(Senior) UX/UI Product Designer

At Coventry, the market leader in life settlements, we’re reinventing how life insurance and annuities are built, distributed, and experienced — and we’re hiring a UX/UI Product Designer to help design our AI-native platform for consumers and the businesses that serve them.

In this role, you’ll own the design of both internal business operations & consumer user experiences in close collaboration with product and engineering. We’re looking for somebody comfortable working on tools and first-party interfaces as well as developing front-end UX for external users in the life insurance, annuities, and personal medical data spaces.

We’re looking for someone energized by hard design problems, comfortable with AI tools, and motivated to build a design culture where curiosity, craft, and ownership matter. You should have high standards and the flexibility to adapt your process as new tools go from experimental to essential.

This role is in-office two days a week near Madison Square Garden and reports to the VP of Product. You’ll be the first staff designer, which means wide scope, real influence, and room to grow into team leadership if that’s where you want to go. Expect to help educate stakeholders on Design best practices as part of getting started.

In your first six months, you will:

• Own the end-to-end design of core users journeys — both employee tooling use-cases and external customer interfaces and product surfaces — producing wireframes, mockups, and prototypes that make complex processes intuitive and easy-to-use
• Define and evolve the product surfaces’ information architecture and ontology: the labels, categories, and conceptual models that help both high-skill and first-time users navigate and operate quickly and effectively
• Establish the design foundation for AI-powered features, including how consumers and internal business users interact with intelligent guidance, dynamic recommendations, and agent-driven workflows
• Build and maintain a design system that keeps the experience consistent, accessible, and ready to scale across product surfaces
• Contribute to the product roadmap with user insight and design thinking — and help set the future trajectory of Coventry’s workflows and external surfaces

Requirements

A little about you:

• 3–7 years of product design experience with a strong portfolio of shipped, B2B and B2C-facing work — user research, ontological decisions, wireframes, and live products
• Deep UX fundamentals: information architecture, interaction design, user flows, and the ability to design for users making high-stakes decisions
• Strong UI craft in Figma — typography, visual hierarchy, spacing, and production-ready designs
• Actively using AI and generative AI tools in your design workflow, with a real point of view on how they change the work — not just the speed
• Clear communicator who can present and defend design decisions, take feedback directly, and keep moving in a fast-paced, collaborative environment
• Track record of owning projects end-to-end and delivering against milestones

Extra points:

• Experience in life insurance, fintech, healthtech, or any high-trust consumer product where anxiety and decision complexity are core design problems
• Background in content design, UX writing, or plain language standards in regulated industries
• Early-stage startup experience
• Familiarity with conversion optimization, funnel analysis, or designing with quantitative user data

Benefits

Salary:

The base salary range for this role is USD $130,000.00 to $160,00.00. Actual pay and the Senior aspect of the job title depends on experience, location, and performance. Total compensation also includes eligibility for short- and long-term incentives and equity. Benefits include health insurance, 401(k), free in-office food and drinks, paid holidays, and encouraged PTO.

About Coventry:

Founded in 1982, Coventry created the life settlement market and remains its category leader, helping policyowners unlock value from life insurance policies they no longer need. As part of a broader effort to transform the business, Coventry acquired Leopard in 2025, a B2B insurtech incubated by The D. E. Shaw Group’s venture studio and launched in 2024 to streamline life insurance and annuity lifecycles. Now fully integrated into Coventry’s technology organization, Leopard is part of a unified team advancing Coventry’s long-term ambition to modernize how complex insurance and annu…