Head of Underwriting Spec Portfolio

Role Description

The Head of Portfolio Underwriting leads a group of Underwriters and collaborates with Product Managers for guidance on product directives and execution of client initiatives. This role is accountable for the profitable growth of all Alternative Markets Portfolio business.

The role works with the Alternative Markets Leadership Team, Product Management and Group Corporate Underwriting (GCU) to implement and communicate underwriting policies and procedures and provide underwriting expertise to the Portfolio Underwriting staff for all product offerings. Ensures policies, procedures and insurance documentation are compliant with established corporate, regulatory, and legal requirements.

This role requires close collaboration with internal stakeholders to communicate HSB’s value proposition, ensure strong product performance, and deliver excellent client experience. The Head of Underwriting will have underwriting binding authority via their letter of authority.

Key Responsibilities

• Lead, develop, and retain a high-performing underwriting team through coaching, performance management, and talent development
• Establish clear expectations for portfolio ownership, monitoring cadence, client engagement, and documentation standards
• Set portfolio growth targets and partner with leadership, Finance, and stakeholders to execute product-specific growth strategies
• Own delivery of portfolio financial results including growth, profitability, and underwriting gains
• Analyze portfolio performance to identify opportunities, risks, and emerging trends impacting pricing and underwriting strategy
• Provide underwriting expertise, guidance, and escalation support for complex risks, referrals, and coverage decisions
• Ensure adherence to underwriting guidelines, regulatory requirements, and internal governance standards
• Drive continuous improvement across underwriting processes, systems, and portfolio execution
• Partner with Product Managers and internal stakeholders to influence product strategy and investment decisions
• Lead change management initiatives related to product, process, and technology enhancements

Qualifications

• Bachelor’s degree or equivalent work experience in Business Administration, Risk Management, Marketing, Product Management, or a related field
• 7+ years of underwriting or relevant insurance experience, preferably with commercial or property exposure
• Experience in portfolio management, underwriting strategy, or product-driven insurance environments
• Demonstrated experience leading and developing teams with strong mentoring and leadership capabilities
• Strong analytical and financial acumen with experience managing P&L and influencing business results
• Experience driving strategy and execution in a complex insurance or product environment
• Advanced degree or professional designation (e.g., CPCU) preferred

Knowledge & Skills

• Strong interpersonal and relationship management skills
• Ability to influence stakeholders and present effectively to executive-level audiences
• Customer-centric mindset with strong understanding of client needs and expectations
• Strategic thinker with the ability to drive innovation and continuous improvement
• Strong decision-making and problem-solving skills in complex underwriting environments
• Ability to collaborate cross-functionally and drive organizational alignment
• Strong communication skills (verbal and written) with ability to tailor messaging to different audiences
• Highly proactive with strong initiative and ability to manage ambiguity
• Ability to translate data-driven insights into actionable underwriting strategies
• Strong organizational awareness and ability to navigate and influence complex organizations

Benefits

• The salary range for this position is $177,000 - $280,000, plus opportunity for company bonus.
• The company provides a variety of benefits to employees, including health insurance coverage, an employee wellness program, life and disability insurance, a retirement savings plan, paid holidays and paid time off (PTO).