Strategic Planning Expert (Chicago, IL)

Allstate • Chicago, IL

6d • $100,000 - $170,500

About The Position

The Cybersecurity Strategic Planning Expert is part of Allstate Cybersecurity & Controls (ACC) Strategy and helps ACC leaders turn complex cybersecurity risks, strategies, performance information, and technical initiatives into clear decisions, aligned action, and measurable outcomes. The 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.

Working 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 includes stronger executive decision-making, consistent strategic narratives, increased visibility into cybersecurity posture and outcomes, clear accountability, and coordinated progress on high-priority risks.

The position is based in Chicago, Illinois, and requires the ability and willingness to travel to the Chicago office as needed. Compensation is $100,000–$170,500 annually, based on experience and qualifications. Candidates offered the position must submit to a background investigation. Allstate generally does not sponsor individuals for employment-based visas for this position.

Requirements

• At least 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.
• Must be willing and able to travel to the Chicago, Illinois office as needed.

Nice To Haves

• Experience in cybersecurity, technology, risk, consulting, financial services, insurance, or another complex regulated environment.

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 development and governance of the 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 using 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 about 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.

Benefits

• Comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse.
• Eligible employees working from home receive a monthly connectivity reimbursement to help offset internet costs.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed