Carrie Woodrum

Lead enterprise-wide strategy and execution for Markel’s Strategic Data Program, aligning data capabilities with business priorities across underwriting, claims, finance, and operations. Drive program governance, cross-functional collaboration, and roadmap delivery to advance the organization’s future-state data architecture and governance maturity.

• Defined and operationalized the enterprise data strategy through a multi-year Strategic Data Program aligned to business and operational goals.
• Partnered with senior leaders and the Data & Analytics Transformation Team (DATT)—a C-suite governing body acting as the Chief Data Officer—to secure alignment, sponsorship, and strategic guidance.
• Led cross-functional strategy definition with stakeholders in underwriting, claims, operations, finance, and IT to surface business needs and define future-state data capabilities.
• Built the roadmap to target-state architecture and governance, including sequencing, funding alignment, and capability development.
• Identified and addressed cultural gaps in data governance execution, defining roles, ownership models, and data quality expectations.
• Oversaw execution across interdependent initiatives, managing risks, dependencies, and cross-team coordination.
• Delivered executive reporting, strategic plans, and maturity assessments to support governance and drive enterprise decision-making.

Led SingleStone’s centralized delivery function, overseeing a portfolio of 30+ concurrent client engagements spanning people, process, and technology. Built and scaled PMO-aligned delivery governance, established quality benchmarks, and drove client satisfaction through operational discipline, strategic planning, and team enablement.

• Directed a high-performing team of Delivery Leaders accountable for end-to-end client execution, ensuring outcomes were met or exceeded across timeline, scope, and client satisfaction.
• Implemented standardized delivery frameworks, project management expectations, and quality controls to drive consistency across engagements.
• Achieved and sustained client Net Promoter Scores (NPS) above 70% through rigorous delivery oversight, proactive risk management, and strong stakeholder alignment.
• Designed and operationalized a customer success interaction model to streamline escalations and capture actionable qualitative and quantitative feedback.
• Developed a performance-based renewal incentive strategy for Delivery Leads, resulting in 2 contract renewals within the first 30 days and 5 new opportunities entering the pipeline.
• Initiated the build-out of a Change Management service offering and team structure to expand the firm’s capabilities and better support client transformation journeys.
• Served as a strategic advisor to internal stakeholders and clients, ensuring delivery teams were equipped with tools, methodologies, and guidance to manage complex, multi-stakeholder initiatives.

Initiated efforts to expand SingleStone’s footprint in the public sector by laying the groundwork for federal engagement, developing foundational strategies, and aligning internal teams for long-term growth.

• Began leading SingleStone through the foundational steps required for Federal Facility Clearance (FCL), positioning the firm for future eligibility to pursue federal contracts.
• Initiated relationship-building efforts with key government agencies and public sector stakeholders, identifying decision-makers and developing early-stage engagement strategies.
• Collaborated cross-functionally with marketing, solution leads, recruiting, and project support to align offerings with public sector requirements and expectations.
• Developed initial public sector sales strategies, including early-stage account planning, prospect identification, and opportunity qualification.
• Conducted preliminary market and competitive analysis to identify areas of opportunity and inform long-term public sector positioning.
• Established a strategic foundation for entering the federal and broader public sector markets, aligning go-to-market planning with operational readiness.

Directed portfolio governance and program delivery oversight for Operational Risk Management, aligning regulatory compliance initiatives with enterprise-wide risk reduction strategies and PMO best practices.

• Developed and executed a portfolio management strategy that reduced regulatory/audit exposure and achieved over 50% reduction in staffing costs over two years.
• Led cross-functional programs to address complex regulatory findings, including MRIA remediation, Audit & Exam management, and strategic workforce planning.
• Served as a central PMO leader across risk-driven initiatives, providing strategic delivery oversight, risk mitigation planning, and execution governance.
• Partnered with internal risk stakeholders—Compliance, Ethics, Investigations, and Operational Risk—to drive alignment across business priorities and regulatory expectations.
• Provided strategic guidance to project teams and senior stakeholders, ensuring disciplined delivery, clear accountability, and measurable outcomes.
• Influenced and enabled delivery teams (both direct and matrixed) to operate within a structured governance model while addressing dynamic risk and regulatory needs.
• Selected as program lead for several enterprise-critical risk initiatives due to demonstrated ability to balance delivery rigor with strategic adaptability.

Established and led a mature Project Management Office (PMO) supporting Enterprise HR (EHR) initiatives across the U.S. and U.K., delivering consistent, high-quality execution for high-impact programs through disciplined governance, resource optimization, and strategic alignment.

• Led and developed a team of 12 Project Managers and Scrum Masters, providing hands-on coaching, career pathing, and performance management to build a high-performing delivery organization.
• Oversaw planning and delivery of complex, cross-functional initiatives supporting EHR’s digital transformation, aligning execution to strategic objectives and stakeholder expectations.
• Designed and implemented an enterprise-wide intake, prioritization, and resourcing framework, creating transparency across seven resource groups and enabling efficient, value-based resource allocation.
• Partnered with senior HR leaders to define strategic intent, delivery approaches, and execution support models that advanced business outcomes and operational excellence.
• Owned and managed multiple strategic implementation plans, including experience-based resource placement to ensure the right talent supported the most critical EHR initiatives.
• Provided scalable project and agile delivery capabilities to support evolving enterprise HR needs, integrating governance and flexibility across delivery models.
• Managed third-party delivery partners and external suppliers to ensure accountability, consistent quality, and alignment with internal delivery standards and expectations.

• Managed 12 associates delivering across multiple Enterprise Human Resources initiatives in the US, UK, Philippines, India and Canada. Drove successful execution of some of the most critical and complex multi year initiatives through close partnership with Senior Leaders.

• Delivering on Integration Programs tied to legal entity mergers, customer and associate experience, brand conversions, regulatory finding remediation and target domain architecture efforts for business integrations with a lens towards mitigating critical impacts and highlighting positive changes through various channels and methodologies.