Cowbell is signaling a new era in cyber insurance by harnessing technology and data to provide small and medium-sized enterprises (SMEs) with advanced warning of cyber risk exposures bundled with cyber insurance coverage adaptable to the threats of today and tomorrow. Championing adaptive insurance, Cowbell follows policyholders’ cyber risk exposures as they evolve through continuous risk assessment and continuous underwriting. In its unique AI-based approach to risk selection and pricing, Cowbell’s underwriting platform, powered by Cowbell Factors, compresses the insurance process from submission to issue to less than 5 minutes. Founded in 2019 and based in the San Francisco Bay Area, Cowbell has rapidly grown, now operating across the U.S., Canada, U.K., and India. This growth was recently bolstered by a successful Series C fundraising round of $60 million from Zurich Insurance. This investment not only underscores the confidence in Cowbell’s mission but also accelerates our capacity to revolutionize cyber insurance on a global scale. With the backing of over 25 prominent reinsurance partners, Cowbell is poised to redefine how SMEs navigate the evolving landscape of cyber threats. Position Overview We are seeking a highly experienced Controller with a strong background in GAAP and statutory accounting principles (SAP), experience with NAIC regulatory requirements, including Managing General Agent (MGA) operations, and revenue recognition. The ideal candidate will have a track record of successfully managing financial reporting, compliance, accounting operations and internal controls across multiple jurisdictions. Key Responsibilities Financial Reporting & Compliance + Oversee the preparation and filing of quarterly and annual statutory financial statements in compliance with NAIC and state insurance department requirements. + Ensure accuracy and timeliness of GAAP and statutory financial reporting, including footnote disclosures and management discussion & analysis. + Coordinate with regulatory agencies, external auditors, tax professionals, and examiners to facilitate financial reviews, audits, and examinations. + Maintain up-to-date knowledge of SAP, GAAP, and regulatory changes, ensuring timely adoption of new requirements. Revenue Recognition & MGA Operations + Oversee revenue recognition policies and ensure compliance with ASC 606 (Revenue from Contracts with Customers) and SAP requirements. + Monitor and evaluate premium revenue, commission structures, profit-sharing arrangements, and ceded reinsurance agreements to ensure proper accounting treatment. + Collaborate with carriers and broker to ensure accurate premium reporting, bordereaux reconciliation, and cash settlements. + Develop and implement best practices for recognizing revenue and MGA-related financial transactions. Accounting & Internal Controls + Lead the monthly, quarterly, and year-end close process, ensuring completeness and accuracy of financial records. + Implement and maintain strong internal controls over financial reporting, including reconciliations + Oversee investment accounting, reinsurance accounting, cash management, premium collections and tax compliance Regulatory & Risk Management + Manage risk-based capital (RBC) reporting, statutory capital adequacy calculations, and regulatory submissions. + Oversee statutory reserves, coordinating with actuarial teams to ensure appropriate reserving methodologies. + Ensure compliance with state insurance laws, including maintaining and monitoring statutory deposit requirements and regulatory reporting deadlines. Leadership & Strategic Initiatives + Lead and develop a team of accounting professionals, fostering a culture of continuous improvement and excellence. + Develop and maintain effective relationships with business partners and cross-functional teams at all levels of the enterprise + Develop and maintain relationships with key external stakeholders: auditors, regulators and rating agencies + Partner with Head of Finance, to provide financial insights and strategic recommendations. + Drive improvements in reporting processes, automation, and financial systems to enhance efficiency and accuracy. Qualifications and Experience + CPA with 10+ years of accounting and financial reporting experience in a similar role in the P&C insurance industry, including experience with MGA operations and revenue recognition. + Strong knowledge of NAIC statutory reporting, GAAP, and MGA operations. + Advanced Excel expertise, proficiency in financial systems such as NetSuite, Adaptive, Wings and Ramp preferred + Excellent leadership, analytical, Interpersonal and communication skills with the ability to interact with various management levels + Experience working with state insurance regulators and NAIC examinations. + Knowledge of insurance investments, reinsurance arrangements and MGA financial models. + Strong understanding of data analytics and financial modeling. + Ability to manage multiple tasks and adapt to a dynamic, fast-paced environment What Cowbell brings to the table: + Employee equity plan for all and wealth enablement plan for select customer facing roles + Comprehensive wellness program, meditation app subscriptions, lunch and learn, book club, happy hours and much more + Professional development and the opportunity to learn the ins and outs of cyber insurance, cyber security as well as continuing to build your professional skills in a team environment Equal Employment Opportunity: We are committed to equal opportunity in the terms and conditions of employment for all employees and job applicants without regard to race, color, religion, sex, sexual orientation, age, gender identity or gender expression, national origin, disability, or veteran status. Cowbell is a leading innovator in cyber insurance, dedicated to empowering businesses to always deliver their intended outcomes as the cyber threat landscape evolves. Guided by our core values of TRUE—Transparency, Resiliency, Urgency, and Empowerment—we are on a mission to be the gold standard for businesses to understand, manage, and transfer cyber risk. At Cowbell, we foster a collaborative and dynamic work environment where every employee is empowered to contribute and grow. We pride ourselves on our commitment to transparency and resilience, ensuring that we not only meet but exceed industry standards. We are proud to be an equal opportunity employer, promoting a diverse and inclusive workplace where all voices are heard and valued. Our employees enjoy competitive compensation, comprehensive benefits, and continuous opportunities for professional development. For more information, please visit https://cowbell.insure/.