Staff Product Designer, Acquiring & Design System

📍 Job Overview

Job Title: Staff Product Designer, Acquiring & Design System

Company: Checkout.com

Location: London, England, United Kingdom

Job Type: FULL_TIME

Category: Product Design / Design Systems

Date Posted: 2026-08-06

Experience Level: 10+ years

Remote Status: Hybrid (3 days in office)

🚀 Role Summary

• Lead end-to-end product design for the Acquiring domain, focusing on enhancing user experience and driving adoption for merchants.

• Evolve and maintain Checkout.com's comprehensive cross-pillar design system, ensuring consistency and scalability across all products and surfaces.

• Drive significant improvements in design-to-development workflows, leveraging AI-integrated tools to accelerate product delivery cycles.

• Mentor and elevate the craft quality of fellow designers within the Acquiring product team and design system guild.

📝 Enhancement Note: This role is a blend of deep product ownership within a critical business domain (Acquiring) and strategic influence over the company's design system. The "Staff" title implies a need for significant autonomy, strategic thinking, and the ability to influence direction without formal management authority, particularly in technical fluency and AI adoption. The focus on "code-first" and "AI-integrated workflows" suggests a forward-thinking approach to design operations and product development.

📈 Primary Responsibilities

• Take full design ownership of the Acquiring product suite, from initial concept and user research through to final implementation and post-launch analysis.

• Lead the strategic evolution of Checkout.com's design system, ensuring its application and growth across diverse product areas including dashboard and mobile interfaces.

• Collaborate closely with Product Managers and Engineering teams to translate complex product requirements into elegant, user-centered design solutions that adhere to system standards.

• Develop and refine design-to-development workflows, integrating AI-assisted tools and processes to streamline implementation and improve efficiency for design and engineering teams.

• Mentor and provide constructive design critique to other designers, fostering a culture of high craft quality and continuous improvement within the Acquiring team and the broader design organization.

• Identify and address design coverage gaps within the Acquiring product area and across the design system.

• Champion the adoption and effective use of the design system and AI tooling by product teams.

📝 Enhancement Note: The responsibilities highlight a dual focus: tactical execution within a specific product area (Acquiring) and strategic leadership in design system development and process innovation. The emphasis on "shipping code" and "AI-integrated workflows" indicates a need for designers who are not only skilled in traditional design disciplines but also understand technical implementation and are eager to leverage emerging technologies to improve operational efficiency.

🎓 Skills & Qualifications

Education: Bachelor's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience.

Experience: 10+ years of progressive experience in product design, with a proven track record of leading complex product initiatives and evolving design systems.

Required Skills:

• Staff-level product design scope: Demonstrated ability to set design direction, influence stakeholders, and elevate the quality of design work across a team without formal authority.

• Exceptional product craft: Mastery in interaction design, visual design, prototyping, and delivering user-centered experiences that have been successfully shipped.

• Complex product ownership: Experience managing intricate product work streams, from problem definition through to successful delivery in partnership with Product and Engineering.

• Design system leadership: Proven experience in shaping, evolving, and scaling a production-ready design system across multiple products and platforms.

• Technical fluency: Ability to collaborate effectively with engineering teams on implementation constraints, design-to-development handoffs, and workflow optimization. This is not a front-end engineering role, but understanding technical feasibility is crucial.

• AI-assisted workflow experience: Hands-on experience with AI tools for design or development (e.g., Claude Code, Cursor, or similar), demonstrating an understanding of their application in modern product development. Preferred Skills:

• Payments or Fintech industry experience: Familiarity with the unique challenges and opportunities in the payments and financial technology sectors.

• B2B SaaS product experience: Experience designing for business-to-business software solutions, particularly those with complex workflows and enterprise clients.

• Experience with enterprise, platform, or infrastructure products: Designing for technically demanding systems and complex user needs in large organizations.

• Design system guild leadership: Experience in leading design system initiatives, improving cross-team design quality, and managing design across desktop and mobile interfaces.

