VP, Transformation & Strategy

Ryan • Plano, TX

4d • Hybrid

About The Position

The Vice President, Transformation & Strategy is a senior enterprise leader responsible for shaping, prioritizing, and driving Ryan’s transformation agenda to deliver sustained, measurable value. Reporting to the CTSO and partnering with executive leadership, the VP integrates strategy, analytics, and execution discipline across the firm, translating strategic priorities into completed enterprise initiatives and scalable change. The role embeds financial and operational rigor, KPI discipline, and accountability into major initiatives to support scalability, efficiency, controls, and client service.

The VP leads a complex, enterprise-wide transformation and IPO readiness program spanning ERP, HCM, billing, CRM, data, integrations, and related business initiatives. The role operates at strategic and tactical levels, coordinating workstream project managers, maintaining the integrated program plan, managing dependencies, removing roadblocks, holding implementation partners accountable, and driving alignment and decisions among senior leaders.

This position owns program governance, risk and issue management, executive reporting, and the translation of IPO and public-company readiness requirements into defined deliverables, owners, timelines, and dependencies. It connects technology delivery with SOX, financial close, revenue recognition, and audit readiness. The role also leads transformation value discipline through financial impact modeling, KPI definition, benefits tracking, dashboards, analytics, and structured reviews. It leads a cross-functional transformation team, provides direction to existing Transformation & Strategy team members, and may gain direct reports over time.

The role requires a bachelor’s degree and at least 15 years of progressive experience in program management, enterprise transformation, or large-scale technology implementations. An advanced degree is strongly preferred. The target in-office location is Plano, with at least 3–4 days per week in the office and an independent travel requirement of 10%.

Requirements

• 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 knowledge 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 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.
• Valid driver’s license required.
• 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 such as Power BI or 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.
• 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, including the ability to influence senior leaders and drive accountability across organizational boundaries.
• Excellent verbal and written communication skills, including 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.

Nice To Haves

• Advanced degree (MBA or equivalent).
• Background in professional services, financial services, or another services business.
• Smartsheet Control Center experience.
• 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.

Responsibilities

• Lead the integrated enterprise transformation and IPO readiness program across ERP, HCM, billing, CRM, data, integrations, and related business initiatives.
• 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 the critical path, milestones, cross-workstream dependencies, resource requirements, and key decision points.
• Identify and remove roadblocks to program execution, resolving issues and competing priorities across teams and leadership.
• Manage program governance, including leadership meetings, program reviews, stage gates, decision-making processes, and executive reporting.
• Own the CRAID (Constraints, Risks, Actions, Issues, and Decisions) management process, with clear ownership, mitigation plans, and timely resolution.
• Drive issue resolution and escalation, providing clear recommendations and actionable solutions for leadership decisions.
• Translate IPO and public-company readiness requirements into deliverables, accountable owners, timelines, and dependencies, connecting technology delivery to SOX, financial close, revenue recognition, and audit readiness.
• Provide transparent executive updates on program health, progress, critical path, risks, and decisions requiring leadership attention.
• Facilitate executive and cross-functional working sessions to drive alignment, resolve competing priorities, and accelerate decisions.
• Partner with internal client groups and executive leaders to identify, prioritize, and structure transformation initiatives aligned with Ryan’s strategic objectives.
• Advise senior leadership by translating complex data, analytics, and scenarios into actionable insights and recommendations.
• Own enterprise transformation value discipline, including value-at-stake identification, financial impact modeling, KPI definition, and benefits tracking.
• Monitor transformation performance using 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.
• Expand adoption of the organization’s internal program management framework, methodologies, and tools across the business.
• Lead a cross-functional transformation team, provide direction to existing Transformation & Strategy team members, and build direct reports over time.

Benefits

• Health, dental, and vision coverage effective on the first day for the employee and eligible dependents.
• 14 weeks of 100% paid leave for new parents, including adoption.
• Fertility assistance program.
• Generous paid time off.
• Eligibility for a four-week, company-paid sabbatical after five years of service.
• 401(k) employer match after one year of service.
• Tuition reimbursement after one year of service.
• Monthly gym membership or reimbursement for eligible home fitness equipment.
• Hybrid and remote work options, depending on the role.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior