Product Designer II, Agent Experience

Bestow is a vertical technology platform modernizing the life insurance industry through infrastructure, AI, and automation. The Product Designer II will own end-to-end design execution for Agent Experience initiatives, conducting research, shaping solutions, creating prototypes, and partnering with product, engineering, and external stakeholders to deliver clear and credible workflows for agents, wholesalers, and back-office teams.

Responsibilities:

• Own end-to-end design for assigned initiatives — from problem framing and research through prototyping, validation, and implementation partnership
• Design for multiple distinct user types in one system — independent agents, wholesalers, and internal back-office teams — including role-based permissions and data import workflows
• Conduct and synthesize research through user interviews, usability testing, and data analysis, including moderated sessions with external agents
• 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, engineering, and external partners
• Navigate and collaborate in shared code repositories — reading existing prototypes, iterating in an IDE with AI assistance, and partnering with engineers during implementation
• Design integration experiences where the product surface is partly determined by a partner’s system — single sign-on, pre-fill, status, and quoting APIs
• 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, accuracy, and compliance matter as much as polish

Requirements:

• 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
• Comfortable presenting work to stakeholders and holding a point of view in the room
• 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
• Ability to operate in ambiguity and making progress with incomplete information
• Works well inside a shared design direction — gives and receives critique proactively, and treats a senior partner as leverage rather than oversight
• Strong preference: 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 designing for professional or agent-facing channels (brokerage, wealth, distribution, marketplace supply side)
• Background designing experiences that span two companies' brands
• Experience with quoting, pricing, illustration, or configurator interfaces
• Experience with agentic or multi-step AI workflows in design or product exploration
• Familiarity with design-system-to-code pipelines (Figma to production components)