📝 Enhancement Note: The "Staff-level" requirement emphasizes leadership and influence. The "technical fluency" and "AI-assisted workflow" requirements point towards a need for designers who are not afraid of technical details and are proactive in adopting new technologies to improve efficiency. The "nice to have" section indicates that experience in Payments, Fintech, or B2B SaaS is highly valued due to the nature of Checkout.com's business.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase end-to-end product design case studies demonstrating ownership of complex problems, from discovery through to shipped solutions.

• Highlight significant contributions to the evolution and application of a production design system, illustrating its impact on consistency and efficiency.

• Include examples of how you've improved design-to-development workflows, ideally with insights into how AI or automation was integrated.

• Demonstrate exceptional craft in interaction and visual design, with clear articulation of design decisions and their rationale.

• Present examples of mentoring or guiding other designers, showcasing your ability to raise design quality within a team. Process Documentation:

• Case studies should clearly outline the design process followed, including research methodologies, ideation techniques, prototyping, user testing, and iteration.

• Detail the specific challenges encountered in applying or evolving a design system and the strategic solutions implemented.

• Document how collaboration with Product and Engineering was managed, particularly concerning technical constraints and workflow optimization.

• Illustrate the impact of your work using quantifiable metrics where possible (e.g., improved conversion rates, reduced design debt, faster iteration cycles).

📝 Enhancement Note: For a Staff-level role focused on both product ownership and design systems, the portfolio is critical. It needs to demonstrate not just design skills but also strategic thinking, technical understanding, and leadership potential. Emphasis should be placed on how the candidate has driven process improvements and influenced design operations, particularly concerning the design system and AI integration.

💵 Compensation & Benefits

Salary Range: Based on industry benchmarks for Staff Product Designer roles in London with 10+ years of experience in the fintech/SaaS sector, the estimated salary range is £90,000 - £130,000 per annum. This range is subject to candidate experience, specific qualifications, and the company's internal compensation structure.

Benefits:

• Competitive salary and performance-based bonuses.

• Comprehensive health insurance coverage.

• Generous pension scheme.

• Life assurance and income protection.

• Professional development budget for conferences, training, and courses.

• Opportunities for stock options or equity.

• Generous paid time off and public holiday allowance.

• Enhanced parental leave policies.

• Wellness programs and resources.

• Hybrid working model with office days to foster collaboration.

Working Hours: Standard full-time hours (approximately 40 hours per week), with flexibility to accommodate project needs. The hybrid model requires 3 days per week in the London office.

📝 Enhancement Note: Salary ranges for Staff Product Designers in London are competitive, especially in the fintech sector. The provided estimate is based on publicly available data for similar roles and experience levels in the UK market, considering Checkout.com's position as a major fintech player. The benefits package is expected to be robust, reflecting the company's commitment to attracting and retaining top talent in a competitive market.

🎯 Team & Company Context

🏢 Company Culture

Industry: Fintech / Payments Technology. Checkout.com operates at the forefront of global digital payments, enabling businesses worldwide to process transactions online. This fast-paced industry demands innovation, reliability, and a deep understanding of complex financial systems and regulatory environments.

Company Size: Checkout.com is a rapidly growing, large-scale organization with over 2,000 employees across multiple continents, indicating a structured yet dynamic environment.

Founded: Founded in 2012, Checkout.com has established itself as a significant player in the fintech space, demonstrating a history of sustained growth and product development.

Team Structure:

• The Design organization is a substantial unit of 30+ specialists, encompassing Product Design, Research, Content, and Technical Writing, fostering a collaborative and specialized environment.

• This role is embedded within the Product Design function, reporting to the Director of Enterprise Product Design.

• The designer will work closely with Product Managers, Engineers, and potentially other design system contributors across various product pillars. Methodology:

• Emphasis on data-driven decision-making and user-centered design principles.

• A "code-first" approach to design systems suggests a strong emphasis on practical implementation and close collaboration with engineering.

