Director, Engineering - Policy Migration - USRM Tech

Liberty Mutual Insurance•Boston, MA

About The Position

Liberty Mutual US Retail Markets (USRM) Technology is undertaking a multi-year transformation to modernize our policy administration ecosystem by converging legacy platforms into a unified, cloud-enabled Guidewire PolicyCenter solution. We are seeking a Director of Engineering – Policy Migration to lead one of the most critical components of this transformation: the end-to-end migration of legacy policies, data, and capabilities into our modern platform. This leader will define and execute the engineering and data migration strategy, build and lead a high-performing organization, and partner across Product, Underwriting, Data, and Platform teams to ensure seamless, high-quality migration outcomes that enable business agility and customer value. This role combines deep technical leadership, large-scale program execution, and organizational leadership, and is pivotal to delivering a simplified, future-ready insurance platform.

Requirements

Bachelor’s or Master’s degree in Computer Science, Engineering, or related discipline.
10+ years of technology experience with 5+ years in senior leadership roles.
Experience leading large-scale policy administration transformations in P&C insurance.
Deep expertise in Guidewire PolicyCenter (Guidewire Cloud preferred).
Strong experience with large-scale data migration, ETL/ELT, reconciliation, and production cutovers.
Proven ability to lead large, globally distributed engineering teams (75–150+ engineers).
Strong knowledge of cloud-native architectures, microservices, APIs, and DevOps practices.
Demonstrated ability to lead complex, cross-functional programs and influence senior stakeholders.
Strong business acumen with the ability to align technology outcomes to business strategy.

Nice To Haves

Guidewire Cloud preferred

Responsibilities

Build, lead, and develop a high-performing engineering organization, including engineering managers and senior technical leaders.
Foster a culture of technical excellence, innovation, accountability, and continuous learning.
Oversee talent strategy including hiring, coaching, performance management, and succession planning.
Establish and scale global engineering teams, including vendor and offshore strategies aligned to capacity and cost objectives.
Define and lead the end-to-end policy and data migration strategy, including mapping, transformation, trial conversions, reconciliation, and production cutover.
Establish data quality, validation, auditability, and reconciliation frameworks to support go/no-go decisions and regulatory compliance.
Drive execution of conversion-at-renewal and other migration patterns, ensuring alignment to program milestones and business priorities.
Lead cross-functional coordination across Guidewire, system integrators, platform teams, and downstream consumers to manage dependencies, risks, and delivery.
Shape and drive engineering strategy aligned with enterprise architecture, modern engineering practices, and cloud-native platforms.
Lead design and implementation of scalable, resilient solutions within the Guidewire PolicyCenter ecosystem.
Ensure adoption of best practices across software development, DevOps, security, and quality engineering.
Balance speed-to-market with long-term scalability, reliability, and operational excellence.
Partner with Product, Underwriting, Data, Experience, and Architecture teams to deliver business value and seamless customer experiences.
Collaborate with senior and executive leadership to align engineering priorities with enterprise strategy and modernization goals.
Own delivery outcomes, including timelines, quality, system health, and business impact.
Represent engineering in strategic planning, budgeting, and resource allocation discussions.
Serve as a thought leader in engineering and modernization, influencing architecture, platform investments, and emerging technologies (e.g., GenAI, cloud data platforms).
Advance engineering practices and contribute to Liberty Mutual’s broader technology community.
Lead and develop a high-performing engineering organization, including managers, senior engineers, and global/vendor teams.
Own the end-to-end policy and data migration strategy, including mapping, transformation, trial conversions, reconciliation, cutover, and stabilization.
Be accountable for delivery of migration milestones across a multi-year modernization program.
Establish data quality, validation, auditability, and reconciliation frameworks to support regulatory and business requirements.
Drive cross-functional execution across Guidewire, system integrators, platform teams, and downstream systems.
Shape engineering strategy aligned with enterprise architecture, cloud platforms, and long-term modernization goals.
Ensure adoption of best practices across software engineering, DevOps, security, and reliability.
Partner with Product, Underwriting, Data, and Experience teams to deliver measurable business outcomes.
Represent engineering in executive-level planning, funding, and prioritization discussions.
Build a strong engineering culture focused on accountability, innovation, and continuous improvement.
Serve as a thought leader influencing engineering practices and enterprise technology direction.