Staff User Experience Designer

Staff User Experience Designer

We're hiring a Staff User Experience Designer 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 operate as a player coach and a mentor, working alongside a team of 2-3 Product Designers while remaining deeply hands-on. This role may grow into formal people management over time, but the immediate focus is hands-on design leadership and mentorship. 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

Support the Growth of the Design Team

• Act as a coach and mentor for more junior Product Designers
• Provide direct feedback and clear creative direction to keep work moving and maintain quality.
• 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 as a lead/senior designer
• Experience establishing or improving design processes on a team.
• 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
• Experience working in regulated markets, especially fintech, capital markets, or private venture strongly preferred.
• 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

Sydecar's Values

Our values are important to the way we live and work at Sydecar. They guide our priorities, behaviors and interactions.

Be Committed

As a team, we rise to meet challenges and recognize that we become stronger and develop character when facing adversity.

Be Excellent

We measure our success not just by what we achieve, but by how we achieve it—through integrity, creativity, elegance, and a commitment to continuous improvement. Excellence is not just doing things well—it's looking for ways to do them better.

Be Humble

Humility is our key to personal and professional growth. We appreciate that great ideas can come from anywhere, regardless of seniority, pedigree, or experience. We care more about collective outcomes than who gets credit or who does what. We try to not let our ego cloud our judgment.

Win Together

Winning is no accident. It is the result of collective hard work, perseverance, sacrifice, and most of all, loving what we do. Winning requires that we give extra—sometimes winning calls for late nights or extra effort, and we show up for clients and each other with urgency and heart. While excellence is a journey, winning is a destination.

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.