Senior Product Designer at Pylon

📍 Job Overview

Job Title: Senior Product Designer

Company: Pylon

Location: San Francisco Bay Area, California, United States & New York City, New York, United States

Job Type: Full-Time

Category: Product Design

Date Posted: 2025-06-07T00:00:00

Experience Level: Senior (5+ years)

Remote Status: On-site

🎨 Role Summary

Lead the design of core product experiences for Pylon's Command Center (loan officer dashboard) and Elements (embeddable borrower application and dashboard), focusing on creating clear and intuitive interfaces within a complex, regulated financial environment.
Drive the evolution and maintenance of the design system, ensuring consistency, scalability, and high-quality UI/UX design across the entire product suite.
Collaborate closely with cross-functional teams including product management, engineering, and Go-to-Market to translate technical workflows into user-centered design solutions.
Contribute significantly to the development of Pylon's design culture, advocating for design principles and influencing product strategy from a user-centric perspective.

📝 Enhancement Note: The summary is enhanced to specifically highlight the core products (Command Center, Elements) and the challenge of designing for a regulated financial industry, which is key to this role's complexity and impact. It also emphasizes the strategic contribution expected from a Senior designer in shaping design culture and product direction.

🖼️ Primary Responsibilities

Design end-to-end product experiences, from initial concept and wireframing through to polished final UI, for both the Command Center and Elements platforms, ensuring seamless user flows for loan officers, borrowers, and operations teams.
Translate complex, abstract technical workflows and regulatory requirements into intuitive and user-friendly interfaces, making sophisticated financial decisions feel simple and accessible.
Take ownership of the design system, actively contributing to its evolution, documentation, and adoption to maintain design consistency, efficiency, and scalability across the product suite.
Work in tight partnership with product managers and engineers throughout the product development lifecycle, participating in scoping, prototyping, user testing, and shipping high-quality features.
Champion design quality and simplicity, meticulously refining every design element – from buttons and forms to data visualizations – to ensure clarity, usability, and a high standard of craftsmanship.
Actively participate in product vision, roadmap planning, and company strategy discussions, bringing a strong design voice and advocating for user needs and optimal user experience.
Help establish and nurture Pylon's design culture, promoting collaboration, continuous learning, and a shared commitment to design excellence within the organization.

📝 Enhancement Note: Responsibilities are broken down into more granular, actionable points, explicitly mentioning the specific platforms (Command Center, Elements) and user types (loan officers, borrowers, operations teams). The emphasis on translating complexity into simplicity and owning the design system highlights key challenges and expectations for a Senior-level role in this domain.

🎓 Skills & Qualifications

Education: While a Bachelor's degree in Design, HCI, or a related field is often preferred, equivalent practical experience and a strong portfolio demonstrating relevant skills and knowledge are highly valued in the design industry. Specific requirements are often flexible based on the candidate's track record.

Experience: Minimum of 5 years of professional product design experience is required. Ideal candidates will have experience designing complex software products, particularly within the fintech, enterprise, or infrastructure sectors. A robust portfolio showcasing successful projects, design process, and impact is essential.

Required Skills:

Proven expertise in end-to-end product design, including user research, wireframing, prototyping, interaction design, and visual design.
Strong proficiency in designing for complex, data-rich applications and translating abstract technical concepts into intuitive user interfaces, especially within regulated industries.
Extensive experience with design system ownership, evolution, and implementation to ensure design consistency and efficiency across a product suite.
Exceptional visual design skills and a strong portfolio demonstrating high-quality UI craft and attention to detail.
Proficiency in Figma for design, prototyping, and collaboration.
Demonstrated ability to collaborate effectively with engineers, product managers, and Go-to-Market teams throughout the product lifecycle.
Excellent communication and presentation skills, with the ability to clearly articulate design rationale and gather feedback effectively.

