Principal Designer

SageSure • Chicago, IL

1d

About The Position

If you're looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a Principal Designer supporting our Program Experience team. We’re looking for a passionate, experienced designer who thrives at the intersection of strategy and craft. If you have a strong background in insurance, insurtech, fintech, or complex business and consumer workflows, and love leading discovery, UX research, and high-impact design—you’ll feel right at home here. In this role, you’ll work hand-in-hand with product teams to shape our flagship software, fuel the growth of a multi-billion-dollar book of business, and drive end-to-end experiences that make a real difference for our users. You’ll help lead design thinking, research, and execution—owning outcomes, not just deliverables. This is your opportunity to help set the bar for what best-in-class looks like in our industry.

Requirements

• Significant experience in a leading design role with the ability to challenge assumptions and bring design thinking into problem solving.
• Facility in working with data heavy but whitespace respecting patterns, and experience discovering, designing, and advocating for meaningful digital customer experiences that meet strategic customer and business needs.
• Keen understanding of marketplaces, logistics, and workflows.
• A proven track record in taking legacy processes and systems and turning them into modern software experiences
• Fluency in creating workflow diagrams, interactive prototypes, and finished designs, with documentation that clearly communicates the design and functionality of new features.
• Experience measuring, reporting on, and advancing the value of new and existing features.
• Strong written and verbal communication skills to explain evidence-based design decisions for review and implementation by teammates.
• Strong attention to detail, including language, patterns, visual design flaws, etc.
• A portfolio that tells a story of problem solving with quality visual designs showcasing your eye for detail; clear and thoughtful writing; thoughtful discovery practices; etc.

Nice To Haves

• Experience in insurance / insurtech or fintech and rich B-to-B-to-C software applications.
• A proven track record advocating for and growing design mindsets and team culture within organizations.
• Proficiency working with a fully remote team or in hybrid work environments.

Responsibilities

• Work with company leaders and your team in building software for experts in bringing our insurance products to life, with modern expectations for clarity, coherence, and usability along with business impact.
• Create and execute designs, both from a blank slate and within an existing system, shaping how design functions inside the company and in our design team.
• Lead discovery, user research, and synthesis, and use metrics to drive success.
• Collaborate with product managers, data scientists, engineers, and other designers and lead design direction and efficient implementation.
• Facilitate conversations on improving product features and our robust design system by articulating tradeoffs while defining final designs.
• Communicate the rationale behind the intentions, decisions, and goals of proposed design solutions while incorporating constructive feedback through design iterations.

Benefits

• SageSure offers generous health benefits and perks, including tuition reimbursement, wellness allowance, paid volunteer time off, a matching 401K plan, and more.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees