Director of Strategic Finance & Business Partnering - CIO

Director Of Strategic Finance & Business Partnering – CIO

We're determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.

This role partners directly with Technology and Segment Finance leadership to drive financial transparency, modernize forecasting and reporting, and enable faster, earlier, and more actionable insights across run and invest spend.

This position leads a team and is accountable for advancing the Technology Finance operating model by leveraging AI, automation, driver-based financial modeling, and cross-finance partnership to reduce manual effort, improve forecast quality, and deliver proactive insight into cost drivers, allocation impacts, and business outcomes.

Executive-Level Business Partnership & Influence

• Serve as a strategic advisor to Technology and Finance leadership, providing clear financial insights, recommendations, and decision frameworks
• Translate complex financial results, technology drivers, and allocation impacts into actionable guidance for executive decision-making
• Deliver concise, executive-ready commentary that moves beyond variance reporting to explain risks, opportunities, tradeoffs, and required actions

Segment Finance Partnership, Allocation Transparency & Technology Spend Management

• Strengthen cost transparency by identifying and explaining key drivers of Technology and infrastructure spend, including direct and indirect cost impacts
• Partner with Segment Finance to evolve Technology allocation reporting, provide proactive transparency into direct and indirect allocation impacts - so segment impacts are understood earlier, explained consistently, and used to inform business.

End-to-End Financial Modeling & Insight Generation

• Lead development of Operating Plan, forecasts, monthly results, and driver-based financial models that connect technology activity to financial outcomes
• Shift reporting from retrospective variance explanation to forward-looking insight by identifying trends, risks, opportunities, and allocation impacts earlier in the cycle
• Improve forecast predictability through stronger governance, consistent assumptions, scenario modeling, and alignment to approved decisions
• Create scalable materials and commentary that reduce manual work while increasing the quality, consistency, and actionability of insights delivered to leadership

Finance Modernization / Transformation Leadership

• Lead the roadmap to modernize Technology Finance forecasting, reporting, allocation transparency, and analytics
• Leverage AI, automation, and reusable workflows to reduce manual effort, shorten cycle times, and improve consistency of leadership materials
• Redesign recurring reporting and Outlook processes so finance effort shifts from data assembly to insight generation, challenge, and decision support
• Build team adoption of modern tools, standardized prompts, automated diagnostics, and human-in-the-loop review to improve speed, quality, and control

Team Leadership & Capability Development

• Lead, coach, and develop a high-performing finance team
• Establish clear expectations for ownership, accountability, and quality of work
• Build team capability in financial modeling, analytics, and business partnership
• Foster a culture of continuous improvement and engagement

Core FP&A Foundations

• Lead financial management of Technology spend, including run vs. invest, capital vs. expense, lifecycle funding, and portfolio tradeoffs
• Own financial reporting, variance analysis, and executive commentary
• Ensure accuracy, compliancy, and integrity of financial information, including capitalization, allocations, and reserves
• Provide oversight of contracts, invoices, and asset-related financial activities

Qualifications

This role will have a Hybrid work arrangement, with the expectation of working in the office (Hartford, CT) 3 days a week (Tuesday through Thursday).

• Bachelor's degree in Finance, Accounting, or related field required; MBA or CPA preferred
• 10+ years of finance experience, including FP&A, expense…