• Integration of AI-assisted workflows indicates a commitment to leveraging cutting-edge technology for efficiency and innovation in product development.

• Focus on end-to-end product delivery, from ideation to shipped code, demanding strong cross-functional collaboration.

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

📝 Enhancement Note: Checkout.com's culture is described as one that supports high performers, offers ownership, and minimizes blockers. The "bring all of you to work" motto suggests an inclusive environment that values individual contributions. The hybrid model and emphasis on collaboration indicate a company that balances flexibility with the need for in-person interaction, particularly for strategic roles.

📈 Career & Growth Analysis

Operations Career Level: Staff Product Designer. This level signifies a senior individual contributor role, characterized by significant autonomy, the ability to influence strategic direction, and the responsibility for mentoring and raising the bar for design quality across teams. It's a critical role for driving product innovation and operational efficiency through design.

Reporting Structure: Reports to the Director of Enterprise Product Design. This senior leadership position provides strategic guidance and oversight, while the Staff Designer is expected to operate with a high degree of independence on their assigned domains.

Operations Impact: This role has a direct impact on Checkout.com's core business operations by:

• Enhancing the user experience for merchants using the Acquiring platform, directly influencing transaction success rates and customer satisfaction.

• Accelerating product delivery and ensuring design consistency across the company through the design system, which improves engineering efficiency and reduces development debt.

• Driving the adoption of advanced technologies like AI in design and development workflows, contributing to operational efficiency and competitive advantage. Growth Opportunities:

• Deep specialization in the payments/fintech domain and complex enterprise SaaS products.

• Leadership opportunities in evolving the company's design system and advocating for design best practices across engineering and product teams.

• Potential to grow into Principal or Lead Designer roles, or move into management positions overseeing design teams.

• Exposure to cutting-edge AI technologies within a product development context.

• Opportunities to influence strategic product decisions and shape the future of Checkout.com's platform.

📝 Enhancement Note: The Staff level is a significant step up from Senior Designer, requiring strategic thinking and the ability to operate with less direct supervision. The growth path is typically towards Principal Designer, Architecture Lead, or a management track, focusing on broader organizational impact and technical/strategic leadership. The hybrid nature of the role, involving both product ownership and design system evolution, offers a well-rounded development path.

🌐 Work Environment

Office Type: Checkout.com operates with a hybrid working model, requiring 3 days a week in their London office. This suggests a modern, collaborative office space designed to facilitate teamwork, brainstorming, and cross-functional interactions.

Office Location(s): The role is based in the London office. Specific details about the office's amenities and location within London would be available upon inquiry or during the interview process.

Workspace Context:

• The office environment likely supports collaborative work, with meeting rooms, breakout spaces, and open-plan areas conducive to design critique sessions and team discussions.

• Access to relevant design and development tools, software, and potentially specialized hardware for prototyping or testing will be provided.

• Opportunities for direct interaction with Product Managers, Engineers, Researchers, and fellow designers, fostering a dynamic and integrated work environment.

Work Schedule: The standard working hours are approximately 40 hours per week, with the expectation of flexibility to meet project demands. The hybrid model allows for a balance between focused individual work at home and collaborative in-office activities.

📝 Enhancement Note: The hybrid model is a key feature, indicating a company that values work-life balance while recognizing the importance of in-person collaboration for complex roles like this. The London office is likely a hub for innovation and collaboration within the company's global network.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A recruiter will review your application and portfolio, assessing your alignment with the core requirements and experience.

• Portfolio Presentation & Discussion: You will likely present 2-3 key case studies from your portfolio to a panel of designers and potentially a Product Manager. This will focus on your design process, craft, technical fluency, and experience with design systems and AI.

• Design Challenge/Workshop: A practical exercise, potentially involving a design problem related to Acquiring or the design system, or a collaborative workshop to assess your problem-solving and collaboration skills.

• Hiring Manager Interview: A discussion with the Director of Enterprise Product Design to assess strategic thinking, leadership potential, and cultural fit.