Preferred Skills:

Experience designing for financial services or mortgage industry-specific applications.
Familiarity with AI-assisted prototyping tools and workflows.
Experience conducting user research and usability testing to inform design decisions.
Knowledge of accessibility standards (WCAG) and designing for inclusive experiences.

📝 Enhancement Note: Education and experience requirements are framed with design industry context, acknowledging that practical experience and portfolio quality are often prioritized over formal degrees. Required and preferred skills are itemized, explicitly listing Figma proficiency and experience in regulated environments as critical requirements based on the original description.

🎨 Portfolio & Creative Requirements

Portfolio Essentials:

Showcase a minimum of 3-5 detailed case studies that highlight end-to-end design processes for complex product features or applications, ideally in fintech, enterprise, or regulated industries.
Clearly articulate the problem statement, your role in the project, the target users, design challenges, your design process (including research, ideation, iteration), key design decisions, and the impact of your work (e.g., usability improvements, business metrics).
Include examples of high-fidelity UI designs, interactive prototypes, and user flows, demonstrating strong visual design skills and attention to detail.
Provide a clear explanation of how you translated technical or regulatory constraints into user-friendly design solutions.

Process Documentation:

Document your approach to understanding complex problem spaces, including any research methods used (e.g., user interviews, competitive analysis, workflow mapping) and how findings informed your design direction.
Illustrate your ideation process, showing early sketches, wireframes, and low-fidelity prototypes, and explaining how you explored different design concepts.
Detail your iteration process, including how you incorporated feedback from stakeholders (product, engineering, Go-to-Market) and user testing into your designs.

📝 Enhancement Note: This section provides specific, actionable guidance for structuring a design portfolio for this role, emphasizing case studies, end-to-end process documentation, and demonstrating problem-solving within complex, regulated environments.

💵 Compensation & Benefits

Salary Range: Based on industry data for Senior Product Designer roles in the San Francisco Bay Area and New York City, and considering Pylon's funding and stage, the estimated salary range is $140,000 - $180,000 annually. This estimate is based on cost of living differences between the two locations, typical compensation for a Senior level with 5+ years of experience in fintech/enterprise design, and publicly available salary benchmarks for similar roles at venture-backed companies. Actual compensation may vary based on experience, skills, and negotiation.

Benefits:

Comprehensive health, dental, and vision insurance plans.
Potential for equity options, aligning employee incentives with company growth and success.
Retirement savings plan (e.g., 401k) with potential company match.
Generous paid time off and holiday schedule.
Opportunities for professional development and learning, including access to design conferences, workshops, and online courses.
Potential for a stipend for workspace setup or other work-from-home benefits if applicable (though this role is on-site).

Working Hours: Full-time employment, typically standard business hours. Flexibility may be required based on project deadlines and collaboration needs with teams across different time zones (Bay Area and NYC), common in fast-paced tech environments.

📝 Enhancement Note: A salary range is estimated based on regional data for San Francisco and New York City, considering local cost of living and typical compensation for a Senior Product Designer in the fintech/enterprise space. Benefits are listed with considerations for what might be particularly relevant to designers (e.g., professional development).

🎯Team & Company Context

🏢 Company & Design Culture

Industry: Pylon operates at the intersection of Financial Technology (FinTech) and Infrastructure, specifically targeting the mortgage industry. This market is characterized by complex regulations, established workflows, and a significant opportunity for technological disruption through API-first solutions.

Company Size: As a company with 51-200 employees (based on LinkedIn data), Pylon is likely in a growth stage. This size suggests a dynamic environment where individual contributions have significant impact, and designers may have opportunities to shape processes and culture more directly compared to larger organizations.

Founded: While the exact founding date is not provided, the company's backing by significant venture capital firms and presence across multiple US locations indicates it is a relatively young but rapidly scaling organization.

Team Structure:

The design team is likely lean, especially in a company of this size, offering significant ownership and influence to Senior-level designers.
Close collaboration is expected with product management, engineering, and Go-to-Market teams, indicating a cross-functional approach to product development.
Given the on-site requirement in two distinct locations (Bay Area and NYC), there may be opportunities for in-person collaboration within those hubs, and potentially cross-site collaboration using digital tools.

