Lead Insurance Systems Architect

Understory, Inc.•Madison, WI

3d•Hybrid

About The Position

Understory is looking for an Insurance Systems Lead to own the design, specification, and evolution of our policy administration systems. This role sits at the center of underwriting, actuarial, reporting, and technology, and is responsible for ensuring our systems behave correctly across the full policy lifecycle - not just at issuance, but months or years later when audits, bordereaux, and financial reconciliation occur. This role operates at the intersection of deep insurance expertise and hands-on system delivery. You will be expected to think rigorously about insurance mechanics, express them clearly in specifications, actively partner with engineers through implementation, and use modern tooling to accelerate analysis and documentation without compromising correctness. This is not a general product role. It is a systems leadership role for someone who understands property & casualty insurance deeply and can translate that understanding into durable, auditable software behavior.

Requirements

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.

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.