Senior Director, Claims Technology Transformation & Delivery

Berkshire Hathaway Specialty Insurance•Boston, MA

3d•$155,000 - $175,000

About The Position

Berkshire Hathaway Specialty Insurance (BHSI) has an immediate opportunity for a Senior Director, Transformation & Delivery, to lead high‑impact initiatives within our Claims Technology organization. This role is ideal for a collaborative, execution‑focused leader who wants to shape the future of Claims through technology. You will help drive strategic programs including Claims 2.0 (core platform modernization), AI‑enabled Claims Automation, and greenfield Small Commercial Claims platform, directly influencing how Claims operates and scales. Partnering with senior business and technology leaders, you will guide cross‑functional teams, lead project managers and ensure delivery excellence in a regulated environment. At BHSI, Claims is our Product—and this role offers clear career growth, visibility, and the chance to define what’s next.

Requirements

Minimum of 10 years of experience in program and people management, including leading and managing complex systems projects; overall professional experience of at least 15 years.
Proven experience with enterprise technology systems, cloud platforms, and regulatory compliance.
Strong leadership, communication, and stakeholder management skills.
Attention to detail and the ability to multi-task while balancing diverse priorities.
Adept and eager to become engaged in a wide variety of business initiatives that require an understanding of diverse business, compliance, and technical topics.
Adept at rapidly responding to changes in priorities and deadlines.
Experienced in leading Agile software delivery models.

Responsibilities

Lead and deliver a portfolio of high impact, strategically aligned initiatives across Claims technology to drive business transformation and operational efficiency.
Ensure successful execution of core platform upgrade (Claims 2.0) program by aligning cross-functional collaboration with Underwriting, EDW, Security, and Infrastructure teams, ensuring timely delivery and business continuity.
Lead planning, execution, and delivery of AI‑enabled Claims Automation and a greenfield Small Commercial Claims platform as part of the Claims Technology portfolio.
Establish and maintain high standards for delivery excellence, risk mitigation, and stakeholder engagement to meet defined business goals.
Enhance transparency and compliance by evolving governance frameworks and documentation practices.
Lead and mentor a high-performing team of project managers, fostering a culture of accountability, innovation and continuous improvement to support evolving business needs.
Resolve cross-functional challenges by driving clarity in scope, stakeholder alignment, and facilitating timely issue resolution to maintain project momentum.
Provide executive-level visibility into program health through concise, data-driven reporting on status, risks, and interdependencies to support strategic decision-making.
Embed a continuous improvement mindset through structured post-implementation reviews and feedback loops to drive operational excellence and future readiness.