PRODUCT MANAGEMENT - Sr Product Designer

📍 Job Overview

Job Title: Sr. Product Designer

Company: Stretto, Inc.

Location: United States

Job Type: Full-Time

Category: Product Design / UX

Date Posted: 2026-04-23T07:00:00

Experience Level: Mid-Senior Level (5-10 years)

Remote Status: Remote OK (US-based candidates preferred)

🚀 Role Summary

• Lead end-to-end product design and UX strategy for complex cloud-based B2B and B2C products, directly impacting core business outcomes in the bankruptcy ecosystem.

• Drive product direction and champion design thinking across Stretto's product portfolio, ensuring high-quality, efficiency-driven solutions for legal professionals and their clients.

• Collaborate closely with Product and Engineering leadership to influence roadmaps, prioritize initiatives, and define product strategy, leveraging user insights and business objectives.

• Champion user advocacy while balancing critical regulatory, technical, and business constraints within a complex stakeholder environment.

📝 Enhancement Note: This role is positioned as a senior individual contributor, requiring a strong blend of design craft, strategic thinking, and the ability to navigate complex stakeholder dynamics. The emphasis on AI tools and AI-powered experiences indicates a forward-thinking approach to product development within Stretto's operational strategy.

📈 Primary Responsibilities

• Own and lead design efforts for assigned product areas, demonstrating a high degree of autonomy and design craftsmanship.

• Partner with Product Managers and Engineering Leads to inform and influence product roadmap prioritization and overall product strategy.

• Effectively communicate design rationale, trade-offs, and vision to a diverse range of stakeholders, including executives, subject matter experts (SMEs), client success managers (CSMs), clients, and internal teams, driving toward alignment.

• Identify and champion both short-term and long-term product and UX improvements, grounding recommendations in robust user needs analysis and measurable business impact.

• Define, track, and report on key UX metrics that directly correlate design outcomes with tangible business results, demonstrating the value of design.

• Collaborate effectively across the entire product lifecycle, from discovery and research through to delivery and iteration, ensuring seamless integration of design.

• Plan, facilitate, and lead workshops for critical activities such as strategic alignment, user discovery, and creative ideation sessions.

• Conduct and synthesize both qualitative and quantitative user research to deeply inform product strategy and validate proposed solutions.

• Deliver comprehensive, end-to-end design solutions, encompassing user journeys, flow diagrams, wireframes, interactive prototypes, and high-fidelity visual designs.

• Actively leverage AI tools (e.g., ChatGPT, Claude, Figma AI) to accelerate workflows across research, ideation, content creation, and prototyping phases.

• Contribute to the design and definition of AI-powered product experiences in close collaboration with Product Management and Engineering teams.

• Actively contribute to the development, maintenance, and evolution of the Stretto Design System and overall design best practices.

• Provide constructive, actionable feedback to design peers and actively support a collaborative and high-performing design culture.

• Advocate for the end-user throughout the design process while adeptly balancing regulatory, technical, and business constraints.

• Contribute to the scoping, planning, and estimation of design efforts, ensuring realistic timelines and resource allocation.

• Perform other duties as assigned to support the broader product and design team objectives.

📝 Enhancement Note: The responsibilities highlight a senior role with significant ownership. The integration of AI tools and the focus on AI-powered experiences suggest a need for designers comfortable with emerging technologies and their application in enterprise software. Emphasis on UX metrics and linking design to business outcomes is crucial for demonstrating impact.

🎓 Skills & Qualifications

Education: Bachelor’s degree in Interaction Design, Human-Computer Interaction (HCI), Graphic Design, or a related discipline. A Master's degree is preferred. Equivalent practical experience will also be considered.

Experience: 5-7+ years of progressive experience in product design, UX design, or interaction design.

Required Skills:

• Proven experience designing complex, cloud-based B2B and B2C software products, with a strong preference for experience in FinTech or similarly regulated industries.

• Demonstrated ability to connect design decisions directly to business goals and make sound, well-reasoned trade-offs.

• Comfort and proficiency in influencing cross-functional stakeholders through clear communication, compelling design rationale, and strategic negotiation.

• Extensive experience working with complex, data-heavy interfaces and large-scale information systems.

• Solid competency across the full UX spectrum, including user research, information architecture (IA), interaction design, prototyping, visual design, and overall design strategy.

• Strong knowledge of accessibility standards (WCAG) and best practices for inclusive design.

• Experience contributing to and utilizing design systems for scalable and consistent design implementation.

• Hands-on experience using AI tools (e.g., ChatGPT, Claude, Figma AI, Magic Patterns, or similar) for research, ideation, and prototyping.