• Cross-functional Interviews: Meetings with Engineering leads and Product Managers to evaluate collaboration style and technical understanding.

• Final Round: Potential discussions with senior leadership to confirm fit and alignment.

Portfolio Review Tips:

• Curate Strategically: Select case studies that best demonstrate your experience with complex products, design systems, AI workflows, and your ability to lead design initiatives.

• Show, Don't Just Tell: Clearly articulate your role, the problem, your process, the solutions you designed, and the impact achieved. Use visuals effectively.

• Highlight Technical Fluency: Be prepared to discuss how you collaborate with engineers, understand implementation constraints, and contribute to design-to-development workflows.

• Emphasize Design System Impact: Detail your contributions to design system evolution, adoption, and its quantifiable benefits.

• Demonstrate AI Integration: Showcase specific examples of how you've used AI tools to improve your design process or development outcomes.

• Prepare for Mentoring Discussions: Be ready to discuss how you provide design critique and mentor junior designers.

Challenge Preparation:

• Familiarize yourself with Checkout.com's products, particularly their Acquiring services, and the general fintech landscape.

• Review common design system challenges and best practices for AI integration in design.

• Practice articulating your design process and decisions clearly and concisely, focusing on impact and rationale.

• Prepare questions that demonstrate your strategic thinking and interest in the role and company.

📝 Enhancement Note: The interview process for a Staff-level role will be rigorous, focusing heavily on strategic thinking, leadership, and practical application of skills. A strong, well-curated portfolio is paramount, and candidates should be prepared to deeply discuss their contributions and impact. The emphasis on AI and design systems suggests these will be key areas of evaluation.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly likely given industry standard), Sketch, Adobe Creative Suite.

• Prototyping Tools: InVision, Principle, Framer (for advanced interactions).

• AI Design Tools: Claude Code, Cursor, or similar AI-assisted coding/design assistants.

Analytics & Reporting:

• Google Analytics, Amplitude, Mixpanel, or similar product analytics platforms for understanding user behavior and product performance.

• Tableau, Looker, or Power BI for dashboard creation and reporting. CRM & Automation:

• While not a direct responsibility, understanding of CRM systems like Salesforce or HubSpot might be beneficial for context within B2B SaaS.

• Familiarity with project management tools like Jira, Asana, or Trello for workflow tracking.

📝 Enhancement Note: While specific tools aren't listed, Figma is the industry standard for product design. The mention of AI-assisted tools like Claude Code and Cursor is a critical requirement. Proficiency in product analytics and a general understanding of development workflow tools are also expected for a role of this caliber.

👥 Team Culture & Values

Operations Values:

• Impact-Driven: A strong focus on delivering tangible results that drive business growth and operational efficiency.

• Collaboration: Valuing cross-functional teamwork, open communication, and mutual support among designers, product, and engineering.

• Innovation: Encouraging the exploration of new technologies and methodologies, such as AI integration, to stay ahead in the fintech space.

• Craftsmanship: A commitment to high-quality design execution, attention to detail, and user-centered problem-solving.

• Ownership: Empowering individuals to take responsibility for their work and drive initiatives forward with autonomy.

• Growth Mindset: Fostering continuous learning, skill development, and adaptability in a rapidly evolving industry.

Collaboration Style:

• Highly collaborative, with regular interaction across Product, Engineering, and other Design disciplines.

• Emphasis on constructive critique and feedback loops to ensure the highest quality outcomes.

• A "code-first" approach to design systems implies a very tight integration and partnership with engineering teams.

• Open communication channels are encouraged to facilitate problem-solving and knowledge sharing.

📝 Enhancement Note: Checkout.com's values appear to align with a high-performance culture that prioritizes impact, innovation, and teamwork. The specific mention of "code-first" and "AI-integrated workflows" suggests a practical, execution-oriented approach to design operations and product development.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing dual responsibilities: Effectively managing lead design for Acquiring while simultaneously driving the evolution of a complex, cross-pillar design system requires strong time management and prioritization skills.

