Senior Director, Technology

Job Opportunity:

Berkshire Hathaway Specialty Insurance (BHSI) has an exciting and immediate opportunity for a collaborative and execution-focused Senior Director of Technology to lead major initiatives within our Claims Technology team. This is a high-impact role responsible for driving the successful delivery of multiple strategic technology programs including Claims 2.0 (Core platform upgrade), Claims automation and Small Commercial Claims initiatives to further strengthen our claims operations. This is an opportunity to shape the future of Claims operations at BHSI through transformative technology projects. The successful candidate will guide cross-functional teams, mentor project managers, and ensure delivery excellence in a dynamic, regulated environment. At BHSI, Claims is our Product!

Duties and 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.
• 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.

Qualifications, Skills, and Experience:

• 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.

BHSI Offers:

• A competitive package and exciting growth opportunities for career-oriented teammates.
• A dynamic, action oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and our other stakeholders.
• A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework. Benefits that support your life and well-being, which include: Comprehensive Health, Dental and Vision benefits Disability Insurance (both short-term and long-term) Life Insurance (for you and your family) Accidental Death & Dismemberment Insurance (for you and your family) Flexible Spending Accounts Health Reimbursement Account Employee Assistance Program Retirement Savings 401(k) Plan with Company Match Generous holiday and Paid Time Off Tuition Reimbursement Paid Parental Leave

The base salary range for this position in Boston is $155,000 to $175,000, along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates – both their capabilities and character – as demonstrated by our amazing culture.