• Excellent communication and presentation skills, with the ability to clearly articulate design rationale, trade-offs, and vision to diverse audiences.

• Resilience, assertiveness, and a collaborative spirit, with a demonstrated ability to navigate ambiguity and work through conflict constructively.

Preferred Skills:

• Enterprise SaaS experience, particularly within complex or highly regulated domains.

• Specific experience in LegalTech or similar B2B industries within the legal sector.

• Experience designing for workflow-heavy, compliance-driven products that require meticulous attention to detail and process adherence.

• Exposure to AI-first or AI-enhanced product design methodologies and best practices.

• Familiarity with AI/ML product fundamentals and an understanding of how to design for AI-assisted experiences.

📝 Enhancement Note: The experience requirement is framed as 5-7+ years, but the "AI experience level: 5-10" suggests that candidates with up to 10 years of experience are also highly welcome, particularly those with relevant domain or AI experience. The preference for FinTech/LegalTech and regulated industries strongly guides the type of candidate Stretto is seeking.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio demonstrating end-to-end ownership of design projects, from initial concept and research through to high-fidelity execution and impact.

• Showcase strong UX craft, including user journey mapping, interaction design flows, wireframing, prototyping, and visual design execution.

• Highlight meaningful product impact, clearly articulating how your design contributions led to measurable business results or user improvements.

• Include case studies that detail complex problem-solving, strategic decision-making, and your role in driving product strategy.

Process Documentation:

• Present case studies that clearly outline your design process, including user research methodologies, ideation techniques, and validation strategies.

• Detail your approach to collaborating with cross-functional teams, including Product Management and Engineering, throughout the product development lifecycle.

• Showcase your contributions to or experience with design systems, demonstrating an understanding of scalability, consistency, and component-based design.

• If applicable, include examples of how you've used AI tools to augment your design process or contributed to the design of AI-powered features.

• Provide examples of how you define, track, and communicate UX metrics that tie design outcomes to business results.

📝 Enhancement Note: The emphasis on a "Strong portfolio demonstrating end-to-end ownership, UX craft, and meaningful product impact" is paramount. Candidates must be prepared to articulate their process, rationale, and the measurable outcomes of their design work. Explicit mention of AI tools in the portfolio is highly encouraged.

💵 Compensation & Benefits

Salary Range: $130,000 - $150,000 per year.

Explanation of Range: This range is based on the provided salary data for the Sr. Product Designer role in the US. It reflects typical compensation for a mid-senior level designer with 5-7+ years of experience, considering the advanced skill set required, including AI tool proficiency and complex B2B/B2C product design experience within a regulated industry. Market data for similar roles in the United States generally falls within this bracket, with adjustments for location, specific experience, and company size.

Benefits:

• Competitive and comprehensive benefits package.

• Opportunities for professional growth and career advancement within a dynamic organization.

Working Hours: The standard working hours are typically 40 hours per week, aligning with full-time employment expectations. While remote work is supported, candidates should be prepared to dedicate the necessary time to fulfill job responsibilities, which may occasionally extend beyond standard hours for critical project deadlines or urgent stakeholder needs.

📝 Enhancement Note: The salary range is explicitly provided. The benefits are described as "competitive and comprehensive," with "opportunities for growth." The working hours are stated as 40 hours/week, typical for full-time roles, with an implicit understanding of potential flexibility required for a senior role.

🎯 Team & Company Context

🏢 Company Culture

Industry: Stretto operates at the intersection of LegalTech, FinTech, and Case Management services, specifically focusing on the bankruptcy ecosystem. They leverage deep industry expertise and market insights to facilitate case and cash management for corporate restructuring and consumer bankruptcy clients. This specialized niche requires a nuanced understanding of legal processes, financial regulations, and the needs of fiduciaries and legal professionals.

Company Size: Stretto, Inc. is a growing company. While the exact size isn't specified, the context of driving product design across a company's ecosystem and impacting core business outcomes suggests a company with established operations and a commitment to product development, likely in the mid-size to large enterprise category.

Founded: Stretto was founded to provide a full spectrum of case management services, depository solutions, loan modification services, and technology tools. While the founding date is not provided, their established presence in the bankruptcy ecosystem implies a history of service and adaptation to market needs.

Team Structure: The Product Design team is a key strategic function within Stretto, driving design and UX strategy across the company's product ecosystem. This team works closely with Product Management and Engineering leadership, indicating a collaborative, cross-functional structure. The Sr. Product Designer will be an individual contributor, expected to lead design efforts and influence product direction, suggesting a flat or matrixed team structure where expertise is highly valued.

