Vice President, Enterprise

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.

• 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.
• 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.

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

• 12–15+ years leading large-scale change initiatives.
• 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.

• 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.

• Experience in regulated industries (e.g., financial services, insurance, MGA)
• Demonstrated digital and process transformation capabilities

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

• PROSCI (Change Management)
• PMP (Project Management Professional)

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.

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…