VP, Enterprise Initiatives & Project Execution

About the Company

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.

About the role :

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.

Responsibilities & Accountabilities :

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.

Ideal Candidate Profile :

• 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 leading complex projects within a fully remote, virtual, or highly distributed workforce.
• Demonstrate a high proficiency in time management, leadership, organizational influence, and project management skills.
• Have a proven track record of results achievement, collaboration, teamwork, problem solving, and negotiation skills.
• Have strong interpersonal and communication skills and the ability to effectively interact with a broad spectrum of constituencies.

Competencies :

• Execution Focus : A bias for action and a proven track record of getting things across the finish line in a fast-paced environment.
• Influence Without Authority : Exceptional interpersonal skills to motivate and align diverse, cross-functional teams that do not report to you directly.
• Agile & Adaptive Leadership : Comfort with ambiguity and a strong understanding of iterative, lean, or Agile methodologies applied to business operations (beyond just software development).
• Strategic Communication : Ability to distill complex project data into high-level strategic insights for C-suite executives.
• Skills : Strong financial acumen, stakeholder management, and conflict resolution.

Vantage Values

Do What’s Right – be a force for good, for our customers, shareholders, colleagues, industry, and communities.
Be Relentlessly Curious – ask questions, listen to understand, challenge the status quo, look for ways to say YES, drive innovation, be opportunistic and disciplined.
We’re Better Together – collaborate, be inclusive, supportive, respectful, and humble, be a trusted partner internally and externally.
Be Transparent – in who you are, what you think, and how you work, seek, and provide alternative points of view, be true to yourself.
Make A Difference – focus on impact, embrace technology, leverage data and analytics as critical assets, act intentionally to deliver on our mission.

We value diversity and are committed to creating an inclusive environment for all employees. At Vantage, we strive to build and foster a culture where inclusiveness is ingrained, not just an initiative. All colleagues support building an inclusive environment where employees feel empowered to share their experiences and ideas to foster an environment which encourages you to "Be You!" We are proud to be an equal opportunity employer.

In connection with our business, Vantage may collect and process your personal data. For further information regarding how we use this data, please see our online privacy notice at Vantage Recruiting Privacy Notice.

ADA Notice: All applications shall be submitted online through our applicant tracking system. Candidates needing reasonable disability accommodation to enable them to apply and/or fully participate in the selection process are encouraged to email View email address on aiapply.co with the subject Candidate ADA Request detailing their needs. Please note the above email box is for candidates needing reasonable disability accommodation only, emails submitting resumes will not be considered and those seeking application status updates will go unanswered.