Director of Transformation

Job Description

Insight Global is seeking a Director of Strategy & Transformation for a client. This person will own multiple high-priority transformation workstreams across the organization. This person will operate at the intersection of strategy, execution, and executive leadership, helping translate major business priorities into structured programs with measurable outcomes. This is a highly visible role requiring someone who can quickly understand complex business problems, build the right operating cadence and metrics, and confidently present progress, decisions, risks, and recommendations to senior leadership and the Board.

• Own two major transformation workstreams within a broader portfolio of approximately 10 enterprise initiatives.
• Develop the structure, roadmap, milestones, and success metrics needed to manage long-term transformation programs.
• Define and track KPIs and business metrics that demonstrate whether transformation initiatives are delivering the intended outcomes.
• Build business cases for new initiatives and help prioritize and manage the broader transformation portfolio.
• Lead the weekly operating cadence for assigned workstreams, including agendas, meeting facilitation, decision tracking, risks, action items, and follow-up.
• Meet with key stakeholders throughout the week to understand progress, surface issues, and prepare recommendations for executive reviews.
• Prepare materials and insights for Board-level meetings, often with short turnaround times.
• Translate conversations, data, and business developments into concise, executive-ready presentations and written updates.
• Produce a weekly written recap summarizing progress, decisions, risks, actions, and next steps.
• Partner cross-functionally with business leaders to keep large, high-stakes transformation initiatives on track.
• Bring structure to ambiguous problems and proactively determine what leadership needs to know or decide.

Skills and Requirements

• Significant transformation experience, ideally within management consulting, strategy consulting, enterprise transformation, or a comparable internal transformation function.
• Experience leading long-term, high-stakes transformation programs involving multiple senior stakeholders and complex business initiatives.
• Strong executive presence, including experience preparing for and presenting to executives, senior leadership teams, or Boards.
• Ability to take an ambiguous business problem and create structure around it, including business cases, KPIs, milestones, governance, and measurable outcomes.
• Strong program and portfolio management capabilities, with experience owning multiple strategic workstreams simultaneously.
• Excellent executive communication and presentation skills, including the ability to produce polished content quickly.
• Comfortable working in a fast-paced environment with high expectations and visibility.
• Able to work onsite four days per week in Orlando.
• Background with a top consulting organization such as McKinsey, Accenture, or a similar firm.
• Experience moving from external consulting into an internal corporate strategy or transformation role.
• Private equity portfolio company experience or experience supporting transformation/value-creation initiatives in a PE environment.
• Hospitality, travel, vacation ownership, or another consumer-facing industry background.
• Experience managing enterprise transformation portfolios with several parallel workstreams.
• Experience developing materials for Boards or executive steering committees.

We are a company committed to creating diverse and inclusive environments where people can bring their full, authentic selves to work every day. We are an equal employment opportunity/affirmative action employer that believes everyone matters. Qualified candidates will receive consideration for employment without regard to race, color, ethnicity, religion, sex (including pregnancy), sexual orientation, gender identity and expression, marital status, national origin, ancestry, genetic factors, age, disability, protected veteran status, military or uniformed service member status, or any other status or characteristic protected by applicable laws, regulations, and ordinances. If you need assistance and/or a reasonable accommodation due to a disability during the application or the recruiting process, please send a request to [email protected].