Director, Strategic Initiatives

Orion180•Melbourne, FL

2h•Onsite

About The Position

Orion180 is seeking a Director of Strategic Initiatives to serve the Office of the CIO, supporting both the Chief Information Officer and the VP of Innovation & Technology. This role is the operational and strategic nerve center for the technology organization - driving accountability across strategic initiatives, managing the rhythm of business, coordinating cross-departmental alignment, and ensuring leadership has the information and preparation they need to make decisions and execute at speed. The technology organization is in a period of significant growth and transformation. The Director of Strategic Initiatives will play a central role in orchestrating this transformation - tracking multiple concurrent workstreams, managing communication across stakeholders, preparing executive-level deliverables, and ensuring nothing falls through the cracks. As the transformation matures, the role evolves into the ongoing operational backbone of the CIO’s office. This is a hands-on role for someone who thrives in ambiguity, moves fast, and takes ownership. You won’t wait to be told what to do - you’ll see gaps and fill them. You’ll be equally comfortable preparing a board-level presentation and chasing down an overdue deliverable from a director. We value leaders who lead from the front and roll up their sleeves.

Requirements

Bachelor’s degree in Business, Information Systems, Finance, or related field.
Minimum 5+ years in Chief of Staff, strategy, management consulting, program management, or senior operations roles within technology organizations.
Demonstrated experience operating at the intersection of strategy and execution - you can think at the 30,000-foot level and execute at the ground level in the same day.
Exceptional communication skills - written and verbal. You can write a board-level memo, present to a C-suite audience, and have a direct conversation with a director about a missed deadline with equal confidence.
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 - you understand organizational dynamics, know when to push and when to listen, and can navigate ambiguity without creating confusion.
Extreme ownership mentality - you don’t wait for direction, you identify what needs to happen and make it happen. You hold yourself to a higher standard than anyone else holds you to.
Experience in technology organizations - you don’t need to be an engineer, but you need to understand how technology organizations operate, how delivery works, and how to translate technical concepts for business audiences.
Discretion and confidentiality - this role has access to sensitive organizational information including workforce planning, performance assessments, and strategic decisions. Absolute trustworthiness is non-negotiable.

Nice To Haves

MBA or Master’s degree preferred.
Experience in insurance, financial services, or other regulated industries is a plus.
Military, management consulting, or startup background is a plus - environments that value speed, adaptability, and getting things done with limited resources.

Responsibilities

Track and drive accountability across the technology organization’s strategic initiatives. Maintain the initiative tracker, follow up on milestones, flag risks, and ensure workstreams stay on timeline. You are the person who makes sure things don’t stall.
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.
Prepare executive-level presentations, briefings, and decision packages for the CIO and VP I&T. Translate complex operational details into clear, concise narratives for the CEO, board, and senior leadership team. You’ll be the person who turns a 50-page plan into a 5-slide executive summary.
Serve as the connective tissue between the technology organization and other business functions - Product, Sales, Finance, Operations, Compliance, and HR. Make sure the CIO’s priorities are understood across the company and that cross-departmental dependencies are managed proactively.
During the current organizational transformation, serve as the program manager for the restructure itself - tracking recruiting pipelines, partner onboarding milestones, communication plan execution, workforce transition sequencing, and operational readiness. Make sure all workstreams are coordinated and leadership has visibility into overall progress.
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 neither leader can attend. Provide a trusted sounding board for strategic decisions.
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. Ensure technology narrative, metrics, and strategic positioning are clear and compelling.
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. These are the projects that the CIO or VP I&T need done right and done fast.
Ensure critical information flows up, down, and across the organization efficiently. The CIO and VP I&T should never be surprised by something they should have known. Directors should never be confused about priorities. You manage the information architecture of the leadership team.