Methodology:

Given the focus on user needs and translating complexity, Pylon likely employs user-centered design principles and methodologies.
A fast-paced, ambiguous environment suggests an agile or iterative development process, where designers are integrated into sprints and regularly collaborate with engineering.
Experience with prototyping and user feedback cycles is crucial, indicating a focus on validating design solutions with users.

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

📝 Enhancement Note: Company information is integrated with design-specific context, explaining what the industry, company size, and stage mean for a design professional. Assumptions about team structure and methodology are made based on the company's size, industry, and the nature of the role (e.g., fast-paced, collaborative).

📈 Career & Growth Analysis

Design Career Level: This is a Senior Product Designer role, indicating expectations of significant autonomy, leadership in design initiatives, and the ability to mentor or guide less experienced designers. Senior designers at this level are typically responsible for tackling complex design challenges and influencing product direction.

Reporting Structure: While not explicitly stated, a Senior Product Designer would likely report to a Design Lead, Head of Design, or potentially a Product Lead in a smaller organization. The reporting structure will influence the level of autonomy and strategic input expected.

Design Impact: As a Senior designer focusing on core product experiences (Command Center, Elements), you will have a direct impact on the usability, adoption, and success of Pylon's platform for both their clients (originators) and end-users (borrowers). Your work will be critical in simplifying complex financial processes. The role also mentions contributing to brand design, suggesting impact on the overall visual identity and market perception.

Growth Opportunities:

Potential for growth into a Lead Product Designer or Design Manager role as the design team expands with the company's growth.
Opportunity to specialize in specific areas such as FinTech UX, complex data visualization, or design system architecture.
Development of leadership skills through mentoring junior designers and leading design initiatives.
Deepening expertise in the mortgage and lending industry, becoming a domain expert in designing for complex financial workflows.

📝 Enhancement Note: This section provides a detailed analysis of the career level, explaining the expectations and potential growth paths for a Senior Product Designer within a growing tech company setting. The potential for impact on core products and brand is highlighted.

🌐 Work Environment

Studio Type: This role is on-site in either San Francisco or New York City. This suggests a traditional office-based work environment, promoting in-person collaboration.

Office Location(s): San Francisco Bay Area, California and New York City, New York. Candidates must reside in or be willing to relocate to one of these metropolitan areas. Both locations are major tech hubs with active design communities.

Design Workspace Context:

Working on-site provides opportunities for spontaneous collaboration with product, engineering, and other teams, facilitating faster feedback loops and shared understanding.
Access to dedicated meeting spaces, potentially whiteboarding areas, and physical resources conducive to collaborative design work.
Opportunities for in-person design critiques and workshops, fostering a strong team bond and shared design culture.

Work Schedule: Full-time, likely following a standard office schedule. The fast-paced nature of the environment may occasionally require flexibility to meet project deadlines.

📝 Enhancement Note: The work environment section focuses on the implications of an on-site role in major tech hubs, highlighting the benefits of in-person collaboration and potential access to office resources relevant to design work.

📄 Application & Portfolio Review Process

Design Interview Process:

Initial Screen: Expect a conversation with a recruiter or hiring manager to discuss your background, experience, and interest in the role, with a focus on your experience in product design and complex domains.
Portfolio Review: A dedicated session to walk through your portfolio case studies, focusing on your design process, problem-solving approach, collaboration skills, and the impact of your work, particularly on complex projects. Be prepared to discuss the challenges of designing for regulated environments.
Design Challenge or Whiteboarding Session: You may be given a design challenge (either take-home or live whiteboarding) to assess your problem-solving skills, design thinking, and ability to articulate your design process under time constraints. The challenge will likely involve a scenario related to complex workflows or data visualization.
Team Interviews: Interviews with key stakeholders including Product Managers, Engineering Leads, and other members of the design team to assess collaboration style, technical understanding, and cultural fit.
Final Round: Potential conversations with leadership (e.g., Head of Product, CEO) to discuss your strategic thinking, leadership potential, and alignment with company vision and values.

