VP, Enterprise Initiatives & Project Execution

Vantage Risk Companies•Washington, DC

11d•$200,000 - $300,000

About The Position

Vantage Group Holdings Ltd. is seeking an execution-focused Vice President to lead critical cross-functional strategic priorities and enterprise transformation efforts. The role partners with business and executive leaders to turn strategic vision into measurable outcomes, build alignment across stakeholder groups, and promote shared accountability. The successful candidate will help advance enterprise-wide initiatives, accelerate business outcomes, foster continuous improvement, and keep initiatives aligned with Vantage’s long-term objectives in a fast-paced, entrepreneurial environment. The position leads complex initiatives from conception through execution and scaling, coordinating virtual, matrixed teams across Actuarial, Underwriting, Claims, IT, Compliance, and Operations. It translates corporate strategy into actionable roadmaps, manages operational, regulatory, and technical risks, and leads organizational change. The role also establishes iterative delivery practices, encourages experimentation and learning, applies appropriate project governance and operational rigor, and communicates progress, risks, and outcomes to executive and board stakeholders. Vantage has approximately 365 colleagues in the United States and Bermuda, with colleagues in 35 states and offices in Chicago, Norwalk, West Hartford, Washington, Boston, New York, Atlanta, and Hamilton, Bermuda. The company supports remote and hybrid work arrangements. The stated base salary expectation is $200,000–$300,000, with possible higher pay based on candidate experience and expectations. Vantage also offers performance-based bonus potential, health and welfare benefits, retirement plans with company match, competitive time-off plans, and a highly flexible work environment.

Requirements

Bachelor’s degree or equivalent professional experience.
10+ years of progressive experience in project leadership, program management, or strategic execution.
Demonstrated success leading complex projects within a fully remote, virtual, or highly distributed workforce.
High proficiency in time management, leadership, organizational influence, and project management.
Proven results achievement, collaboration, teamwork, problem-solving, and negotiation skills.
Strong interpersonal and communication skills, including the ability to interact effectively with a broad spectrum of constituencies.
Execution focus and a track record of delivering outcomes in a fast-paced environment.
Exceptional interpersonal skills and ability to motivate and align cross-functional teams without direct authority.
Comfort with ambiguity and understanding of iterative, lean, or Agile methodologies applied to business operations.
Ability to distill complex project data into strategic insights for C-suite executives.
Strong financial acumen, stakeholder management, and conflict-resolution skills.

Nice To Haves

Experience in the insurance or financial services sector is preferred.
Proven track record in specialty insurance or reinsurance, such as Excess & Surplus lines, niche programs, cyber, or specialty liability, is highly preferred.

Responsibilities

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.
Identify operational, regulatory, or technical risks early and develop mitigation strategies while leading organizational change management.
Establish an iterative delivery framework that prioritizes speed to market and incremental value over rigid traditional cycles.
Encourage teams to test hypotheses, analyze setbacks, and pivot quickly without blame.
Implement post-mortems and feedback loops to embed continuous learning and ongoing improvement in initiatives.
Build a culture of shared accountability among cross-functional team members.
Apply project governance and rigor, including KPI tracking, risk mitigation, and resource management, without unnecessary bureaucracy.
Communicate progress, risks, and strategic outcomes clearly to executive leadership and board stakeholders.