Methodology: The design team emphasizes a user-centric approach grounded in business impact. This involves conducting qualitative and quantitative research, planning and facilitating workshops for ideation and alignment, and delivering end-to-end design solutions. The integration of AI tools and the focus on AI-powered experiences suggest a methodology that embraces emerging technologies to enhance efficiency and innovation. A strong emphasis is placed on defining and tracking UX metrics to demonstrate business value.

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

📝 Enhancement Note: Stretto's focus on the bankruptcy ecosystem is a critical differentiator. Candidates should research this industry to understand the user base (attorneys, paralegals, debtors) and the regulatory environment. The company's emphasis on technology and innovation, particularly with AI, indicates a modern approach to serving a traditional sector.

📈 Career & Growth Analysis

Operations Career Level: This role is classified as a Sr. Product Designer, representing a mid-to-senior level position within the product design discipline. It requires a minimum of 5-7+ years of experience and emphasizes leadership in design execution, strategic influence, and cross-functional collaboration. The role is designed for an individual contributor who can operate with a high degree of ownership and autonomy, shaping product outcomes.

Reporting Structure: The Sr. Product Designer will likely report to a Head of Product Design, Design Manager, or a senior Product leader. They will work closely with Product Managers and Engineering leadership, indicating a collaborative reporting dynamic where cross-functional alignment is key.

Operations Impact: The Sr. Product Designer's work directly impacts core business outcomes by enhancing the efficiency and effectiveness of Stretto's cloud-based B2B and B2C products. By improving user experience for legal professionals and clients, the designer contributes to client retention, operational efficiency for users, and potentially the adoption of new Stretto services. The role is also expected to define and track UX metrics that demonstrably tie design outcomes to measurable business results, highlighting a focus on ROI and strategic contribution.

Growth Opportunities:

• Skill Advancement: Opportunities to deepen expertise in complex B2B/B2C design, regulated industries (LegalTech, FinTech), and cutting-edge AI-driven product experiences.

• Design System Leadership: Contribute significantly to the Stretto Design System, potentially leading its evolution and adoption across product teams.

• Strategic Influence: Grow influence within the organization by shaping product roadmaps, driving design strategy, and mentoring junior designers.

• Cross-functional Leadership: Develop stronger leadership capabilities through extensive collaboration with Product, Engineering, and business stakeholders.

• Industry Specialization: Become a recognized expert in designing for the unique challenges and opportunities within the bankruptcy and legal services ecosystem.

📝 Enhancement Note: The Sr. Product Designer role is a significant step for an individual contributor, offering substantial impact and growth potential. The emphasis on AI and complex B2B/B2C design points towards specialized career development within these high-demand areas.

🌐 Work Environment

Office Type: While the job posting indicates remote work is an option for US-based candidates, Stretto also has physical locations. The work environment likely supports a hybrid model or fully remote engagement, depending on team needs and individual arrangements. The emphasis on collaboration through workshops suggests a need for structured virtual or in-person interaction.

Office Location(s): The company is based in the US, with specific office locations not detailed in the provided information. However, remote candidates in the United States are preferred, indicating a focus on domestic operations and compliance.

Workspace Context:

• A collaborative environment where designers work closely with Product Managers, Engineers, and other stakeholders to deliver integrated solutions.

• Access to modern design tools, including AI-powered applications, to streamline workflows and enhance creative output.

• Opportunities for deep engagement with users and stakeholders to understand complex workflows and business needs within the bankruptcy and legal sectors.

• A culture that values design thinking, user advocacy, and data-driven decision-making.

Work Schedule: The standard work schedule is 40 hours per week for full-time employees. Given the senior nature of the role and the remote work option, there is likely an expectation of flexibility to meet project deadlines and accommodate cross-functional team collaboration across different time zones within the US.

📝 Enhancement Note: The remote-friendly nature for US-based candidates is a key aspect of the work environment. The collaborative culture is emphasized, requiring effective remote communication and engagement strategies.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio to assess experience, skills, and alignment with the role's requirements.

• Portfolio Presentation: A dedicated session where you will present your portfolio, walking through key projects, your design process, rationale, and the impact of your work. This is a critical step to assess your craft, communication, and strategic thinking.

• Cross-functional Interviews: Discussions with Product Management, Engineering, and potentially other stakeholders to evaluate collaboration style, problem-solving abilities, and understanding of business/technical constraints.

• Design Challenge (Potential): You may be asked to complete a design exercise or case study, either as a take-home assignment or a live working session, to assess your approach to a specific design problem relevant to Stretto's products.

• Final Interview: A discussion with senior leadership to assess cultural fit, long-term vision, and overall suitability for the Sr. Product Designer role.

