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.

We’re looking for a designer who combines strong research instincts with the ability to shape and ship ideas quickly. The most meaningful work on this team happens where ambiguity is high: discovery starts before requirements are fully baked, and the best designers here don’t wait for a finished PRD — they help define the problem, test direction, and bring partners along with evidence.

This team is prototype-first. You’ll work in Figma and in coded prototypes — often in shared repos alongside engineering and product — using AI tooling to move faster without sacrificing judgment. If you’re energized by the shift from static handoffs to living prototypes, and you can speak concretely to how you’ve adapted your workflow between canvas and code, you’ll thrive here.

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

Required: 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

Required: 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
Have experience with agentic or multi-step AI workflows in design or product exploration

Are familiar with design-system-to-code pipelines (Figma → production components)

Have a background designing internal tools, ops platforms, or data-heavy workbench experiences

Have exposure to AI-assisted product features (copilots, intelligent document review, workflow automation)