VP, Sr Director, Technology - GDS Strategy & Planning

Liberty Mutual Insurance•Boston, MA

2d•$204,000 - $366,000

About The Position

The VP, Sr. Director of GDS Strategy and Planning is responsible for driving strategy, operating effectiveness, and organizational transformation across Global Digital Services. This role serves as a senior advisor to GDS leadership while owning strategic planning, portfolio and product governance, and delivery enablement across the organization. The position balances long-range strategic foresight, execution discipline, and enterprise alignment to enable technology modernization and business outcomes at scale.

Requirements

15+ years of experience in technology leadership, strategy, or consulting, with 5+ years in leadership roles.
Demonstrated experience leading large-scale transformation and operating model design.
Expertise in product, delivery, or portfolio management at enterprise scale.
Strong business acumen with the ability to connect technology strategy to measurable business outcomes.
Exceptional communication and influencing skills with senior and executive stakeholders.
Bachelor's degree in technical or business discipline or related experience.

Nice To Haves

Advanced degree (MBA, MS).
Experience in insurance or financial services.
Familiarity with product-centric and agile operating models.
Experience with enterprise communications, data, and analytics platforms.
Experience embedding technology resiliency, continuity, and risk management into strategic and operational planning.

Responsibilities

Support GDS leadership 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.
Serve as Chief of Staff to GDS leadership, managing operating cadence, communications, and decision frameworks.
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 GDS 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.
Shape and evolve planning and execution operating models that improve clarity, accountability, and speed across the technology organization.
Define and evolve operating models to improve speed, accountability, and cross-functional collaboration.
Enable strong partnerships across technology, finance, risk, and business stakeholders.
Leverage data, metrics, and scenario analysis to inform strategic choices and portfolio decisions.
Translate strategy into measurable outcomes and track progress against priorities.
Clearly communicate strategy, progress, and outcomes to executive stakeholders in a concise, business-oriented manner.