Job Opportunity:

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 not a single-product ownership role. It 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.

The role operates across business leadership, underwriting, operations, technology, and platform stakeholders spanning multiple geographies and time zones, aligning organizational priorities into a coherent product portfolio strategy. This position is expected to balance immediate business opportunities with long-term platform sustainability and reusable capability development.

Success in this role requires strong people leadership, product judgment, strategic prioritization discipline, and the ability to build consensus among senior stakeholders around clear investment decisions and measurable business outcomes.

Duties & Responsibilities:

Product Strategy & Portfolio Direction

• 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

Portfolio Prioritization & Investment Governance

• 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

Stakeholder & Executive Alignment

• 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

Product Management Leadership

• 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

Product Outcomes & Performance

• 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

Product Operating Model & Governance

• 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

Qualifications, Skills, & Experience

• 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

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, MA is $160,000 to $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.