Portfolio Review Tips:

• Curate Strategically: Select 3-5 of your strongest projects that best showcase end-to-end ownership, complex problem-solving, and significant product impact. Prioritize projects relevant to B2B software, data-heavy interfaces, or regulated industries.

• Tell a Story: For each project, clearly articulate the problem statement, your role, the design process (research, ideation, iteration, validation), key decisions and rationale, and the quantifiable outcomes or impact.

• Highlight Process & Rationale: Don't just show final designs; explain why you made certain choices. Demonstrate your strategic thinking and how you balanced user needs with business and technical constraints.

• Showcase AI Integration: If you have experience using AI tools in your design workflow or designing AI-powered features, highlight these projects and explain the benefits and challenges.

• Data & Metrics: Where possible, quantify the impact of your designs. Use UX metrics, business KPIs, or user feedback to demonstrate success.

• Prepare for Questions: Be ready to discuss trade-offs, challenges faced, how you handled stakeholder disagreements, and your approach to accessibility and design systems.

Challenge Preparation:

• Understand the Domain: Research Stretto, the bankruptcy industry, and common challenges faced by legal professionals and their clients.

• Focus on Process: For any design challenge, emphasize your thought process, how you break down problems, and your iterative approach.

• Communicate Clearly: Practice articulating your ideas concisely and persuasively.

• Consider Constraints: Be mindful of potential business, technical, and regulatory constraints in your proposed solutions.

📝 Enhancement Note: The interview process places a heavy emphasis on the portfolio presentation. Candidates must be prepared to articulate their process, rationale, and impact effectively. The mention of AI tools in the context of portfolio presentation suggests looking for evidence of their practical application.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (highly probable given AI integrations and industry standard), Sketch, Adobe Creative Suite (Illustrator, Photoshop).

• AI Tools: ChatGPT, Claude, Figma AI, Magic Patterns, or similar AI platforms for research, ideation, content generation, and prototyping assistance.

• Collaboration & Project Management: Jira, Confluence, Asana, Trello (for tracking design tasks and collaborating with development teams).

Analytics & Reporting:

• UX Analytics: Tools for tracking user behavior and engagement (e.g., Amplitude, Mixpanel, Pendo) to define and measure UX metrics.

• Data Visualization: Tableau, Power BI, or similar tools for understanding data trends and presenting findings.

• Reporting Dashboards: Ability to create and interpret dashboards to communicate design impact and business results.

CRM & Automation:

• While not directly a designer's primary tool, familiarity with CRMs (like Salesforce) and automation platforms can provide context for B2B product design, understanding lead management, customer journeys, and sales processes.

• Integration Tools: Understanding how different systems connect can be beneficial for designing cohesive user experiences across platforms.

📝 Enhancement Note: The explicit mention of AI tools is a key differentiator. Candidates should be prepared to discuss their experience with these tools and how they integrate them into their workflow. Figma is a strong assumption for the primary design tool due to its widespread adoption and AI plugin ecosystem.

👥 Team Culture & Values

Operations Values:

• User-Centricity with Business Acumen: A deep commitment to understanding and advocating for users, balanced with a strong awareness of business objectives, regulatory requirements, and technical feasibility.

• Data-Driven Decision Making: Utilizing qualitative and quantitative data, including UX metrics, to inform design strategy, validate solutions, and measure impact.

• Collaboration and Communication: Fostering open communication and active collaboration with cross-functional teams (Product, Engineering, SMEs, Sales, CSMs) to achieve shared goals.

• Craftsmanship and Quality: A dedication to delivering high-quality, well-executed designs that are efficient, intuitive, and visually polished.

• Innovation and Adaptability: Embracing new technologies, methodologies, and continuous learning to drive product innovation and stay ahead of industry trends, particularly with AI.

Collaboration Style:

• Cross-functional Integration: Designers are expected to be embedded within product teams, working closely with Product Managers and Engineers throughout the product lifecycle.

• Workshop Facilitation: Proactive engagement in planning and leading workshops to drive alignment, discovery, and ideation across diverse teams.

• Constructive Feedback Culture: A willingness to both provide and receive constructive feedback among peers and cross-functional colleagues to elevate design quality and team performance.

• Shared Ownership: A collaborative approach where success is a team effort, with designers contributing to and supporting the overall product vision.

📝 Enhancement Note: The culture emphasizes a blend of user advocacy and business pragmatism, underpinned by data and collaboration. The proactive use of AI tools suggests an innovative and forward-thinking team environment.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating Complex Stakeholder Environments: Effectively managing diverse stakeholder needs and perspectives, including executives, SMEs, clients, and internal teams, while driving design consensus.

