VP, Enterprise Initiatives & Project Execution

Vantage Risk Companies•Chicago, IL
•$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 translate strategic vision into measurable outcomes, accelerate business results, promote continuous improvement, and keep initiatives aligned with Vantage’s long-term objectives. The Vice President will lead complex initiatives in a fast-paced, entrepreneurial environment, influencing teams without direct authority and fostering alignment and shared accountability. The role emphasizes operational rigor, iterative delivery, adaptability, and moving initiatives from concept through execution and scaling. Vantage supports flexible work arrangements, including remote and hybrid work.

Requirements

  • Bachelor’s degree or equivalent professional experience.
  • 10 or more years of progressive experience in project leadership, program management, or strategic execution.
  • Demonstrated success leading complex projects in 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, with the ability to interact effectively with a broad range of constituencies.
  • Strong financial acumen, stakeholder management, and conflict resolution skills.
  • Ability to influence 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.

Nice To Haves

  • Experience in the insurance or financial services sector.
  • Track record in specialty insurance or reinsurance, such as Excess & Surplus lines, niche programs, cyber, or specialty liability.

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 build alignment and eliminate silos.
  • Translate corporate strategies into actionable project roadmaps with clear milestones.
  • Identify operational, regulatory, and technical risks early; develop mitigation strategies and lead organizational change management.
  • Establish an iterative delivery framework that prioritizes speed to market and incremental value.
  • Encourage teams to test hypotheses, learn from setbacks, and pivot quickly without blame.
  • Implement post-mortems and feedback loops to embed continuous learning and improvement.
  • Foster 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.

Benefits

  • Performance-based bonus potential.
  • Health and welfare benefits.
  • Retirement plans with company match.
  • Competitive time-off plans.
  • Flexible work environment, including remote and hybrid arrangements.
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