VP, Enterprise Initiatives & Project Execution

Vantage Risk•Chicago, IL

10d

About The Position

Vantage is seeking an execution-focused Vice President, Enterprise Initiatives 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, build alignment and shared accountability across stakeholder groups, and move initiatives from concept through execution. The successful candidate will promote operational rigor, continuous improvement, iterative delivery, and adaptability in a fast-paced, entrepreneurial environment. The Vice President will lead complex enterprise initiatives, coordinate matrixed teams across multiple functions, manage risks and organizational change, and communicate progress and outcomes to executive leadership and board stakeholders. The position is a key partner to senior leadership in advancing enterprise-wide initiatives and supporting Vantage’s growth and long-term objectives. The stated base salary expectation is $200,000–$300,000; the selected candidate’s base salary may be higher depending on 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.
At least 10 years of progressive experience in project leadership, program management, or strategic execution.
Proficiency in time management, leadership, organizational influence, and project management.
A proven track record of achieving results and demonstrating collaboration, teamwork, problem solving, and negotiation skills.
Strong interpersonal and communication skills, including the ability to interact effectively with a broad range of constituencies.
Strong financial acumen, stakeholder management, and conflict resolution skills.
Ability to influence and motivate cross-functional teams without direct authority.
Ability to distill complex project data into strategic insights for C-suite executives.

Nice To Haves

Experience in the insurance or financial services sector.
Experience in specialty insurance or reinsurance, such as Excess & Surplus lines, niche programs, cyber, or specialty liability.
Success leading complex projects in a fully remote, virtual, or highly distributed workforce.
Understanding of iterative, lean, or Agile methodologies applied to business operations.

Responsibilities

Lead high-priority cross-functional initiatives from conception through execution and scaling.
Coordinate virtual, matrixed teams across Actuarial, Underwriting, Claims, IT, Compliance, and Operations to align stakeholders and eliminate silos.
Translate corporate strategies into actionable project roadmaps with clear milestones.
Identify operational, regulatory, and technical risks and develop mitigation strategies.
Lead organizational change management.
Establish an iterative delivery framework that emphasizes speed to market and incremental value.
Encourage teams to test hypotheses, learn from setbacks, and pivot quickly.
Implement post-mortems and feedback loops to support continuous learning and improvement.
Build shared accountability among cross-functional team members.
Apply project governance, KPI tracking, risk mitigation, and resource management without unnecessary bureaucracy.
Communicate progress, risks, and strategic outcomes to executive leadership and board stakeholders.