• Balancing Constraints: Adeptly balancing user needs with critical regulatory, legal, technical, and business constraints inherent in the bankruptcy and FinTech/LegalTech sectors.

• Designing for Data-Heavy Interfaces: Creating intuitive and efficient user experiences for complex, data-intensive applications used by professionals.

• Integrating AI Seamlessly: Designing effective and ethical AI-powered product experiences that genuinely enhance user workflows and deliver value, rather than being mere additions.

• Driving Design Maturity: Continuing to advocate for and evolve design thinking and best practices within a growing organization, especially in a specialized industry.

Learning & Development Opportunities:

• Specialized Domain Expertise: Deepen knowledge in LegalTech, FinTech, and the intricacies of the bankruptcy process, becoming a subject matter expert in design for this domain.

• AI in Design: Gain advanced practical experience with AI tools and methodologies for product design, positioning yourself at the forefront of this evolving field.

• Design System Leadership: Contribute to and potentially lead the development and expansion of Stretto's design system, enhancing skills in scalability and consistency.

• Strategic Product Influence: Develop stronger strategic thinking and leadership by influencing product roadmaps and contributing to high-level product direction.

• Mentorship: Opportunities to mentor junior designers and contribute to a thriving design community within Stretto.

📝 Enhancement Note: The challenges are rooted in the complexity of the industry and the role's senior responsibilities. Growth opportunities are geared towards specialization in high-demand areas like AI and regulated industries, as well as leadership development.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to influence a product roadmap or strategic direction. What was your approach and the outcome?" (Focus on your ability to use design insights and data to drive strategic decisions.)

• "Walk me through a complex B2B product you designed. What were the key challenges, your design process, and how did you measure its success?" (Be ready to showcase your end-to-end ownership and impact, ideally with data.)

• "How have you used AI tools in your design process? Provide a specific example of how AI helped you solve a design problem or improve efficiency." (Prepare to discuss practical applications of AI in your workflow.)

• "Imagine you're designing an AI-powered feature for bankruptcy petition preparation. What are the key user needs and ethical considerations you'd prioritize?" (Demonstrate your understanding of AI design principles and user-centricity.)

Company & Culture Questions:

• "What interests you about Stretto and the legal/bankruptcy industry specifically?" (Research Stretto's mission, values, and market position. Show genuine interest in the domain.)

• "How do you approach collaboration with Product Managers and Engineers? Describe your ideal working relationship." (Emphasize your cross-functional collaboration skills and proactive communication.)

• "How do you ensure accessibility and inclusivity in your designs?" (Showcase your knowledge of accessibility standards and best practices.)

Portfolio Presentation Strategy:

• Structure is Key: Have a clear narrative for each project: Problem -> Your Role -> Process -> Solution -> Impact/Outcome.

• Focus on "Why": For every design decision, explain the rationale behind it, referencing user research, business goals, or technical constraints.

• Quantify Impact: Use metrics, user feedback, or business results to demonstrate the value of your contributions.

• Showcase AI: If you have relevant projects, explicitly highlight how AI tools were used and the benefits derived.

• Be Prepared for Deep Dives: Anticipate questions about specific design choices, stakeholder interactions, and challenges faced. Practice your delivery to be concise and engaging.

📝 Enhancement Note: The interview preparation heavily emphasizes demonstrating strategic thinking, practical application of AI tools, and the ability to articulate impact. Candidates must be ready to showcase their portfolio with a clear narrative and strong rationale.

📌 Application Steps

To apply for this Sr. Product Designer position:

• Submit your application through the provided application link on the Dayforce platform.

• Tailor Your Resume: Optimize your resume to highlight your 5-7+ years of experience in product design, UX strategy, and specifically your work on complex B2B/B2C software, data-heavy interfaces, and any experience with FinTech, LegalTech, or regulated industries.

• Curate Your Portfolio: Select 3-5 of your strongest projects that best demonstrate end-to-end ownership, UX craft, and measurable product impact. Ensure your portfolio clearly showcases your design process, rationale, and any use of AI tools or AI-assisted design experiences.

• Prepare Your Portfolio Presentation: Practice walking through your selected case studies, focusing on clearly explaining the problem, your process, key decisions, and the outcomes achieved. Be ready to discuss your experience with AI tools and how they enhance your workflow.

• Research Stretto: Understand Stretto's mission, their role in the bankruptcy ecosystem, and their commitment to technology and innovation. This will help you articulate your interest and align your experience with their business goals during interviews.

• Anticipate Technical & Behavioral Questions: Prepare to discuss your design process, stakeholder management skills, and how you approach complex challenges, especially those involving data-heavy interfaces and AI integration.

⚠️ 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.