VP, Transformation & Strategy

The Vice President, Transformation & Strategy serves as a high-impact, senior enterprise leader responsible for shaping, prioritizing, and driving Ryan's transformation agenda to deliver measurable, sustained value creation. This role owns the integration of strategy, analytics, and execution discipline across the firm, ensuring that enterprise initiatives are rigorously prioritized, clearly quantified, and relentlessly tracked to outcomes. Reporting to the CTSO and partnering closely with executive leadership, the VP translates strategic ambition into executed results by ensuring completion of selected enterprise initiatives and accelerating change at scale. This role elevates Ryan's transformation capability to best-in-class standards by embedding financial and operational rigor, KPI discipline, and accountability into every major initiative, while enabling scalability, efficiency, controls, and superior client service. In particular, this role serves as a hands-on transformation leader to drive a complex, enterprise-wide transformation and IPO readiness program. This is a senior leadership role that must operate at both strategic and tactical levels-leading workstream project managers, managing complex dependencies, removing roadblocks, holding implementation partners accountable, and driving alignment and decisions across senior leadership. Duties and responsibilities Enterprise Program Leadership & Execution • Lead the integrated enterprise transformation and IPO readiness program across ERP, HCM, billing, CRM, data, integrations, and related business initiatives. • Lead and coordinate workstream project managers across functional and technical teams, ensuring alignment with the integrated program plan, milestones, dependencies, and delivery commitments. • Develop and maintain an integrated master program plan, including critical path, milestones, cross-workstream dependencies, resource requirements, and key decision points. • Proactively identify and remove roadblocks impacting program execution, working across teams and leadership to resolve issues, manage competing priorities, and maintain delivery momentum. Program Governance, Risk & Issue Management • Manage program governance, including leadership meetings, program reviews, stage gates, decision-making processes, and executive reporting. • Own the program's CRAID (Constraints, Risks, Actions, Issues, and Decisions) management process, ensuring clear ownership, mitigation plans, and timely resolution. • Drive issue resolution and escalation, ensuring critical risks, issues, and decisions are addressed at the appropriate leadership level with clear recommendations and actionable solutions. • Translate IPO and public company readiness requirements into defined deliverables, accountable owners, timelines, and dependencies, connecting technology delivery to SOX, financial close, revenue recognition, and audit readiness. • Provide concise, transparent executive updates on program health, progress, critical path, risks, and decisions requiring leadership attention. Stakeholder Leadership & Program Management Excellence • Facilitate executive and cross-functional working sessions to drive alignment, resolve competing priorities, and accelerate critical decisions. • Partners with internal client groups and executive leaders to identify, prioritize, and structure high-impact transformation initiatives aligned to Ryan's strategic objectives. • Serves as a trusted advisor to senior leadership by translating complex data, analytics, and scenarios into clear, actionable insights and recommendations. • Owns enterprise transformation value discipline, including value-at-stake identification, financial impact modeling, KPI definition, and benefits tracking. • Monitors transformation performance through dashboards, analytics, and structured reviews, identifying risks, gaps, and opportunities for course correction. • Influence senior stakeholders across the firm without relying on direct reporting authority. • Own and expand adoption of the organization's internal program management framework, methodologies, and tools across the business. • Lead a cross-functional transformation team, with direct reports added over time, while providing direction for existing Transformation & Strategy team members Education and Experience: • 15+ years of progressive experience in program management, enterprise transformation, or large-scale technology implementations, including leadership of complex, multi-year, cross-functional programs. • Hands-on experience with IPO or public company readiness initiatives, including an understanding of financial reporting, internal controls, SOX compliance, and operational readiness requirements. • Demonstrated success leading large-scale, complex ERP implementations through go-live, preferably involving Finance and HCM, multiple integrated platforms, and significant business process transformation. • Extensive experience leading and coordinating multiple workstream project managers, driving accountability, managing cross-functional dependencies, removing delivery roadblocks, and escalating critical issues to executive leadership. • Bachelor's degree required, preferably in business, finance, economics, engineering, analytics, or a related discipline. • Advanced degree (MBA or equivalent) strongly preferred. • Background in professional services, financial services, or another services business preferred Computer Skills: • Advanced proficiency in Microsoft Excel for financial modeling, scenario analysis, and performance measurement. • Expert-level PowerPoint skills for executive-ready presentations and strategic storytelling. • Experience with emerging analytical tools and techniques, including automation, machine learning, and AI-enabled insights • Experience with data visualization and dashboarding tools (e.g., Power BI, Tableau). • Familiarity with enterprise analytics platforms, BI environments, and performance reporting systems. • Smartsheet experience for enterprise program management, including integrated project plans, dashboards, automated reporting, and portfolio-level visibility; Smartsheet Control Center experience is a plus. Required Skills: • Exceptional analytical, quantitative, and problem-solving capability, with the ability to distill complexity into clear insights. • Advanced proficiency in enterprise program and project management methodologies, tools, and disciplines, including integrated master schedules, critical path analysis, CRAID management, stage gates, resource planning, and executive dashboards. • Demonstrated ability to identify and resolve complex program challenges, balance competing priorities, and drive decisions across multiple stakeholders. • Exceptional executive communication, facilitation, and stakeholder management skills, with the ability to influence senior leaders and drive accountability across organizational boundaries. • Excellent verbal and written communication skills, with the ability to translate data into compelling narratives for senior leaders. • Ability to collaborate effectively across functional groups and influence stakeholders without direct authority. • High degree of curiosity, initiative, and drive, with a commitment to continuous improvement and operational rigor. • Strong financial modeling skills and experience developing robust business cases. Preferred Skills: • Experience with Workday, a modern billing platform, or a large Salesforce redesign • Experience operating within or alongside a Transformation Office, Strategy function, or Value Realization Office. • Background in professional services or advisory environments with high expectations for rigor and client service. Certificates and Licenses: Valid driver's license required. Work Environment: • Standard indoor working environment. • Occasional long periods of sitting or standing while working. • Position requires regular interaction with employees and clients both in person and via e-mail and telephone. • Target in-office location (Plano): at least 3-4 days per week • Independent travel requirement: 10%.