Product Designer II

About the role

Bestow is seeking a Product Designer II to join our Underwriting module's mission of making insurance more accessible and human-centered. You'll own design for key workbench initiatives—turning complex underwriting and manager workflows into experiences that are clear, efficient, and defensible.

What You'll Do

• Own end-to-end design for assigned initiatives—from problem framing and research through prototyping, validation, and implementation partnership
• Conduct and synthesize research through user interviews, usability testing, and data analysis to validate design decisions and inform product strategy
• Shape solutions in partnership with product managers—helping define problems, outline approaches, and establish success criteria when requirements are still forming
• Create user flows, diagrams, Figma designs, and coded prototypes that communicate direction clearly to stakeholders and engineering
• Navigate and collaborate in shared code repositories—reading existing prototypes, iterating in an IDE with AI assistance, and partnering with engineers during implementation
• Partner with engineering to protect design integrity while balancing technical constraints
• Contribute to design critiques and help elevate quality across the team
• Champion user-centered design in a regulated product—where trust, auditability, and operational clarity matter as much as polish

Who You Are

• Bachelor's degree or equivalent experience
• 3–5 years of product design experience, ideally on complex or regulated products (fintech, healthcare, enterprise B2B, insurance, or similar)
• Portfolio demonstrating systems thinking, research-to-shipping discipline, and attention to interaction and visual detail
• Track record of delivering product work with measurable impact—even when the path from research to production isn't linear
• Proficiency in Figma and modern prototyping approaches
• Hands-on experience building or iterating on designs in an IDE or code-based environment (e.g., Cursor, VS Code with AI assistants, Claude Code)—not only watching engineers prototype
• Comfort reading and navigating coded prototypes and collaborating in repos with engineering and product partners
• Strong preference: Demonstrated use of AI in your daily design practice—with specific examples of what you automate, what you keep human, and what failed
• Experience contributing to or working within design systems and component libraries
• Strong analytical skills; comfortable using qualitative and quantitative inputs to inform decisions
• Excellent communication skills and a track record of productive cross-functional partnership
• Comfortable operating in ambiguity and making progress with incomplete information

Preferred, but not required

• Demonstrated use of AI in your daily design practice—with specific examples of what you automate, what you keep human, and what failed
• Experience contributing to or working within design systems and component libraries
• Background designing internal tools, ops platforms, or data-heavy workbench experiences
• Exposure to AI-assisted product features (copilots, intelligent document review, workflow automation)