• Influencing without authority: As a Staff Designer, you'll need to lead and inspire through expertise and collaboration rather than direct management, requiring strong communication and stakeholder management skills.

• Technical complexity: Working within the fintech/payments domain and on infrastructure-level products involves understanding intricate technical details and regulatory requirements.

• Evolving design-to-development workflows: Integrating AI and optimizing these processes across multiple teams can be challenging and requires strong change management skills. Learning & Development Opportunities:

• Deepen expertise in the payments and fintech industry, a high-growth and complex sector.

• Become a subject matter expert in design systems and their application in large-scale, enterprise products.

• Gain hands-on experience and leadership in leveraging AI tools for design and development efficiency.

• Develop strategic leadership skills through influencing product direction and design operations.

• Opportunities for professional development, attending industry conferences, and pursuing relevant certifications.

📝 Enhancement Note: The primary challenge lies in the breadth and depth of the role – being a strategic leader for the design system and a hands-on owner for a critical product area. The growth opportunities are significant for someone looking to advance their career in a leading fintech company, with a focus on cutting-edge design practices and technologies.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you led the evolution of a design system. What were the biggest challenges, and how did you overcome them? What was the impact on product delivery?"

• "How do you approach balancing ownership of a specific product area with your responsibilities for a company-wide design system?"

• "Walk us through your process for collaborating with engineering to ensure design-to-development workflows are efficient and effective, especially with AI integration."

• "Describe a complex product problem you solved. What was your approach, what trade-offs did you make, and how did you measure success?"

• "How do you mentor and elevate the design craft of other designers?" Company & Culture Questions:

• "What interests you most about Checkout.com and the fintech industry?"

• "How do you see the role of AI evolving in product design, and how have you applied it in your work?"

• "Describe your ideal work environment and how you contribute to a positive team culture."

• "How do you handle ambiguity and prioritize tasks when faced with multiple competing demands?" Portfolio Presentation Strategy:

• Structure: For each case study, clearly define the problem, your role, the process, the solution, and the impact. Use a chronological or thematic approach.

• Focus on Impact: Quantify results whenever possible (e.g., increased conversion, reduced error rates, faster development cycles).

• Highlight Design System & AI: Dedicate specific sections or discussion points to your contributions to the design system and any AI tools you've utilized.

• Show Technical Fluency: Be prepared to discuss implementation details, collaboration with engineers, and any technical constraints you navigated.

• Craft & Rationale: Be ready to defend your design decisions and explain the rationale behind your UI/UX choices.

• Engage: Ask thoughtful questions to the interviewers to show your engagement and understanding of the role and company.

📝 Enhancement Note: The interview process will heavily scrutinize your ability to think strategically, lead through influence, and demonstrate practical expertise in design systems and AI. Prepare case studies that explicitly address these areas and be ready to discuss your thought process in detail.

📌 Application Steps

To apply for this Staff Product Designer position:

• Submit your application through the provided link on Ashby.

• Portfolio Customization: Tailor your portfolio to highlight your most relevant work, specifically focusing on complex product design, design system contributions, and any experience with AI-assisted workflows or B2B SaaS/Fintech products. Ensure case studies clearly articulate your role, process, and impact.

• Resume Optimization: Ensure your resume clearly states your years of experience, highlights key achievements relevant to staff-level responsibilities (e.g., setting direction, mentoring, driving process improvements), and includes keywords like "Product Design," "Design Systems," "AI-assisted Workflows," and "Fintech."

• Interview Preparation: Thoroughly review your selected case studies, practice articulating your design process and rationale, and prepare specific examples of how you've mentored others and improved design-to-development workflows. Research Checkout.com's products and company values.

• Company Research: Understand Checkout.com's position in the fintech market, their key products (especially Acquiring), and their stated company values. This will help you tailor your responses and ask insightful questions.

⚠️ 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.