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About the Role

The Director, Product Management is a senior leadership role accountable for bringing structure, clarity, and alignment to an evolving product portfolio across the S|2 platform. This role leads a team of Product Managers and Product Owners, builds consensus across senior stakeholders, and ensures the S|2 product portfolio delivers measurable business value through a cohesive, well-sequenced roadmap. This is a portfolio and people leadership position, responsible for determining what problems the organization should solve, why those problems matter, and how investments should be prioritized to maximize long-term business value and platform scalability.

Responsibilities

Owns product portfolio strategy across the S|2 platform and SME product ecosystem
Decides product investment priorities based on business value, operational impact, customer outcomes, and platform strategy
Owns product roadmap direction, business investment priorities, and portfolio-level sequencing decisions
Defines measurable business outcomes and success criteria for product investments
Evaluates market opportunities, operational pain points, customer needs, and competitive dynamics to guide portfolio direction
Balances short-term business needs against long-term platform scalability and reuse objectives
Owns intake, prioritization, and tradeoff decisions across competing initiatives
Decides priority alignment across business stakeholders, underwriting teams, and platform capabilities
Evaluates investment requests against strategic alignment, operational value, implementation complexity, and organizational capacity
Maintains alignment between business priorities and platform evolution strategy
Establishes clear decision frameworks for roadmap prioritization and investment sequencing
Drives alignment across underwriting, operations, claims, technology, and executive stakeholders
Represents product strategy, priorities, and investment rationale in executive and steering committee discussions
Facilitates leadership alignment around roadmap priorities and investment tradeoffs
Partners with Engineering leadership to align platform architecture direction with product strategy
Ensures stakeholders understand roadmap tradeoffs, sequencing decisions, and expected business outcomes
Builds, leads, and develops a high-performing product team, fostering strong product judgment, stakeholder management skills, and outcome-driven thinking
Owns hiring, onboarding, performance management, and career progression for the product team
Establishes standards for backlog quality, requirements clarity, outcome measurement, and product operating discipline
Drives operational maturity across product management practices as the platform organization scales
Owns business outcome accountability for the product portfolio
Defines and monitors outcome metrics related to adoption, operational efficiency, underwriting effectiveness, and platform utilization
Uses product performance data to adjust investment priorities and roadmap direction
Ensures product decisions remain grounded in measurable business impact rather than stakeholder preference alone
Establishes a clear product management operating model that drives consistency, accountability, and outcome focus across the product team
Elevates organizational decision quality through disciplined prioritization frameworks and investment governance
Ensures product investments remain aligned to measurable business outcomes and long-term platform strategy
Reinforces a culture of roadmap discipline and business value realization across the product organization

Requirements

10+ years of experience in product management, product strategy, or portfolio leadership roles
Proven experience managing complex product portfolios in platform-oriented technology organizations
Strong strategic prioritization and investment decision-making capabilities
Experience aligning business, operational, and technology stakeholders across large initiatives
Demonstrated ability to translate market and operational insights into actionable product strategies
Strong executive communication and stakeholder influence skills
Proven ability to lead, coach, and develop Product Managers and Product Owners in a people leadership capacity
Strong understanding of Agile delivery models and modern product operating practices
Experience working within insurance, financial services, or regulated industries preferred
Ability to balance business urgency with long-term platform sustainability and operational scalability
Strong analytical thinking, organizational judgment, and outcome-oriented decision-making capabilities
Comfortable collaborating across multiple time zones and geographies

Skills

Product Strategy
Portfolio Leadership
Strategic Prioritization
Investment Decision-Making
Stakeholder Alignment
Executive Communication
Stakeholder Influence
People Leadership
Agile Delivery Models
Product Operating Practices
Analytical Thinking
Organizational Judgment
Outcome-Oriented Decision-Making

Location

Boston, MA

Work Type

Full-time

Experience Level

10+ years of experience

Salary/Compensations

$160,000 to $200,000

Benefits

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

About the Company

Berkshire Hathaway Specialty Insurance (BHSI) is a strategic and trusted insurance partner providing a broad range of commercial property, casualty, and specialty insurance solutions to customers and brokers around the world.
Part of Berkshire Hathaway’s insurance operations, we combine a top-rated balance sheet, disciplined execution, and a global team known for strong capability and strong character.
We are building a scalable digital platform to support long-term growth across Small & Medium Enterprise (SME) insurance products and operations.
Our operating model emphasizes reusable platform capabilities, disciplined execution, clear accountability, and durable technology foundations that accelerate speed to market.
We are a values-based organization where respect, integrity, excellence, collaboration, and passion define how we operate.
We value diversity of background, experience, and perspective, and we foster an environment where teammates are expected to contribute meaningfully, operate with accountability, and continuously raise the quality of the organization around them.