Vice President, Enterprise Change

Job Summary:

At Tokio Marine Highland (TMH) we are strengthening our enterprise delivery capability to support sustainable growth, sharper strategic alignment and disciplined execution. As the business scales in complexity and ambition, we are embedding a clear governance framework, robust investment prioritization and consistent oversight to ensure initiatives deliver measurable business value.

The VP, Enterprise Change reports to the COO and leads the BAU change function. It is accountable for ensuring that strategic initiatives are prioritized, governed and executed in line with enterprise objectives. The role plays a critical part in embedding a transparent, repeatable delivery model that enhances executive visibility, improves decision quality and drives outcomes at pace and scale.

Key Responsibilities:

Enterprise Change & Portfolio Leadership

• Partner with Executive Leadership to define and advance the multi-year change agenda, translating strategic priorities into sequenced roadmaps, investment plans, and disciplined portfolio execution aligned to business and financial objectives.
• Lead the enterprise change portfolio, establishing clear prioritization, governance, capacity planning, and performance transparency to ensure initiatives are properly sequenced, resourced, and delivered at a sustainable pace.
• Advise the Executive Leadership Team on investment trade-offs, risks, dependencies, and benefit realization, ensuring strong PMO standards, financial controls, and outcome accountability.

Organizational Change & Value Realization

• Define and embed a consistent change management methodology, leading communications, stakeholder engagement, readiness, and sustained adoption across the enterprise.
• Establish outcome-based KPIs and value tracking to ensure initiatives deliver measurable commercial impact, operational efficiency, and strategic advantage, with clear business ownership of benefits.

Team Leadership & Capability Building

• Build and lead a high-performing Change team, strengthening enterprise delivery capability, maturity, and a culture of accountability, transparency, and execution excellence.

Experience and Skills Required:

• 12–15+ years leading large-scale change initiatives.
• Experience in the insurance industry
• Proven experience building or leading a change function.
• Demonstrated success delivering complex, cross-functional programs from strategy through implementation.
• Executive presence with strong influencing skills at C-suite level.

Core Competencies

• Strategic Portfolio & Value Delivery: Translate strategy into executable roadmaps; lead enterprise portfolio management, financial oversight, benefits realization, and risk governance.
• Organizational Change Leadership: Drive enterprise change, stakeholder engagement, and sustained adoption through clear executive communication and influence.
• Enterprise Stakeholder Influence: Build alignment across senior leaders through strong judgment, credibility, and organizational awareness.
• Executive Decision-Making: Demonstrate clarity, discernment, and sound escalation judgment in complex, high-impact environments.
• Composed Leadership: Lead with executive presence, emotional intelligence, and resilience under pressure.

Preferred Qualifications

• Demonstrated digital and process transformation capabilities

Required Education:

• Bachelor’s or Master’s degree in Business Administration, Organizational Psychology, Human Resources Management, or a related field.

Preferred Certifications

• PROSCI (Change Management)
• PMP (Project Management Professional)
• SAFe (Lean Portfolio Management)

Additional Job Details:

This hybrid position is based in Chicago, IL, with 2-3 days in office each week.

The pay range for this role is $155,800 - $202,600. This range reflects a good faith estimate of pay at the time of posting. Actual compensation will be determined based on factors such as experience, skills, knowledge, education, and internal pay equity.

About Tokio Marine Highland

Tokio Marine Highland Insurance Services (TMH) is a leading property and casualty underwriting agency. We offer a broad suite of tailored specialty risk management solutions, including private flood, fine art and lender-placed products. At TMH, it’s all about our clients. Nationwide, our customers rely on our trusted, industry-leading coverages, supported by compliance expertise, superior claims management and the highest caliber of service.

Founded in 1962, TMH is a wholly owned company of Tokio Marine Kiln, one of the largest carriers in the Lloyd’s of London insurance market and a member of the Tokio Marine Group. TMH has operating centers in Chicago, Il, Frisco, Texas, Miami, Fla., and South Pasadena, Calif.

If you’re looking to advance your career, TMH is the perfect professional home. At TMH, you’ll have a chance to innovate with the world’s leading businesses, put your expertise into action on major projects, and work on game-changing initiatives. You’ll also make long-lasting professional connections through sharing different perspectives, and you’ll be inspired by the best.

Tokio Marine Highland, LLC (TMH) is an Equal Opportunity Employer. TMH’s success depends heavily on the effective utilization of qualified people, regardless of their race, ancestry, religion, color, sex, national origin, sexual orientation, gender identity and/or expression, disability, veteran status, or any characteristic protected by law. As a company, we adhere to and promote equal employment opportunities for all.

Consistent with the Americans with Disabilities Act (ADA) and applicable state and local laws, it is TMH’s policy to provide reasonable accommodation when requested by qualified individuals with disabilities during the recruitment process, unless such accommodation would cause an undue hardship. To make an accommodation request, please contact humanresources@tmhighland.com.