VP, Enterprise Initiatives & Project Execution

Vantage Group Holdings Ltd. (Vantage) was established in late 2020 as a re/insurance partner designed for the future. Driven by relentless curiosity, our team of trusted experts provides a fresh perspective on our clients’ risks. We add creativity to tech-enabled efficiency and robust analytics to address risks others avoid. Vantage provides specialty re/insurance through its operating subsidiaries in Bermuda and the U.S. Vantage has approximately 365 colleagues in both the United States and Bermuda.

We have offices in Chicago, IL, Norwalk, CT, West Hartford, CT, Washington, DC, Boston, MA, New York, NY, Atlanta, GA and Hamilton, Bermuda. Additionally, we are a highly geographically diverse workforce with colleagues based in 35 states and counting. We fully support work flexibility including remote and hybrid work arrangements.

We are seeking a dynamic, execution-focused Vice President, Enterprise Initiatives to drive Vantage's most critical cross-functional strategic priorities and enterprise transformation efforts. In this high-impact role, you will lead complex initiatives across the organization, partnering with business leaders to translate strategic vision into measurable outcomes. This role requires a collaborative leader who excels at influencing without direct authority, fostering shared accountability, and building alignment across diverse stakeholder groups.

The ideal candidate will champion operational rigor, embrace an iterative and results-oriented mindset, and help teams move quickly from concept to execution. Working closely with executive leadership, the Vice President, Enterprise Initiatives will accelerate business outcomes, promote continuous improvement, and ensure strategic initiatives remain focused, adaptable, and aligned with Vantage's long-term objectives. This is an exceptional opportunity for a highly motivated and versatile leader who thrives in a fast-paced, entrepreneurial environment and enjoys solving complex business challenges.

As a key partner to senior leadership, you will play a critical role in advancing enterprise-wide initiatives and contributing to the continued growth and success of Vantage. The base salary expectation for this role is between $200,000 and $300,000. Actual base salary for the selected candidate may be higher, commensurate with candidate experience and expectations. Additionally, Vantage offers its colleagues performance-based bonus potential, strong health & welfare benefits, retirement plans with company match, competitive time off plans, a highly flexible work environment, and much more.

• Enterprise Execution & Project Leadership Lead high-priority, cross-functional initiatives from conception through successful execution and scaling. Orchestrate virtual, matrixed teams across Actuarial, Underwriting, Claims, IT, Compliance, and Operations to ensure alignment and eliminate silos. Translate complex corporate strategies into concrete, actionable project roadmaps with clear milestones.
• Risk & Change Management:
  Identify operational, regulatory, or technical risks early and build mitigation strategies while leading organizational change management.
• Iterative Delivery & Agile Mentality Establish an iterative delivery framework that prioritizes speed-to-market and incremental value over rigid, traditional cycles. Embed a "fail fast, learn faster" culture, encouraging teams to test hypotheses, analyze setbacks, and pivot quickly without fear of blame. Implement robust post-mortem and feedback loops to ensure continuous learning and ongoing improvement are woven into every initiative.
• Accountability & Operational Rigor Build a culture of shared accountability, ensuring all cross-functional team members own their pieces of the project puzzle. Apply healthy project governance and rigor (KPI tracking, risk mitigation, resource management) without introducing unnecessary bureaucracy. Communicate progress, risks, and strategic outcomes clearly to executive leadership and board stakeholders.

• Bachelor’s degree or equivalent professional experience.
• 10+ years of progressive experience in project leadership, program management, or strategic execution, preferably within the insurance or financial services sector.
• Proven track experience in specialty insurance/reinsurance (e.g., Excess & Surplus lines, niche programs, cyber, or specialty liability) is highly preferred.
• Demonstrated success…