Sr Director, Strategy and Planning - Investments, Data, Experience

Liberty Mutual Insurance•Boston, MA

About The Position

Liberty Mutual is seeking a Senior Director of Strategy, Planning, and Resiliency for our Investments, Data, and Experience technology division. Reporting to the Chief Technology Officer, the senior director will facilitate strategic planning and lead resiliency efforts for the LMI Technology, Enterprise Data and Analytics Technology (EDATA), and Intelligent Work Platforms. The role balances strategic foresight, operational rigor, and risk-informed decision-making, with a strong emphasis on building and running resilient technology ecosystems that can withstand disruption, scale with growth, and enable innovation, while enabling modernization and innovation across the enterprise.

Requirements

Bachelor's or Master's Degree in technical or business discipline or related experience; Master's Degree preferred
Generally a minimum of 15 years related experience with 5 years in leadership role desirable
Deep domain expertise with harnessing technology to modernize and shape investment and asset management capabilities
Expertise in enterprise scale, modern data, data analytics, and data science platforms and technology strategy
Demonstrated experience managing large complex programs and flagship initiatives, leveraging the execution blueprint ensuring best practices
Demonstrated success governing complex portfolios and aligning investments to business outcomes
Strong understanding of modern enterprise technology environments, including platforms, infrastructure, cloud, data, and integration ecosystems
Experience embedding technology resiliency, continuity, and risk management into strategic and operational planning
Enterprise-first mindset with strong strategic judgment
Ability to influence senior leaders and diverse stakeholder groups
Clear, confident communicator of complex topics
Bias toward action, outcomes, and accountability
Resilient leader who enables stability while driving change

Responsibilities

Support the CTO by orchestrating strategic planning, executive communications, and cross portfolio alignment, ensuring priorities are clearly articulated, decisions are well‑informed, and outcomes are tracked and delivered.
Act as a trusted advisor to senior business and technology leaders, providing strategic insight on trade-offs, sequencing, and investment decisions.
Facilitate executive-level discussions to align priorities, progress, outcomes, and risk posture.
Lead annual and long-range technology planning processes, including prioritization, demand management, funding, and strategic workforce planning.
Establish and mature governance practices that promote transparency, disciplined execution, and measurable value realization across the technology portfolio.
Ensure investment decisions balance modernization, operational stability, and long-term sustainability.
Champion enterprise tooling and process alignment, enabling teams with clear standards and expectations while reinforcing accountability for consistent execution and measurable impact.
Set strategic direction for technology resiliency, including availability, recoverability, reliability, and continuity of critical technology services.
Partner with infrastructure, architecture, security, and operations leaders to embed resiliency principles into platforms, applications, and services.
Ensure technology strategies proactively address business continuity, disaster recovery, systemic risk, and operational resilience.
Oversee incident and change management practices for the organization and ensure they are measured and continuously improved.
Integrate technology risk considerations into strategic planning and decision-making.
Strengthen department’s ability to operate safely, securely, and reliably in support of regulatory expectations and customer trust.
Shape and evolve planning and execution operating models that improve clarity, accountability, and speed across the technology organization.
Enable strong cross-functional collaboration across technology, finance, risk, and business partners.
Establish and reinforce expectations for system hygiene across the application portfolio, holding product and application teams accountable for lifecycle management, technical debt reduction, risk remediation, and adherence to enterprise standards that support stability, security, and resiliency.
Leverage data, metrics, and scenario analysis to inform strategic choices and portfolio decisions.
Clearly communicate strategy, progress, and outcomes to executive stakeholders in a concise, business-oriented manner.