Director, Strategic Initiatives

Director of Strategic Initiatives

The Office of the CIO seeks a Director of Strategic Initiatives to support the Chief Innovation Officer and the VP of Innovation & Technology.

• Strategic Initiative Management: Track and drive accountability across the technology organization’s strategic initiatives. Maintain the initiative tracker, follow up on milestones, flag risks, and ensure work streams stay on timeline.
• Rhythm of Business: Own the operating cadence for the CIO’s office – monthly business reviews, quarterly planning sessions, annual budget cycles, and leadership team meetings. Build agendas, prepare pre‑reads, capture action items, and drive follow‑through.
• Executive Communications: Prepare executive‑level presentations, briefings, and decision packages for the CIO and VP of I&T. Translate complex operational details into clear, concise narratives for the CEO, board, and senior leadership team.
• Cross‑Departmental Coordination: Serve as the connective tissue between the technology organization and other business functions – Product, Sales, Finance, Operations, Compliance, and HR. Ensure the CIO’s priorities are understood across the company and manage cross‑departmental dependencies proactively.
• Transformation Orchestration: During the current organizational transformation, serve as the program manager for the restructure – tracking recruiting pipelines, partner onboarding milestones, communication plan execution, workforce transition sequencing, and operational readiness.
• Leadership Support: Support both the CIO and VP I&T with meeting preparation, stakeholder management, and ad‑hoc analysis. Represent the CIO’s office in meetings when leaders are unavailable and provide a trusted sounding board for strategic decisions.
• Budget and Resource Coordination: Support the annual budgeting process, track spend against budget, and provide variance analysis. Coordinate resource allocation discussions across the technology organization’s pillars. Assist in preparing technology updates for the board and investors, ensuring clear and compelling technology narratives, metrics, and strategic positioning.
• Special Projects: Own high‑priority special projects that don’t fit neatly into any single pillar – market analysis, organizational assessments, process improvements, competitive intelligence, or partnership evaluations. Deliver on these projects quickly and accurately.
• Information Flow: Ensure critical information flows up, down, and across the organization efficiently. Prevent surprises for leaders and eliminate confusion about priorities by managing the information architecture of the leadership team.

• Education: Bachelor’s degree in Business, Information Systems, Finance, or related field. MBA or Master’s degree preferred.
• Experience: Minimum 5+ years in chief of staff, strategy, management consulting, program management, or senior operations roles within technology organizations.
• Experience operating at the intersection of strategy and execution – able to think at a 30,000‑foot level and execute at the ground level in the same day.
• Exceptional written and verbal communication skills – capable of writing board‑level memos, presenting to C‑suite audiences, and engaging in direct conversations with directors.
• Strong analytical skills – comfortable with financial analysis, operational metrics, and data‑driven decision‑making.
• Experience managing complex, multi‑workstream initiatives with many stakeholders and moving parts.
• High emotional intelligence and political awareness – navigate organizational dynamics and ambiguity without creating confusion.
• Extreme ownership mentality – take initiative, identify needs, and drive execution without waiting for direction.
• Experience in technology organizations – understand how technology delivery works and translate technical concepts for business audiences.
• Discretion and confidentiality – access to sensitive information such as workforce planning, performance assessments, and strategic decisions. Absolute trustworthiness required.
• Experience in insurance, financial services, or other regulated industries is a plus.
• Military, management consulting, or…