Strategic Planning Expert (Chicago, IL)

At Allstate, great things happen when our people work together to protect families and their belongings from life’s uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers’ evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.  Job Description The Cybersecurity Strategic Planning Expert helps Allstate Cybersecurity & Controls (ACC) leaders turn complex cybersecurity risks, strategies, performance information, and technical initiatives into clear decisions, aligned action, and measurable outcomes. As part of the ACC Strategy team, this role develops compelling narratives and executive-ready communications for the Chief Information Security Officer (CISO), ACC leadership, senior executives, the Board, and the Audit Committee. Operating as a trusted advisor in an evolving and often ambiguous environment, the role brings structure to complex questions, synthesizes technical and business perspectives, and frames priorities, trade-offs, risks, and recommendations in concise, non-technical language. Success is reflected in stronger executive decision-making, consistent strategic narratives, greater visibility into cybersecurity posture and outcomes, clear accountability, and coordinated progress on the highest-priority risks. Key Responsibilities   • Develop clear, compelling cybersecurity narratives for the CISO, senior executives, Board, and Audit Committee.  • Translate complex cybersecurity risks, strategies, metrics, and technical initiatives into concise, non-technical, decision-ready communications.  • Create executive-level presentations and communications, including briefings, talking points, strategic reports, leadership updates, and Board materials.  • Support the development and governance of the Allstate Cybersecurity & Controls (ACC) strategy, ensuring alignment with enterprise priorities, business strategy, and the evolving cybersecurity risk environment.  • Monitor cybersecurity threats, regulatory developments, technology trends, and business changes to identify strategic implications and emerging priorities.  • Coordinate cross-functional strategic governance, including key commitments, portfolio outcomes, dependencies, risks, metrics, and leadership decisions.  • Measure and communicate strategic progress and cybersecurity outcomes through meaningful metrics, trends, gaps, and indicators of risk reduction.  • Analyze complex and ambiguous business and cybersecurity challenges, combining quantitative and qualitative information to develop practical recommendations.  • Frame strategic options, trade-offs, and recommendations and facilitate leadership discussions around prioritization, sequencing, and risk-informed decision-making.  • Build alignment across cybersecurity and enterprise partners, including Technology, Enterprise Risk, Legal, Compliance, Internal Audit, and Communications, while strengthening governance practices and team standards.    Required Education and Experience     • 4+ years of experience in strategy, executive communications, strategic planning, management consulting, business analysis, portfolio governance, risk, technology, financial services, or related roles.  • Demonstrated experience developing executive presentations, strategic narratives, briefing materials, or Board-facing content and synthesizing complex technical and business information into clear insights and recommendations.  • Experience supporting strategy development, governance, metrics, portfolio reporting, facilitation, cross-functional decision-making, or senior executive communications.  • Experience in cybersecu