PRODUCT MANAGEMENT - Sr Product Designer

Stretto, Inc.

17h

About The Position

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.

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

Nice To Haves

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

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