Join to apply for the Chief Financial Officer role at Oliver James Join to apply for the Chief Financial Officer role at Oliver James We are partnering with a privately held, highly rated specialty insurance group undergoing significant strategic growth. This organization is seeking a transformational finance leader to step into a key role - shaping the future of its financial operations and long-term performance. As the senior-most finance executive, you'll partner with executive leadership to drive financial strategy, capital allocation and reporting excellence.

Role: Chief Financial Officer

Reports To: CEO

Direct Reports: 5

Preferred Work Locations: Chicago, IL

Overview

The Chief Financial Officer (CFO) serves as the principal leader for all financial activities, steering both the strategic direction and day-to-day financial operations. This executive manages a diverse, multi-disciplinary team across reporting, treasury, planning, receivables, premium audits, taxation, and investment accounting. The CFO partners closely with the CEO and senior leadership to develop and implement company-wide initiatives, ensuring optimal deployment of resources.

A key aspect of this role is refining management reporting processes to deliver actionable insights and performance metrics that inform business decisions. The CFO is also responsible for maintaining robust financial controls, ensuring the integrity and timeliness of financial statements, protecting company assets, and promoting prudent fiscal management.

Key Duties

Direct the organization's financial planning, budgeting, and forecasting, enabling business units to set, track, and achieve financial objectives. Prepare and deliver regular and special financial reports and presentations for executive management, the Audit Committee, insurance boards, and the Board of Directors to support oversight and governance. Develop, implement, and monitor effective financial policies throughout the finance function and related business areas. Cultivate a high-performance culture within the finance department through strong leadership and guidance. Build and maintain productive relationships with financial institutions, investment partners, asset custodians, rating agencies (such as A.M. Best), regulators, and other key external stakeholders. Collaborate with actuarial teams to ensure that loss reserves are appropriately conservative and to analyze profitability trends that may require business unit engagement. Supervise investment manager performance and compliance with established investment guidelines. Regularly assess and recommend changes to investment allocations in response to evolving economic conditions. Oversee all aspects of tax planning, compliance, and reporting, working alongside external accountants as needed. Liaise with external auditors to facilitate timely, successful audits and identify opportunities to enhance closing processes and internal controls. Continuously evaluate and strengthen internal controls to ensure compliance with regulatory requirements such as the Model Audit Rule. Perform other responsibilities as assigned.

Skills & Attributes

Advanced expertise in GAAP and statutory accounting, with strong analytical acumen. Exceptional attention to detail. Proven ability to attract, develop, and retain top talent in a results-oriented environment. Skilled at leveraging technology to optimize financial and operational processes. Resilience and composure under pressure, with the flexibility to adapt to shifting priorities and deadlines. Outstanding written and verbal communication skills, tailored to diverse audiences. Capacity to quickly grasp complex issues, distill them to their essence, and offer strategic solutions. Credibility and confidence in interactions with senior leaders, including the ability to communicate candidly and deliver difficult feedback when necessary. Solid understanding of investment principles and experience working with investment professionals to achieve strong returns within established risk parameters. Deep knowledge of internal control design, implementation, and assessment.

Education & Experience

Bachelor's degree from an accredited institution, ideally with coursework in finance, accounting, or related fields. At least 10 years of progressive financial leadership experience; covering planning, reporting, systems, treasury, and taxation (required). Experience in financial management within the property and casualty insurance sector (preferred). Advanced degrees (i.e. MBA, Master's in Finance) and/or professional certifications (i.e. CPA, CMA, CFA) are advantageous.

Working Conditions

Hybrid work schedule: three days per week onsite in Chicago Occasional travel may be necessary based on business needs.

Compensation & Benefits

Offering comprehensive compensation package, including competitive salary, medical, dental, and vision insurance, 401(k), flexible spending accounts, and both short- and long-term disability coverage.

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