Business Transformation Strategist

May require up to 20% travel to the Milwaukee or Merrill, WI office. 

 

BASIC PURPOSE:

 

We are seeking an experienced and highly capable business operations leader to support enterprise-wide transformation initiatives within our Property & Casualty (P&C) organization. This individual will play a critical role in advancing operational effectiveness, enhancing policy lifecycle processes, facilitating systems and vendor integrations, and driving strong execution across complex initiatives. This role requires deep knowledge of the P&C regulatory environment, strong commercial lines expertise, and the ability to operate with significant responsibility while influencing cross-functional teams in a matrix environment.

 

PRIMARY JOB RESPONSIBILITIES:

 

• Identify high-visibility, high-impact business transformation initiatives spanning underwriting, operations, systems, and regulatory compliance.
• Serve as a strategic advisor to the SVP and executive team.
• Drive improvements across the full policyholder lifecycle, including quoting, underwriting, issuance, servicing, billing, claims interfaces, and renewals.
• Oversee or coordinate activities related to multiple policy administration systems, including configuration, workflow design, rules management, and system enhancements.
• Partner closely with IT, product, underwriting, operations, and vendor partners to ensure cohesive systems integration and smooth implementation of enterprise initiatives.
• Ensure regulatory compliance across multiple states by maintaining a deep and current understanding of state-specific rules, filing requirements, advisory bureau changes, and operational impacts.
• Manage and influence project teams in a matrixed environment without direct supervisory authority, ensuring accountability, alignment, and delivery of outcomes.
• Evaluate vendor performance, negotiate scope, and coordinate deliverables to ensure successful operational results.
• Develop and deliver executive-level presentations, reporting, and recommendations to senior leadership.

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REQUIRED QUALIFICATIONS:

 

• Minimum 10 years of experience in the Property & Casualty insurance industry.
• At least 7 years of experience specifically in Commercial Lines insurance.
• Demonstrated experience working with multiple policy administration systems, including hands-on configuration, rules development, workflow optimization, or system design.
• Strong knowledge of the multi-state regulatory environment across commercial insurance; experience with filings, compliance, and regulatory interpretation is highly preferred.
• Deep understanding of the policyholder lifecycle, including system touchpoints, operational dependencies, and compliance considerations.
• Experience with systems integration projects, cross-platform workflows, data movement, and vendor system connectivity.
• Proven ability to lead through influence in a matrix environment, driving outcomes without direct reports.
• Experience in vendor management, including evaluation, negotiation, and ongoing oversight.
• Exceptional communication, executive presence, and stakeholder management skills.

 

PREFERRED QUALIFICATIONS:

 

• Experience with enterprise transformation initiatives or large-scale modernization efforts.
• Knowledge of underwriting operations, digital workflow tools, or automation strategies.
• Experience collaborating with technical teams (IT, architecture, data).

 

 

WORK ENVIRONMENT:

 

• Office environment.

 

CHARACTERISTICS FOR SUCCESS:

 

• Strategic thinker with strong operational instincts.
• Comfortable owning large, complex responsibilities with minimal guidance.
• Able to navigate ambiguity and drive clarity across diverse stakeholders.
• Highly collaborative and adept at building trust across teams and leadership levels.
• Results-oriented with a bias for action.