AVP, Strategy & Planning - Portfolio Management

Berkshire Hathaway Specialty Insurance•Boston, MA

23h•$175,000 - $200,000•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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

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