SageSure · 4 hours ago
Principal Designer
Chicago, IL
Full-time
Hybrid
Lead/StaffSageSure is a leader in catastrophe-exposed property insurance, seeking a Principal Designer to support their Program Experience team. The role involves collaborating with product teams to shape software, drive end-to-end user experiences, and lead design thinking and execution.
Commercial InsuranceFinancial ServicesInsuranceProperty Insurance
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
Qualification
Required
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
Preferred
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
Benefits
Generous health benefits
Tuition reimbursement
Wellness allowance
Paid volunteer time off
A matching 401K plan
Company
SageSure
SageSure offers property and casualty insurance solutions tailored for homeowners in regions prone to natural catastrophes.
Founded in 2009
1001-5000 employees
H1B Sponsorship
SageSure has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (7)
2024 (3)
2023 (4)
2022 (2)
2021 (1)
2020 (2)
Funding
Current Stage
Late StageTotal Funding
$900MKey Investors
Wintrust FinancialAres ManagementCitizens Bank
2025-07-11Debt Financing· $100M
2023-05-16Private Equity· $250M
2023-03-28Debt Financing· $50M
Leadership Team
Terrence McLean
Co-Founder, President, and CEO
C
Colin Smith
Chief Operating Officer
Recent News
Business Wire
2025-12-01
2025-10-03
2025-07-30
Company data provided by crunchbase