing the evolution from initial concepts to final designs.

• Provide examples of how you balanced near-term delivery needs with long-term experience quality and technical feasibility in your design process.

• Showcase your collaboration process with Product, Engineering, and GTM stakeholders, highlighting how you incorporated feedback and managed differing priorities.

📝 Enhancement Note: For a role of this seniority and focus on "systems thinking" and "product verticals," the portfolio is paramount. It should not only display visual and UX skills but also strategic thinking, process documentation, and the ability to design for complex operational workflows that underpin GTM activities. The emphasis on "navigating significant technical or business ambiguity" is a key indicator of the need for robust process demonstration.

💵 Compensation & Benefits

Salary Range: $220,000 yearly salary (base). Salaries are non-negotiable as part of the company's commitment to equity.

Benefits:

• Financial:

  • $220,000 base salary.
  • Potential for discretionary bonus.
  • 401k matching up to 6% after a provisional period.

• Time Off:

  • Ten paid company holidays.
  • Two floating holidays.
  • A week and a half-long holiday break at the end of the year.
  • Generous paid vacation (up to 24 days per year, accrued monthly).
  • Paid sick leave.
  • Paid short-term medical, caregiver, bereavement, and other personal leave.

• Family & Health:

  • 16 weeks of paid parental leave.
  • Additional 4 weeks of part-time, fully-paid flex time for new parents.
  • Fully-paid premium, $0 deductible, top-notch medical insurance for employee and dependents.
  • Comprehensive dental and vision insurance for employee and dependents.

• Work & Development:

  • Fully remote working environment with flexible conditions.

  • Stipend to support home office setup.

  • Company-provided computer.

  • Annual $2,000.00 stipend for professional development goals.

  • Opportunity to donate 25,000 free texts annually to a non-profit of choice. Working Hours: Based on the "40" value derived from the input, it's assumed to be a standard 40-hour work week. The role emphasizes remote working with flexible conditions, allowing for adaptability in daily schedules as long as responsibilities are met and collaboration with teams across different time zones is managed effectively.

📝 Enhancement Note: The salary of $220,000 is at the higher end for a Staff Product Designer, reflecting the seniority, strategic impact, and the company's focus on political tech where rapid iteration and effective GTM tools are crucial. The comprehensive benefits package, especially the generous parental leave, home office stipend, and professional development budget, are attractive for senior remote professionals. The unique benefit of donating texts to a non-profit aligns with the company's mission.

🎯 Team & Company Context

🏢 Company Culture

Industry: Political Technology (Political Tech) / SaaS. Scale to Win operates at the intersection of technology and progressive politics, providing essential digital tools for campaigns and organizations to drive change and mobilize voters. This niche requires a deep understanding of fast-paced, high-stakes environments.

Company Size: The input does not specify exact employee count, but the description mentions working with over 3,000 clients and having founders from major presidential campaigns, suggesting a growing company with a significant market presence and impact.

Founded: 2020. This indicates a relatively young, agile, and innovative company built by experienced organizing leaders.

Team Structure:

• The Product Design team is likely small and evolving, typical for an early-stage B2B SaaS company. As a Staff Designer, you will be a senior leader within this team, potentially shaping its future direction.

• This role involves significant cross-functional partnership with Product Management and Engineering leadership, implying a collaborative, matrixed structure where influence is key.

Methodology:

• Data-Driven Design: The role emphasizes using qualitative and quantitative insights from customer research, usability testing, and client feedback to inform design decisions. This aligns with a data-driven approach to product development.

• Systems & Scalability Focus: The requirement for "systems thinking" and designing for "scalability" and the "long-term product ecosystem" points to a methodical approach to building robust, maintainable, and future-proof products.

• Agile & Iterative Development: Given the political tech context and early-stage company, an agile and iterative design and development process is likely in place, balancing rapid delivery with strategic long-term vision.

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

📝 Enhancement Note: The company's mission-driven nature in the political tech space implies a fast-paced, impact-oriented culture. The "fully-remote" setup necessitates strong asynchronous communication skills and a proactive approach to collaboration. The emphasis on "organizing leaders" suggests a culture that values strategic thinking, grassroots engagement, and effective communication.

📈 Career & Growth Analysis

Operations Career Level: Staff Product Designer. This is a senior individual contributor role, often considered a career-level position that doesn't necessarily imply management but signifies deep expertise, strategic influence, and the ability to lead complex initiatives independently. It's a critical role for shaping product strategy and user experience at a high level.

Reporting Structure: While not explicitly stated, a Staff Designer typically reports to a Head of Product Design, VP of Product, or a similar senior leadership role. They will work very closely with Product Managers and Engineering Leads as strategic partners.

Operations Impact: This role has a direct and significant impact on Scale to Win's GTM operations. By designing intuitive and efficient tools for texting, dialing, and customer engagement, the designer directly influences the effectiveness of political campaigns and organizations. This includes:

• Sales Enablement: Designing tools that help sales teams communicate more effectively and manage outreach campaigns.

• Customer Success: Creating user-friendly interfaces that reduce onboarding friction and improve adoption rates for clients.

• Marketing Operations: Potentially influencing how campaign messaging is structured and deployed through the platform.

• Revenue Growth: By improving product usability and client success, the designer contributes to client retention, expansion, and overall revenue growth.

Growth Opportunities:

• Design Leadership: Opportunity to shape the design team's philosophy, processes, and standards, potentially leading to a Principal Designer or Design Lead role.

• Product Strategy Influence: Deep involvement in product roadmap decisions and the opportunity to influence the strategic direction of product development.

• Specialization: Develop deep expertise in niche areas like political tech, data visualization for campaigns, or AI-driven product features.

• Cross-functional Expertise: Gain extensive experience working with GTM functions, enhancing understanding of sales, marketing, and customer success operations.

• Mentorship: Opportunity to mentor and guide other designers as the team grows.

📝 Enhancement Note: This Staff Designer role is positioned to be highly influential, acting as a key architect of the user experience that directly supports the company's GTM strategy and revenue generation through its client base. The growth path leans towards strategic leadership within design and product.

🌐 Work Environment

Office Type: Fully Remote. Scale to Win is a fully-remote company, meaning there is no central physical office for this role.

Office Location(s): The role is based in Santa Ana, California, but operates remotely across the United States. This implies that while the company may have a legal presence or historical ties to Santa Ana, the day-to-day work environment is distributed.

Workspace Context:

• Asynchronous Collaboration: As a remote team, there will be a strong emphasis on asynchronous communication tools (e.g., Slack, email, project management software) and well-documented decision-making processes to facilitate collaboration across time zones.

• Technology Stack: Access to a robust set of design and collaboration tools will be provided, including a company computer and a home office stipend to ensure a productive work environment.

• Team Interaction: While remote, opportunities for virtual team building, design critiques, and cross-functional syncs will be integral to fostering a connected and collaborative atmosphere.

Work Schedule: The role is full-time, likely around 40 hours per week. The remote nature allows for flexible working conditions, enabling individuals to structure their day effectively while ensuring availability for critical meetings and collaborative sessions, particularly with teams potentially in different US time zones.

📝 Enhancement Note: The fully remote nature of this role requires self-discipline, excellent communication skills, and comfort with digital collaboration tools. The company's commitment to providing a home office stipend and computer supports a productive remote workspace.

📄 Application & Portfolio Review Process

Interview Process:

• Application Submission: Submit resume and application via the Ashby portal.

• Portfolio Review: Initial assessment of your portfolio to evaluate systems thinking, end-to-end design capabilities, and experience with complex B2B SaaS products.

• Initial Screen Interview: A brief introductory call to assess basic qualifications, cultural fit, and interest in the role and company.

• Hiring Manager Interview: A deeper dive into your experience, design philosophy, and how you approach problem-solving and collaboration.

• Design Interview: A technical interview focused on design craft, process, and strategic thinking, potentially involving a design exercise discussion.

• Panel Presentation & Cross-functional Interview: A more comprehensive session where you present a case study or solution, engaging with a panel including Product, Engineering, and GTM representatives. This assesses your ability to influence and communicate with diverse stakeholders.

• Co-CEO Meet & Greet: An opportunity to meet the company's top leadership and discuss the company vision and your potential contribution.

• Reference Check: Standard verification of your professional background and performance.

Portfolio Review Tips:

• Showcase Systems Thinking: Clearly articulate how your designs contribute to a larger, cohesive product ecosystem and address scalability. Use diagrams or flowcharts to illustrate system interactions.