Portfolio Review Tips:

Select case studies that best demonstrate your experience designing for complex systems, data-rich interfaces, and regulated industries, as highlighted in the job description.
Structure your case studies to clearly articulate the problem, your role, your design process (including research, ideation, and iteration), key decisions, and the impact of your designs.
Focus on showcasing your ability to simplify complex workflows and present information clearly and intuitively. Highlight examples of translating technical requirements or regulatory constraints into user-friendly designs.
Be prepared to discuss trade-offs made during the design process and how you collaborated with engineering and product.

Challenge Preparation:

If given a take-home challenge, manage your time effectively and document your process thoroughly, not just the final solution.
For whiteboarding sessions, practice clearly articulating your thought process as you work through the problem. Focus on understanding the core problem, exploring different solutions, and explaining your rationale.
Be prepared to ask clarifying questions and engage in a collaborative discussion during the challenge.

ATS Keywords: Product Design, UX Design, UI Design, Senior Product Designer, Figma, Prototyping, Design System, FinTech, Enterprise Design, Infrastructure Design, Regulatory Compliance, Complex Workflows, Information Architecture, Interaction Design, Visual Design, User Research, Usability Testing, Collaboration, Cross-functional Teams, Design Thinking, Agile, Iterative Design, Problem Solving, Craftsmanship, Simplicity, Data Visualization, Mortgage Industry, API Design, Command Center, Elements, Brand Design, Communication, Stakeholder Management, Portfolio, Case Studies, Wireframing, User Flows, Design Critique.

📝 Enhancement Note: The application process is detailed with specific steps common for design roles, including portfolio review and design challenges. Tactical advice is provided for preparing for each stage, with a strong emphasis on showcasing relevant experience in complex domains and demonstrating the design process through case studies. A comprehensive list of ATS keywords is provided for resume optimization.

🛠 Tools & Technology Stack

Primary Design Tools:

Figma: Required proficiency for UI design, prototyping, and collaborative design work. Expected to be comfortable with advanced features and team library management for the design system.
AI Prototyping Tools: Familiarity with and comfort using AI-assisted prototyping tools is mentioned, indicating Pylon may be exploring or utilizing these in their workflow.

Collaboration & Handoff:

Tools for collaboration with product managers and engineers (e.g., Slack, Jira, Asana).
Tools for design handoff to engineering, potentially integrated with Figma (e.g., Zeplin, Abstract, or built-in Figma features).
Tools for documentation and design system management (e.g., Confluence, Notion, or dedicated design system platforms).

Research & Testing:

Tools for user research (e.g., Dovetail, Notion, or simple documentation tools).
Tools for usability testing and gathering user feedback (e.g., Maze, UserTesting.com, or internal methods).
Potential use of analytics platforms (e.g., Amplitude, Mixpanel) to inform design decisions and measure impact.

📝 Enhancement Note: Specific design tools and categories of tools are listed, with Figma highlighted as a required skill. The inclusion of AI prototyping tools reflects a potential area of interest for the company. Collaboration and research tools are inferred based on standard design workflows in a tech company.

👥 Team Culture & Values

Design Values:

Customer Obsession: A core company value emphasizing building for and ensuring the success of their customers (originators) and their borrowers. This translates to a design focus on user needs, usability, and delivering value.
Principled Opinions & Debate: A culture that encourages vigorous discussion and debate around decisions, including design choices. Designers are expected to have strong opinions and be able to articulate and defend their design rationale.
High Standards & Craftsmanship: A deep commitment to quality, precision, and thoughtful detail in design work. Every element should be intentional and contribute to a clean, powerful user experience.
Simplicity in Complexity: A key challenge and value is making sophisticated financial decisions and complex regulatory workflows feel simple and intuitive through design.

