Director, User Experience & Design

About the Role We’re hiring a Director of User Experience & Design to help redefine our product experience as we scale. This is a high‑ownership, high‑execution role for a design leader who moves fast, makes strong decisions, and drives work to completion while maintaining an exceptional bar for craft and customer understanding. You’ll manage a team of Product Designers while remaining deeply hands‑on. You’ll play a central role in shaping product strategy through deep user research, strong design judgment, and close partnership with Product and Engineering. Our product operates in a regulated environment, serving a broad range of customers from first time investors and deal organizers to large venture capital firms. Success in this role requires balancing compliance and regulatory constraints with delivering a best‑in‑class, intuitive experience for complex financial workflows. What You’ll Do Own and Evolve the End‑to‑End UX Lead the evolution of the entire user experience for deal leads, investors, and internal operations teams Personally drive design on high‑impact initiatives, from discovery through delivery Simplify complex, regulated workflows into clear, intuitive, and experiences that create trust for our customers Set and maintain a high bar for design quality while operating with startup speed Research‑Led Design Leadership Lead user research as a first‑class input to product strategy and design decisions Partner closely with Product Managers to define problems, test assumptions, and validate solutions Act as a strong voice of the customer in roadmap and prioritization discussions as well as on specific initiatives Synthesize qualitative and quantitative insights into clear, actionable direction Design Systems & UI Foundations Lead the adoption and evolution of design systems, shared UI components, and design libraries Partner with Engineering and Product to ensure consistent implementation across the product Define standards, guidelines, and best practices that enable speed without sacrificing quality Balance systemization with flexibility as the product evolves Design for Impact in a Regulated Environment Work with SMEs to balance regulatory, compliance, and operational requirements with excellent UX Design systems and flows that support trust, accuracy, and clarity for investors and deal organizers Make confident tradeoffs when constrained, and communicate them clearly Use data to inform decisions and optimize for outcomes such as conversion, activation, and retention Build and Lead a High‑Ownership Team Manage, mentor, and develop a team of Product Designers Provide direct feedback and clear direction to keep work moving forward Foster a culture of trust, collaboration, speed, accountability, and continuous improvement Help designers grow both their craft and product thinking What We’re Looking For 7+ years of product design experience, including at least 2 years experience leading or managing designers Strong demonstration in building design teams and scalable design processes Exceptionally strong hands‑on design skills, with a portfolio demonstrating end‑to‑end UX ownership and redesigns Deep experience leading and applying user research to drive strategy and execution Strong experience designing complex workflows, multi‑step processes, or system‑heavy products Strong experience in design systems and UI libraries Strong preference for experience working in regulated markets, especially fintech, capital markets, or private venture Ability to balance compliance and regulatory needs with delivering a best‑in‑class customer experience Experience with consumer and/or SMB products strongly preferred Data‑informed, outcome‑oriented designer with a bias toward execution Comfortable operating in ambiguity and energized by early‑stage environments Equal Employment Opportunity Sydecar is committed to the principle of equal employment opportunity for all employees and to providing employees with a work environment free of discrimination and harassment. All employment decisions at Sydecar are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, national, social or ethnic origin, sex (including pregnancy), age, physical, mental or sensory disability, HIV Status, sexual orientation, gender identity and/or expression, marital, civil union or domestic partnership status, past or present military service, family medical history or genetic information, family or parental status, or any other status protected by the laws or regulations in the locations where we operate. Sydecar will not tolerate discrimination or harassment based on any of these characteristics. Sydecar encourages applicants of all ages. #J-18808-Ljbffr