• Demonstrate End-to-End Ownership: For each case study, detail your involvement from problem definition and user research through to final design delivery and impact.

• Highlight Ambiguity Navigation: Select projects where you faced significant technical or business challenges and explain your strategic approach to resolving them.

• Quantify Impact: Whenever possible, include metrics or qualitative feedback that demonstrate the positive impact of your design solutions on user behavior, efficiency, or business goals.

• Tailor to B2B SaaS & Political Tech: Emphasize projects that align with B2B SaaS complexities and, if possible, showcase experience with data visualization, messaging platforms, or campaign-related tools.

• Design Philosophy Articulation: Be prepared to discuss your personal design philosophy, how you approach user-centricity, accessibility, and the integration of new technologies like AI.

Challenge Preparation:

• Case Study Presentation: Prepare a compelling narrative for one or two key portfolio projects. Focus on the problem, your process, your decisions, and the outcomes. Practice presenting concisely within a set timeframe.

• Strategic Thinking: Be ready to discuss how you would approach designing for Scale to Win's specific product suite (texting, dialing) and how your designs can enhance GTM operations and client success.

• Stakeholder Management: Anticipate questions about how you collaborate with Product Managers, Engineers, and GTM teams, and how you handle conflicting priorities or feedback.

📝 Enhancement Note: The interview process is extensive, reflecting the seniority of the role. The emphasis on a portfolio review, a panel presentation, and cross-functional interviews highlights the need for strong communication, strategic thinking, and the ability to demonstrate impact on business objectives, particularly GTM operations.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable for modern design teams), Sketch, Adobe Creative Suite (Illustrator, Photoshop).

• User Research & Testing: UserTesting.com, Maze, Hotjar, Lookback.

• Design Systems: Tools for documentation and management (e.g., Zeroheight, Storybook integration).

• Collaboration & Project Management: Slack, Asana, Jira, Confluence.

Analytics & Reporting:

• Product Analytics: Google Analytics, Amplitude, Mixpanel, Tableau, Power BI (for understanding user behavior and product performance).

• CRM/Sales Data: Salesforce, HubSpot (for understanding client interactions and sales pipeline if integrated into product design).

CRM & Automation:

• CRM (Client-facing): While not directly a design tool, understanding how clients use CRMs like Salesforce or HubSpot within their own operations can inform design.

• Workflow Automation: Familiarity with how workflow automation tools might integrate with or be designed within the product.

📝 Enhancement Note: The role requires proficiency in standard modern design tools and a strong understanding of how design integrates with analytics, CRM, and potentially automation platforms to support GTM operations. Experience with data visualization tools is specifically mentioned as a preferred skill.

👥 Team Culture & Values

Operations Values:

• Customer-Centricity: A deep commitment to understanding and advocating for the user's needs, ensuring that product designs solve real problems and enhance user workflows.

• Impact-Driven: A focus on driving tangible results and making a meaningful difference, particularly within the political and organizing space. This translates to designing for effectiveness and campaign success.

• Collaboration & Influence: Valuing teamwork, open communication, and the ability to influence stakeholders across different functions to achieve shared goals.

• Excellence & Craftsmanship: Upholding high standards for design quality, attention to detail, and continuous improvement of design processes and outputs.

• Scalability & Resilience: Designing with a long-term perspective, building systems that are robust, adaptable, and can scale with the company's growth and evolving client needs.

Collaboration Style:

• Strategic Partnership: Working as a peer to Product and Engineering leadership, contributing to strategic decisions and vision.

• Cross-functional Integration: Actively engaging with Sales, Customer Success, and other GTM teams to gather insights and ensure product designs meet operational needs.

• Open Critique & Feedback: Fostering an environment where constructive feedback is shared openly to elevate the quality of design work across the team.

• Knowledge Sharing: Proactively sharing best practices, learnings, and design methodologies to uplift the entire product and design organization.

📝 Enhancement Note: The company's mission in political tech suggests a culture that is passionate, fast-paced, and impact-oriented. The values emphasize user advocacy, strategic alignment with business goals (including GTM), and collaborative problem-solving, which are crucial for a senior design role supporting operational efficiency.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Ambiguity: Operating in a fast-paced political tech environment with evolving client needs and potential technical constraints requires adaptability and strong problem-solving skills.