Collaboration Style:

Close partnership and integrated workflow with product managers and engineers throughout the design and development process.
Openness to vigorous discussion and debate, requiring strong communication and ability to defend design decisions while also being receptive to feedback.
Focus on cross-functional collaboration with Go-to-Market teams to ensure the product experience aligns with overall business strategy and customer needs.

📝 Enhancement Note: This section translates the "About You" points from the original description into specific design values and collaboration styles, explaining what these mean in practice for a designer at Pylon (e.g., customer obsession translates to user-centered design).

⚡ Challenges & Growth Opportunities

Design Challenges:

Simplifying Complexity: A primary challenge will be designing intuitive interfaces for highly complex and regulated financial workflows in the mortgage industry. This requires deep understanding of user needs and domain constraints.
Balancing Speed and Quality: Working in a fast-paced, ambiguous environment where velocity matters means balancing the need for rapid iteration with maintaining high standards of craftsmanship and thoughtful design.
Evolving a Design System: Taking ownership of and evolving a design system in a growing company requires strategic thinking, collaboration, and potentially influencing adoption across different teams.
Defining Design Culture: Contributing to and shaping the design culture from the ground up requires proactive leadership, advocacy for design principles, and potentially mentoring others.

Learning & Development Opportunities:

Gaining deep expertise in the FinTech and mortgage industries, becoming a specialist in designing for complex financial processes and regulatory environments.
Developing leadership and mentorship skills by influencing product strategy and potentially guiding other designers.
Enhancing skills in designing and managing scalable design systems.
Opportunity to work with and potentially influence the integration of AI prototyping tools into the design workflow.

📝 Enhancement Note: This section explicitly outlines the key design challenges inherent in the role (simplifying complexity, fast-paced environment, design system ownership) and connects them to specific growth opportunities, providing candidates with a realistic view of what to expect.

💡 Interview Preparation

Design Process Questions:

Be prepared to walk through your end-to-end design process for a complex project, highlighting how you approached understanding the problem, conducted research (if applicable), ideated, iterated, and collaborated with stakeholders. Use examples from your portfolio.
Discuss a time you had to design for a regulated or complex environment. Explain the challenges you faced and how you navigated them to create a user-friendly solution.
Describe your approach to gathering and incorporating feedback from engineers, product managers, and users into your designs.

Company Culture Questions:

Research Pylon's mission, products (Command Center, Elements), and the mortgage industry. Be prepared to discuss why you are interested in designing for this specific domain and company.
Reflect on the described values (customer obsession, principled opinions, high standards) and be ready to share examples of how you embody these in your work.
Ask thoughtful questions about the design team structure, collaboration within the company, and the biggest design challenges they are currently facing.

Portfolio Presentation Strategy:

Curate your portfolio specifically for this role, focusing on 2-3 case studies that best demonstrate your experience with complex UIs, enterprise/FinTech products, and design systems.
Structure your case study presentation to be concise and impactful, clearly stating the problem, your role, process, solution, and impact.
Practice presenting your case studies, focusing on storytelling and clearly articulating your design decisions and rationale. Be prepared for questions and be ready to discuss alternative approaches you considered.

📝 Enhancement Note: Interview preparation advice is tailored to the specific requirements of the role and company culture, providing concrete examples of questions to anticipate and strategies for preparing portfolio presentations and design challenges.

📌 Application Steps

To apply for this design position:

Submit your application through this link.
Tailor your resume and cover letter to highlight your relevant experience in product design, especially your work on complex interfaces, FinTech or enterprise products, and experience in regulated environments. Use keywords from the "ATS Keywords" section.
Ensure your online portfolio is up-to-date and easily accessible. Select case studies that demonstrate your end-to-end design process and ability to simplify complex workflows, specifically relevant to the challenges mentioned in this description.
Prepare to articulate your design process clearly and concisely during interviews, focusing on problem-solving, collaboration, and the impact of your work.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and design industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

Senior Product Designer