Understory · 9 hours ago
Lead Insurance Systems Architect
Madison, WI
Full-time
Hybrid
Senior Level, Lead/StaffUnderstory is a leading provider of insurance solutions built for the era of climate change. They are seeking an Insurance Systems Lead to own the design and evolution of policy administration systems, ensuring they behave correctly across the full policy lifecycle while partnering with actuarial and underwriting teams.
AnalyticsArtificial Intelligence (AI)Big DataInsurTech
Responsibilities
Own the design and evolution of Understory’s policy administration systems as core financial and regulatory infrastructure, including evaluating build vs. buy decisions and leading the selection, integration, customization, and long-term ownership of off-the-shelf insurance solutions when appropriate
Ensure policy data supports accurate loss ratio measurement, carrier reporting, bordereaux, reserves, and reinsurance analysis
Design system workflows that correctly handle endorsements, mid-term changes, cancellations, renewals, reinstatements, and historical policy reconstruction
Anticipate and resolve edge cases that surface downstream through audits, reporting discrepancies, or financial close
Partner directly with actuarial and underwriting teams to translate risk and pricing considerations into system behavior
Work closely with software engineers to break down complex insurance problems into buildable, testable components
Provide technical and domain leadership to engineers to ensure implementations align with insurance reality, not just clean abstractions
Ensure systems are designed with auditability, traceability, and long-term correctness in mind
Qualification
Required
Have deep experience with property & casualty insurance systems and policy lifecycles across multiple products
Understand how policy data, pricing, and endorsements flow through filings, reporting, reserves, and reinsurance
Have worked closely with actuaries and underwriters and are comfortable discussing loss ratio drivers, pricing mechanics, and risk tradeoffs
Have implemented or integrated off-the-shelf insurance or policy administration systems and have lived through the downstream audits, bordereaux reconciliation, or reporting corrections that reveal where those systems succeed and where they fall short
Have experience onboarding new carriers or insurance partners and can speak fluently to their system, reporting, and data expectations
Have moved quickly to support new insurance products while maintaining system integrity and regulatory correctness
Can write clear, unambiguous specifications that engineers trust and enjoy building from
Are comfortable leading and guiding software engineers through complex, insurance-driven system design decisions
Are pragmatic, opinionated, and comfortable operating in a fast-moving startup environment
Have used modern technical tools, including AI, to efficiently specify and evolve insurance systems while keeping the focus on insurance behavior and correctness
Benefits
Full-time benefits
Company
Understory
Understory is an insurance company that develops smart weather station micro-grids.
Founded in 2012
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$57.84MKey Investors
True Ventures4490 Ventures
2024-06-05Series A· $15M
2023-06-06Series Unknown· $13.13M
2020-05-22Series B· $7.5M
Leadership Team
Alex Kubicek
Chief Executive Officer and Co-founder
Bryan Dow
Co-founder
Recent News
globallegalchronicle.com
2025-09-26
2025-09-17
Company data provided by crunchbase