VP, Transformation & Strategy

Ryan • Plano, TX

2d • 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 measurable, sustained value. The role integrates strategy, analytics, and execution discipline across the firm, ensuring enterprise initiatives are prioritized, quantified, and tracked to outcomes. Reporting to the CTSO and working closely with executive leadership, the VP translates strategic objectives into completed initiatives and accelerates enterprise change.

The role leads a complex, enterprise-wide transformation and IPO readiness program spanning ERP, HCM, billing, CRM, data, integrations, and related business initiatives. It embeds financial and operational rigor, KPI discipline, and accountability into major initiatives while supporting scalability, efficiency, controls, and client service. The VP operates at strategic and tactical levels, coordinating workstream project managers, managing dependencies, removing roadblocks, holding implementation partners accountable, and driving decisions across senior leadership.

The position leads program governance, risk and issue management, executive reporting, and IPO-readiness delivery planning. It also owns transformation value discipline, including financial impact modeling, KPI definition, benefits tracking, and performance monitoring. The VP leads a cross-functional transformation team, with direct reports added over time, and provides direction to existing Transformation & Strategy team members. The target in-office location is Plano, with at least three to four days per week in 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 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 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 capabilities, including 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.
• 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, 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.
• Valid driver’s license required.

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 to align with the integrated program plan, milestones, dependencies, and delivery commitments.
• Develop and maintain an integrated master program plan covering critical path, milestones, cross-workstream dependencies, resource requirements, and key decision points.
• Identify and remove execution roadblocks, resolving issues and competing priorities across teams and leadership to maintain delivery momentum.
• 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) process, ensuring clear ownership, mitigation plans, and timely resolution.
• Drive issue resolution and escalation, bringing critical risks, issues, and decisions to the appropriate leadership level with recommendations and actionable solutions.
• 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 concise executive updates on program health, progress, critical path, risks, and decisions requiring leadership attention.
• Facilitate executive and cross-functional working sessions to build alignment, resolve competing priorities, and accelerate decisions.
• Partner with internal client groups and executive leaders to identify, prioritize, and structure high-impact 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 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.
• 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 manage direct reports as they are added 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.
• Tuition reimbursement after one year of service.
• Monthly gym membership or eligible home fitness equipment reimbursement.
• Hybrid and remote work options, depending on the role.

What This Job Offers

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