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This position was posted on February 10, 2026 and is likely no longer accepting applications. We've kept it here for historical reference. Check out the similar jobs below!

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Controller

Job Overview

Location

Chicago

Job Type

Full-time

Category

Accounting

Date Posted

February 10, 2026

Full Job Description

đź“‹ Description

  • • Corgi is revolutionizing the insurance industry as the first full-stack, AI-native carrier specifically designed for the dynamic needs of startups. We offer a suite of modular coverages, including Directors & Officers (D&O), Technology & AI Errors & Omissions (E&O), Cyber, Commercial General Liability (CGL), Homeowners & Non-Owned Automobile (HNOA), Fiduciary, and specialized AI Liability. Our unique approach leverages our own balance sheet for underwriting and an advanced AI-driven platform to provide instant quotes, adaptive coverage, and compute-speed underwriting and claims processing, catering to the fast-paced, venture-backed startup ecosystem.
  • • As the Controller at Corgi, you will be entrusted with the critical responsibility of overseeing all accounting operations, financial reporting, and internal controls for our full-stack carrier and associated entities. This role operates within a highly regulated and rapidly evolving environment, demanding meticulous attention to detail and a proactive approach. Reporting directly to the Head of Business, you will be the linchpin ensuring the accuracy, completeness, and timeliness of our financial information as we experience significant growth in premiums, product offerings, and geographical reach.
  • • You will collaborate closely with the Head of Business and the founding team to translate Corgi's innovative AI-native operations and modular product portfolio into transparent, auditable financial statements and insightful, actionable financial analysis. Your expertise will be crucial in bridging the gap between our cutting-edge technology and robust financial management.
  • • Key responsibilities encompass leading all day-to-day accounting functions, including General Ledger (GL), Accounts Payable (AP), Accounts Receivable (AR), cash management, payroll, and fixed asset accounting for Corgi's insurance, reinsurance, and service entities. You will own the critical month-end and year-end closing processes, delivering precise and timely Generally Accepted Accounting Principles (GAAP) financial statements (Profit & Loss, Balance Sheet, Cash Flow) alongside comprehensive management reporting.
  • • A significant aspect of this role involves managing specialized insurance accounting. This includes accurately accounting for written and earned premiums, maintaining unearned premium reserves, tracking loss and Loss Adjustment Expense (LAE) reserves, overseeing reinsurance activities (both ceded and assumed), managing commissions, and accounting for deferred acquisition costs. Your deep understanding of these insurance-specific financial elements will be paramount.
  • • You will play a vital role in supporting statutory and regulatory reporting requirements for our full-stack carrier and any captive or reinsurance structures. This includes preparing and submitting state filings and actively participating in regulatory examinations, ensuring Corgi remains compliant with all relevant insurance regulations.
  • • Designing, implementing, and maintaining robust internal controls, comprehensive accounting policies, and efficient procedures will be a core function. These systems must be tailored to the unique demands of an AI-driven, high-growth insurance carrier, ensuring scalability and integrity.
  • • As the primary internal point of contact for external audits and tax compliance, you will be responsible for preparing detailed workpapers and coordinating seamlessly with auditors and tax advisors, streamlining these critical processes.
  • • You will partner closely with the Head of Business on budgeting, forecasting, and variance analysis. This involves providing deep insights into key performance indicators such as loss ratios, acquisition costs, and unit economics, segmented by product and customer cohort, enabling strategic decision-making.
  • • Managing cash flow forecasting, assessing capital needs, and overseeing treasury operations, including maintaining strong bank relationships and addressing any regulatory capital requirements, will be essential for financial stability.
  • • A key initiative will be evaluating and implementing our Enterprise Resource Planning (ERP) accounting stack. You will drive the integration of our accounting systems with Corgi's AI-native insurance platform, automating data flows from underwriting, policy administration, and claims into our financial systems, thereby enhancing efficiency and accuracy.
  • • Over time, you will have the opportunity to build and lead a high-performing accounting team, establishing rigorous standards for accuracy, responsiveness, and ownership, fostering a culture of excellence.
  • • This role offers a unique opportunity to shape the financial foundation of a groundbreaking insurtech company, contributing directly to its growth and success in a fast-paced, innovative environment.

Skills & Technologies

Onsite
Degree Required

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About Corgi

Corgi is a company focused on providing innovative solutions in the [industry/sector]. They specialize in [key products/services] designed to [solve specific problems or meet customer needs]. With a commitment to [company values like quality, customer satisfaction, or technological advancement], Corgi aims to [company's overarching goal or mission]. Their offerings cater to [target audience or market segment], enabling them to [achieve specific benefits]. The company leverages [technology or methodology] to deliver efficient and effective results for its clients. Corgi strives to be a leader in its field by continuously [mention areas of focus like research, development, or customer support].

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