VP, Enterprise Initiatives & Project Execution

Vantage Group Holdings • Chicago, IL

10d • $200,000 - $300,000

About The Position

Vantage Group Holdings Ltd. is seeking a dynamic, execution-focused Vice President to drive critical cross-functional strategic priorities and enterprise transformation efforts. The role leads complex initiatives across the organization, partnering with business leaders to turn strategic vision into measurable outcomes. It calls for a collaborative leader who can influence without direct authority, foster shared accountability, and build alignment across diverse stakeholder groups while promoting operational rigor and iterative, results-oriented execution.

Working closely with executive leadership, the VP will accelerate business outcomes, promote continuous improvement, and keep strategic initiatives focused, adaptable, and aligned with Vantage’s long-term objectives. The position is suited to a versatile leader who thrives in a fast-paced, entrepreneurial environment and enjoys solving complex business challenges. Vantage has approximately 365 colleagues in the United States and Bermuda, supports remote and hybrid work arrangements, and offers a base salary expectation of $200,000 to $300,000. The selected candidate’s base salary may be higher depending on experience and expectations.

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 in a fully remote, virtual, or highly distributed workforce.
• High proficiency in time management, leadership, organizational influence, and project management.
• Proven track record of achieving results, collaboration, teamwork, problem solving, and negotiation.
• Strong interpersonal and communication skills, with the ability to interact effectively with a broad range of constituencies.
• Ability to influence and align diverse 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.
• Proven 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 ensure 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 over rigid traditional cycles.
• Encourage teams to test hypotheses, learn from setbacks, and pivot quickly without fear of blame.
• Implement post-mortem and feedback loops to support continuous learning and improvement.
• Build shared accountability so cross-functional team members own their project responsibilities.
• 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.
• Highly flexible work environment, including support for remote and hybrid arrangements.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive