Who are we?
A strategic and trusted insurance partner, Berkshire Hathaway Specialty Insurance (BHSI), provides a broad range of commercial property, casualty and specialty insurance coverages and outstanding service to customers and brokers around the world. Part of Berkshire Hathaway’s insurance operations, we bring our solutions to market with our stellar brand name, top-rated balance sheet, and the expertise of our global team of professionals, who exude excellent capabilities and strong character.
We are a values-based organization where respect, integrity, excellence, collaboration, and passion define who we are and how we do business. We value diversity of backgrounds, experience, and perspectives and strive to foster an inclusive environment that enables all our team members to bring their best selves to work. We are one team committed to building a culture where every teammate has the opportunity to contribute and be recognized. Want to be part of the team building the finest property, casualty, and specialty lines insurance company in the world?
Learn more about our unique culture and history .
Job Opportunity
Berkshire Hathaway Specialty Insurance (BHSI) has an exciting opportunity for an experienced technology portfolio leader to join our Boston-based Technology team as AVP, Strategy & Planning - Portfolio Management. This is a unique opportunity to join a global organization and drive meaningful change in how we work.
This critical role sits within our Technology Strategy & Planning team and will bring transparency and discipline into how initiatives are received, evaluated, prioritized, tracked, and measured for our global technology portfolio. This role will partner closely with executive and senior leaders (technology and business) across regions (North America, Europe, Asia Middle East, and Australasia) and global functions to ensure strategic priorities translate into executable plans and measurable outcomes.
A key focus of this role is building the foundational capabilities to enable enterprise portfolio excellence in both process and tooling. You will facilitate governance forums, define ownership and decision rights, establish clear prioritization criteria, and introduce consistent success metrics. You will facilitate planning for the annual budget cycle. You will collaborate closely with agile delivery leaders and other departments to select and implement a portfolio management tool and governance process that integrates with existing systems and processes, reducing manual status reporting for key initiatives.
The ideal candidate is passionate about evolving portfolio and delivery practices, strengthening cross-functional partnerships, and maintaining a strong focus on business outcomes. Success in this role requires executive-level communication and facilitation skills, a data-driven mindset, strong change leadership aptitude, and a high degree of self-awareness and emotional intelligence. If you are looking for a career defining leadership opportunity that can transform how we work, this is the job for you.
Duties & Responsibilities
- Lean Portfolio Management (LPM): Establish and operationalize Lean Portfolio Management practices, driving better organization and governance around how we gather, prioritize, deliver, and measure initiatives globally
- Portfolio Governance : Establish and facilitate enterprise portfolio governance forums to review demand, sequence work, manage in‑flight reprioritization, and resolve cross‑portfolio dependencies and conflicts; Define roles, responsibilities, and decision rights to ensure clear ownership, accountability, and timely escalation
- Intake and Prioritization Process : Implement a standardized intake process and clear prioritization criteria to enable transparent trade-off discussions and improve funding decisions
- Portfolio Strategy and Alignment: Oversee all aspects of the technology portfolio to ensure alignment with corporate strategy, business priorities, technical roadmaps, and financial objectives while balancing innovation, operational stability, and risk
- Benefits Realization and ROI Analysis : Establish best practices and consistency around delivery metrics (predictability, quality, and business value delivery) and partner with key stakeholders (such as the CFO and global business leaders) to measure ROI and report on benefits realization
- Tooling and Integration: Lead the evaluation, selection, and implementation of a technology portfolio management tool, ensuring seamless integration with Agile backlog management tools and collaborating with other departments to align on a shared enterprise platform
- Stakeholder engagement : Partner with executive and senior leaders across business and technology gather input, communicate status and risks, and drive alignment cross-functionally
- Change Management and Adoption: Drive change management to embed a Lean/Agile mindset and drive adoption of new ways of working across the organization
- Continuous Improvement: Champion continuous improvement in portfolio processes, tools, and decision ‑ making to increase delivery predictability, transparency, and value realization
Qualifications, Skills, And Experience
- 15+ years of progressive leadership experience in technology portfolio management, strategy, planning, or operations
- Proven experience establishing and maturing enterprise portfolio management practices (e.g., intake, prioritization, governance, and transparency) and driving adoption across global stakeholders
- Deep understanding of Lean Portfolio Management and portfolio governance, including capacity-based prioritization and sequencing of work
- Demonstrated success designing and implementing standardized intake, prioritization, and evaluation processes
- Strong analytical skills and ability to deliver executive-level dashboards/insights on portfolio health, performance, and risk to inform decisions
- Excellent communication and stakeholder management skills, with the ability to influence and align senior leaders across business, technology and finance
- Experience with Enterprise Portfolio Management (EPM/PPM) platforms (such as Jira Align, Planview, Planisware) to support portfolio planning, prioritization, financial transparency, and executive decision making.
- Experience integrating EPM/PPM tools with agile backlog management tools for automated status tracking and timeline projections
- Demonstrated success leading organizational change and modernizing portfolio and delivery practices to improve transparency and outcomes
- Proven ability to lead with self-awareness and emotional intelligence, adapting style based on context and feedback while maintaining accountability
- Ability to challenge the status quo, operate with executive presence, and inspire followership
Preferred Qualifications
- Experience in insurance, financial services, or a similarly complex, regulated industry
- Program Management Certification such as PMP, PMI-ACP, CAPM, PgMP, PRINCE2 or similar
- Strong understanding of Agile, Lean, and hybrid software delivery models, including Scrum, Kanban, SAFe
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 $175,000 - $200,000 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.
NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.
