Senior Director, Technology

Senior Director, Technology – Berkshire Hathaway Specialty Insurance

Apply now. Your pay will be based on experience; base salary is $155,000 – $175,000 per year .

Who are we?

A strategic and trusted insurance partner, BHSI provides a broad range of commercial property, casualty, and specialty insurance coverages and outstanding service to customers and brokers worldwide. Part of Berkshire Hathaway’s insurance operations, we bring our solutions to market with a stellar brand name, top‑rated balance sheet, and the expertise of a global team. We value respect, integrity, excellence, collaboration, and passion, and we strive to foster an inclusive environment that enables all team members to bring their best selves to work.

Job Opportunity

We have 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 high‑impact role will drive the successful delivery of multiple strategic technology programs, including Claims 2.0 (Core platform upgrade), Claims automation, and Small Commercial Claims initiatives. You will guide cross‑functional teams, mentor project managers, and ensure delivery excellence in a dynamic, regulated environment.

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 the core platform upgrade (Claims 2.0) program by coordinating 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 engage 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 customers, teammates, and our stakeholders.
• A purposely non‑bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework.
• Benefits that support life and well‑being, including:
• Comprehensive Health, Dental, and Vision benefits
• Disability Insurance (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 is determined by relevant skills, location, and experience. Note: Compensation will be commensurate with experience. This job description is not intended to be all‑inclusive. The team member may perform other related duties as negotiated to meet the ongoing needs of the organization.

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