Head Of Retail Operations Jobs in Springfield, MA

HSB, a Munich Re company, is a specialty insurer and risk solutions provider known for its industry-leading equipment breakdown coverage. We combine deep engineering expertise with cutting-edge technology to help clients prevent loss and ensure operational resilience. Our offerings include equipment breakdown insurance and other specialty coverages (cyber, EPLI, service line, home appliances), along with a suite of risk management services powered by 1,200 engineers and inspectors, IoT sensors, AI, and predictive analytics. HSB is redefining insurance by focusing on prevention-not just protection.

This role is part of our Custom Risk Solutions division, which focuses on the fast-growing segment of the P&C market, including E&S carriers, large commercial risk writers, MGAs, programs, Lloyds, and pools. The division manages over 100 client relationships and has ambitious growth goals.

Open to all HSB/Munich Re Offices + Remote Options

About the Role

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

At The Hartford Steam Boiler, a subsidiary of Munich Re, we see Diversity and Inclusion as a solution to the challenges and opportunities all around us. Our goal is to foster an inclusive culture and build a workforce that reflects the customers we serve and the communities in which we live and work. We strive to provide a workplace where all of our colleagues feel respected, valued and empowered to achieve their very best every day. We recruit and develop talent with a focus on providing our customers with the most innovative products and services.   

We are an equal opportunity employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status.  The work environment characteristics, and any physical and mental requirements described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodation may be made to enable individuals with disabilities to perform the essential functions.

This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee.  Other duties, responsibilities and activities may change or be assigned at any time with or without notice.

The Company is open to considering candidates in numerous locations, including California.  The salary range posted below applies to the Company's Hartford CT location.

   The salary range for this position is $ 177,000 - $280,000, plus opportunity for company bonus.  In addition, 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).

   The salary estimate displayed represents the typical salary range of candidates hired. Factors that may be used to determine your actual salary may include your specific skills, how many years of experience you have and comparisons to other employees already in this role. Most candidates will start in the bottom half of the range.