Chief of Strategic Initiatives & Transformation

This role is a senior enterprise leader and key advisor to the CEO, responsible for translating strategy into clear priorities, disciplined execution, and measurable value creation across HSB. The role drives strategic alignment, transformation delivery, and organizational effectiveness in support of HSB and Munich Re/Global Specialty Insurance (GSI) objectives.

The role is responsible for the following: converting CEO-level strategy into actionable initiatives with defined metrics and accountability; facilitating enterprise transformation and modernization across functions, platforms, processes, and operating models; strengthening governance, decision-making, and operating rhythm across the CEO Office and ELT; driving one-enterprise collaboration across HSB Group (HSB US, HSB UK, HSB Canada, Solomon, GEIS and Key External Partners); and cross collaboration with GSI and Munich Re.

Education and Experience:

• Bachelor’s degree required; MBA, CPCU, or advanced degree preferred.
• 15+ years of experience in strategy, operations, or executive leadership within (re)insurance, financial services, or innovation-driven organizations.
• Proven experience advising C-suite leaders and leading strategy, change, and transformation.
• Demonstrated experience building and leading high-performing teams in fast-paced, executive-facing environments.

Knowledge and Skills:

• Strong familiarity with HSB’s business model and market.
• Ability to drive fast, transparent strategic execution through clear accountability, decision rights, and operating cadence.
• Ability to identify and deliver measurable synergies across HSB Group and GSI.
• Deep knowledge of designing efficient operating models that enable strong cross-team collaboration.
• Ability to establish disciplined CEO Office governance and decision rhythm.
• Strong analytical, communication, and influence skills. Ability to communicate enterprise strategy clearly to drive alignment and focus
• Excellent change-management and continuous improvement mindset.
• Ability to navigate complex, matrixed organizations and manage multiple projects.
• Strong organization, time management, and attention to detail skills.
• Skilled at anticipating risks, identifying contingency plans, and determining future consequences.
• Excellent verbal and written communication skills, with ability to interact at all levels.

25-50% travel is required.

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 the most innovative products and services.   

We are an equal opportunity employer. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

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 accommodations 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.