[Hiring] Senior Product Designer @Stretto, Inc.

Role Description

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.

• 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.

Qualifications

• 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.

Requirements

• 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

• Ability to safely and successfully perform the essential job functions consistent with federal, state, and local standards.
• Might be exposed to prolonged sedentary hours of work and use of computer.
• Ability to travel domestically and/or internationally as needed to fulfill job responsibilities. Travel may involve air, train, automobile, or other modes of transportation.

Benefits

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.