• Balancing Short-term vs. Long-term: The need to deliver on immediate product roadmaps while also architecting for a scalable, resilient long-term product ecosystem.

• Influencing Without Authority: As a senior individual contributor, effectively influencing Product and Engineering leadership and cross-functional teams to adopt design strategies.

• Evolving Design Craft: Continuously pushing the boundaries of design excellence and integrating emerging technologies like AI into user experiences within a growing company.

• Remote Collaboration Dynamics: Maintaining strong team cohesion and effective communication in a fully remote setting.

Learning & Development Opportunities:

• Strategic Design Leadership: Opportunity to define and lead the design vision for significant product areas, shaping the future of Scale to Win's offerings.

• Domain Expertise: Deepen understanding of the political tech landscape, campaign operations, and the unique challenges faced by progressive organizations.

• AI Integration: Gain hands-on experience designing with and for AI-powered features, staying at the forefront of technological advancements.

• Mentorship & Team Building: Play a key role in growing and mentoring a design team, contributing to its culture and processes.

• Professional Development Stipend: Utilize the annual $2,000 stipend for courses, conferences, books, or certifications relevant to advanced product design, GTM strategy, or emerging technologies.

📝 Enhancement Note: The challenges presented are typical for senior roles in innovative tech companies, particularly those in fast-moving sectors like political tech. The growth opportunities are significant, offering a path to strategic leadership and specialized expertise.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to design a complex system or product vertical from scratch. What was your process, what challenges did you face, and what was the outcome?" (Focus on systems thinking, end-to-end ownership, and handling ambiguity.)

• "How do you balance delivering on immediate product roadmap needs with architecting for long-term scalability and technical resilience?" (Assess your strategic prioritization and foresight.)

• "Walk us through a project where you had to gain buy-in for a bold or unconventional design direction from stakeholders who were resistant. What was your strategy?" (Evaluate your influence and communication skills.)

Company & Culture Questions:

• "Why are you interested in Scale to Win and the political tech space specifically?" (Showcase your understanding of the company's mission and market.)

• "How do you approach designing for accessibility and inclusivity in complex B2B SaaS products?" (Demonstrate your commitment to user-centered design principles.)

• "Describe your experience designing for data visualization or messaging platforms. How would you approach designing these features for our clients?" (Connect your skills to specific product areas.)

Portfolio Presentation Strategy:

• Structure Your Narrative: For each case study, clearly define the problem, your role and responsibilities, your design process (research, ideation, iteration, testing), the solutions you designed, and the impact/outcomes.

• Emphasize Systems Thinking: Use diagrams or visual aids to show how your designs fit into a larger system and how they contribute to scalability and long-term vision.

• Highlight GTM Relevance: If possible, frame your case studies in terms of how they improved user efficiency, client success, or operational effectiveness for the end-users (campaigns/organizations).

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

• Articulate Your Design Philosophy: Be ready to discuss your core beliefs about user experience, design ethics, and the role of design in technology.

📝 Enhancement Note: The interview process is designed to assess not only design skills but also strategic thinking, collaboration, and the ability to drive impact within a mission-driven, remote-first organization. Preparing case studies that highlight systems thinking and GTM relevance will be key.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your resume and application through the provided Ashby portal.

• Portfolio Customization: Curate your portfolio to prominently feature 2-3 case studies demonstrating end-to-end ownership of complex B2B SaaS product challenges, with a strong emphasis on systems thinking, scalability, and navigating ambiguity. Tailor your presentation to highlight how your designs have supported operational efficiency or GTM objectives.

• Resume Optimization: Ensure your resume clearly outlines your 10+ years of experience, specifically mentioning B2B SaaS, design systems, and leadership (even if through influence). Quantify achievements and responsibilities where possible, using keywords from the job description such as "systems thinking," "end-to-end product design," and "cross-functional partnerships."

• Interview Preparation: Practice articulating your design process, strategic decision-making, and collaborative approach. Prepare to present your portfolio case studies concisely and engage in deep discussions about your design philosophy and experience with remote collaboration.

• Company Research: Thoroughly research Scale to Win's mission, products (texting and dialing tools), client base (Democratic and progressive campaigns/organizations), and recent news. Understand the unique challenges and opportunities within the political tech space and how your design expertise can contribute to their GTM success and impact.

⚠️ 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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