PRODUCT MANAGEMENT - Sr Product Designer

Summary

Stretto delivers a full spectrum of case management services, depository solutions, loan modification services, and technology tools to fiduciaries and legal professionals. Sitting at the center of the bankruptcy ecosystem, Stretto leverages deep industry expertise and market insights to facilitate every aspect of case and cash management for its corporate-restructuring and consumer-bankruptcy clients, as well as fiduciaries and other industry professionals.

The Product Design team at Stretto drives product design and UX strategy across the company’s product ecosystem, directly impacting core business outcomes. The team is focused on delivering high-quality, efficiency-driven solutions to law practices across the country.

We are seeking a Sr. Product Designer to lead design across a suite of complex, cloud-based B2B and B2C products used by attorneys, paralegals, and debtors to prepare bankruptcy petitions and manage cases. This is a senior individual contributor role for a designer who brings strong craft, sound judgment, and the maturity to collaborate effectively with cross-functional teams and at times challenging stakeholders.

The Sr. Product Designer is expected to deliver high-quality design execution, contribute to product direction, and champion design thinking within the organization. This role is responsible for defining and articulating user and product needs and making a meaningful impact across Stretto’s product portfolio.

Essential Duties and Responsibilities

• Lead design efforts across assigned product areas with a high degree of ownership and craft
• Partner with Product and Engineering leadership to influence roadmap, prioritization, and product direction
• Navigate complex stakeholder environments—including executives, SMEs, CSMs, clients, Product, and Engineering— communicating design rationale clearly and driving toward alignment
• Identify and drive short- and long-term product and UX improvements grounded in user needs and business impact
• Define, track, and communicate UX metrics that tie design outcomes to measurable business results
• Collaborate cross-functionally throughout the product lifecycle, from discovery through delivery
• Plan and facilitate workshops for alignment, discovery, and ideation
• Conduct and synthesize qualitative and quantitative research to inform strategy and validate solutions
• Deliver end-to-end design solutions, from concept to high-fidelity execution (journeys, flows, wireframes, prototypes)
• Leverage AI tools to accelerate workflows across research, ideation, content, and prototyping
• Contribute to the design and definition of AI-powered product experiences in collaboration with Product and Engineering
• Contribute to and evolve the Stretto Design System and design best practices
• Provide constructive feedback to peers and support a collaborative design culture
• Advocate for users while balancing regulatory, technical, and business constraints
• Contribute to scoping, planning, and estimation of design efforts
• Perform other duties as assigned

Education and/or Work Experience Requirements

• 5–7\+ years of experience in product design, UX, or interaction design
• Experience designing complex B2B software products: FinTech or similarly regulated industries a plus
• Ability to connect design decisions to business goals and make sound, well-reasoned trade-offs
• Comfortable working with and influencing cross-functional stakeholders through clear communication and strong design rationale
• Experience working with complex, data-heavy interfaces and large-scale information systems
• Solid competency across the full UX spectrum: research, IA, interaction design, prototyping, visual design, and design strategy
• Knowledge of accessibility, design systems, and scalable design practices
• Familiarity with AI/ML product fundamentals: exposure to designing AI-assisted experiences is a plus
• Hands-on experience using AI tools (e.g., ChatGPT, Claude, Figma AI, Magic Patterns, or similar) for research, ideation, and prototyping
• Excellent communication skills, with the ability to clearly articulate rationale, trade-offs, and vision to diverse audiences
• Resilient, assertive, and collaborative—comfortable navigating ambiguity and working through conflict constructively
• Strong portfolio demonstrating end-to-end ownership, UX craft, and meaningful product impact
• Bachelor’s degree in Interaction Design, HCI, Graphic Design, or related discipline, or equivalent experience (master’s preferred)
• Formal portfolio presentation required during the interview

Preferred Qualifications

• Enterprise SaaS experience, in complex or regulated domains
• Experience in FinTech, LegalTech, or similar B2B industries
• Experience designing for workflow-heavy, compliance-driven products
• Exposure to AI-first or AI-enhanced product design

Physical Requirements

1\. Ability to safely and successfully perform the essential job functions consistent with federal, state, and local standards.

2\. Might be exposed to prolonged sedentary hours of work and use of computer.

3\. Ability to travel domestically and/or internationally as needed to fulfill job responsibilities. Travel may involve air, train, automobile, or other modes of transportation.

Why Join Stretto?

At Stretto, you’ll be part of a collaborative team that’s dedicated to innovation, excellence, and growth. You’ll have the opportunity to shape the direction of a rapidly expanding business unit while making a direct impact on the legal community.

The Company’s salary ranges are determined by role, level, location and alignment with market data. Individual pay is determined through interviews and an assessment of various factors, including job-related skills, relevant education and experience, abilities of the applicant, and equity with other team members. The salary range listed here is subject to change at any time, at the Company’s discretion, and does not alter in any way the at-will nature of the employment relationship.

Stretto offers a competitive and comprehensive benefits package, along with opportunities for growth. We are an equal opportunity employer encouraging diversity in the workplace. All qualified applicants will receive consideration for employment without regard to race, national origin, gender, age, religion, disability, sexual orientation, veteran status, marital status or any other characteristics protected by law.