VP, Enterprise Initiatives & Project Execution

Vantage Risk Ltd.; Chicago (IL); Remote; USD 200,000 - 300,000; Full time

Benefits offered by this job

Performance-based bonus potential

Health & welfare benefits

Retirement plans with company match

Flexible time off plans

Highly flexible work environment

Job summary

Vantage Risk Ltd. seeks a dynamic Vice President, Enterprise Initiatives to drive cross-functional strategic priorities and enterprise transformation.

You will lead complex initiatives, partnering with business leaders to translate vision into measurable outcomes, accelerating growth in a fast-paced, entrepreneurial environment. As a key partner to senior leadership, you will promote operational rigor, champion iterative delivery, and ensure initiatives remain focused, adaptable, and aligned

Qualifications

• Bachelor’s degree or equivalent professional experience.
• 10+ years of progressive experience in project leadership.
• Experience in insurance or financial services preferred.
• Remote, virtual, or distributed workforce experience.
• Strong time management and negotiation skills.

Responsibilities

• Lead high-priority cross-functional initiatives from conception through execution and scaling.
• Orchestrate matrixed teams across Actuarial, Underwriting, Claims, IT, Compliance, and Operations.
• Translate strategies into concrete project roadmaps with milestones.
• Manage risk and change, identify risks early and build mitigation strategies.

Skills

Execution Focus

Influence Without Authority

Agile Leadership

Strategic Communication

Financial Acumen

Stakeholder management

Education

Bachelor’s degree or equivalent professional experience

Job description

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 intentional to deliver on our mission.