Director, IT Strategy and Planning - Hybrid or Remote Opportunity

GuideOne Insurance • New York, NY • 2h ago

The Director of IT Strategy and Planning serves as a strategic and operational partner to the Chief Information and Technology Officer (CITO), playing a critical role in shaping and executing the organization's technology vision. This leader is responsible for driving alignment across the enterprise, ensuring that IT initiatives are clearly defined, well-communicated, and effectively implemented.

This role oversees the development and articulation of 6-, 12-, and 18-month IT strategies, facilitates planning processes, and fosters organizational clarity and focus within the IT function. By combining strategic foresight with operational coordination, the Director enables the CITO and IT leadership team to remain focused on enterprise priorities while ensuring cohesive execution across all teams.

Accountabilities:

Strategic Technology Planning

Lead the creation and evolution of a multi-horizon multi-member IT strategy that reflects business priorities and technology innovation.

Translate strategic themes into clear, actionable roadmaps across Infrastructure, Security, Applications, Data, and Operations.

Monitor external trends and internal capabilities to identify strategic opportunities and gaps.

Technology Governance & Execution Rhythm

Establish and manage the IT strategy calendar, including quarterly planning sessions, strategic reviews, roadmap check-ins, and milestone tracking.

Coordinate prioritization processes and cross-functional alignment across business and IT stakeholders.

Ensure timely visibility into key strategic decisions, actions, and risks to support organizational momentum.

Operational Leadership Support

Support the CITO and IT leadership team by organizing leadership forums, tracking commitments, and ensuring follow-through on strategic initiatives.

Drive the preparation of executive updates, board materials, and strategic communications from the Office of the CITO.

Serve as the central coordination point for progress tracking, decision-making frameworks, and reporting.

Portfolio Oversight & Strategic Roadmap Delivery

Lead integrated planning, reforecasting, and prioritization cycles to adapt roadmaps based on business or technology shifts.

Track and analyze initiative KPIs, ensuring delivery aligns with enterprise outcomes and IT value creation goals.

Cross-Functional Alignment

Act as a connector between IT, Finance, and business teams to align strategy, investment planning, and operational execution.

Partner with Finance to support IT budget planning, cost optimization, and long-range investment mapping.

Coordinate with the Enterprise Architecture, Security, and Infrastructure teams to ensure strategic and architectural alignment.

Vendor Collaboration

Engage with the Vendor Management team (TMG) to ensure third-party capabilities are aligned with strategic technology goals.

Coordinate vendor planning and intake without direct oversight of contracts or procurement.

Qualifications:

12+ years of experience in IT strategy, enterprise planning, business operations, or consulting within technology-driven environments.

5+ years working in close partnership with executive leadership; experience organizing and facilitating leadership forums and planning processes.

Proven success in developing and operationalizing multi-year IT strategies and integrated portfolios.

Deep understanding of cloud platforms, enterprise IT environments, and emerging technologies.

Strong communication, facilitation, and organizational skills-able to synthesize complexity and drive clarity across stakeholders.

Business acumen and financial fluency to connect IT investments with value delivery.

Benefits:

We are proud to offer a robust benefits suite that includes:

Competitive base salary plus incentive plans for eligible team members

401(K) retirement plan that includes a company match of up to 6% of your eligible salary

Free basic life and AD&D, long-term disability and short-term disability insurance

Medical, dental and vision plans to meet your unique healthcare needs

Wellness incentives

Generous time off program that includes personal, holiday and volunteer paid time off

Flexible work schedules and hybrid/remote options for eligible positions

Educational assistance

TMG

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