Fortitude Reinsurance Company Ltd. (Fortitude Re) is one of the world’s leading providers of legacy reinsurance solutions. They work with the world’s leading insurance companies to help them execute comprehensive, transformational solutions for legacy Life & Annuity and P&C lines. Fortitude Re manages a general account of approximately $111 billion across life, annuity, and property & casualty insurance products. The company takes a long-term view on growth and is proud to be backed by a consortium of sophisticated institutional investors led by The Carlyle Group and T&D Insurance Group. Incorporated under the laws of Bermuda on January 1, 2017, Fortitude Re’s roots in the insurance industry and the experience of their leadership go back many decades. Fortitude Re’s leadership team has an average industry tenure of over 20 years, and an impressive track record of successfully managing the most complex legacy liabilities. Their deep insurance experience and proprietary risk modeling capabilities allow them to structure bespoke transactions that benefit both insurance companies and their policyholders. Fortitude Re continues to strengthen its ability to pursue further growth and provide innovative solutions for the global insurance industry. Click here for more information about Fortitude Re.

The VP, Program & Transformation Delivery is a senior leadership role responsible for overseeing a portfolio of cross-functional initiatives that directly support the company’s strategic objectives. This leader will manage a team of program and project managers, ensuring initiatives are prioritized, coordinated, and executed with excellence. This leader will be a champion for process reengineering and automation, helping the organization rethink how work gets done and supporting initiatives that introduce automation and AI solutions that streamline operations, improve accuracy, and deliver long-term efficiency. This role requires a consulting mindset — able to think strategically, engage senior executives with confidence, and dive into execution when needed, thriving in a hands-on leadership environment where influence, alignment, and delivery are equally critical.

What You Will Do

Leadership & Oversight

Lead, mentor, and develop a team of program and project managers.
Oversee program delivery, ensuring accountability for scope, schedule, budget, and outcomes.
Utilize the PMO governance frameworks, tools, and standards owned by the Governance team; collaborating and providing feedback for refinement.

Strategic Alignment & Transformation

Partner with the Head of Transformation and executives to define program vision and priorities in alignment with corporate strategy.
Translate strategic objectives into actionable roadmaps with measurable outcomes.
Act as a bridge between IT and business, ensuring technology initiatives deliver tangible business value.
Drive process reengineering efforts to simplify, standardize, and optimize workflows.
Identify opportunities to implement basic automation and AI solutions to improve efficiency, accuracy, and decision-making.

Stakeholder Engagement & Influence

Serve as the trusted advisor to senior leaders, ensuring transparent communication of program progress, risks, and outcomes.
Facilitate cross-functional alignment and collaboration
Proactively manage risks, resolve conflicts, and enable executive decision-making.

Execution & Continuous Improvement

Guide the delivery of large-scale, interdependent initiatives, ensuring consistent adoption of standards and methodologies.
Monitor KPIs and success metrics to measure impact and drive accountability.
Foster a culture of agility, collaboration, and continuous improvement.
Promote innovation by encouraging the use of new tools and techniques, including automation and AI.

What You Will Have

Undergraduate degree required; MBA or equivalent advanced degree preferred.
12+ years of progressive program/portfolio leadership experience, including leading teams of program/project managers.
Prior consulting experience (Big 4, boutique strategy, or equivalent) strongly preferred; consulting mindset essential.
Demonstrated ability to partner with C-suite and senior executives, influencing at the highest levels.
Proven success driving cross-functional programs that bridge technology and business needs.
Demonstrated experience leading programs that use Agile or hybrid delivery models (Scrum, Kanban, SAFe, or similar)
Hands-on experience with program and project management methodologies; PMP, Prince2, or equivalent certification strongly preferred.
Familiarity with process reengineering, automation, AI, or digital transformation initiatives; able to deliver pragmatic solutions at scale.
Exceptional communication, facilitation, and negotiation skills; able to manage conflict and drive alignment.
Insurance industry knowledge (Life & Annuities preferred) is a plus.
A self-starter who thrives in a fast-paced, entrepreneurial environment, comfortable operating at both the strategic and tactical levels.

The base salary range for this role is listed below and will be commensurate with candidate experience. Pay ranges for candidates may differ based on the cost of labor in that location. In addition to base salary, all employees are eligible for an annual bonus based on company and individual performance as well as a generous benefits package.

Base Salary Range: $190,000 USD - $210,000 USD

At Fortitude Re, our strength has always come from our people. Our success is deeply rooted in our ability to embrace the unique attributes, perspectives and experiences of every individual within our company. Fostering a culture of inclusion and belonging where everyone—regardless of background, race, religion, sexual orientation or gender identity—feels valued and respected is a foundation of our culture.

We are committed to being an equal opportunity employer and evaluate qualified applicants without regard to race, color, religion, sex, pregnancy (including childbirth, lactation and related medical conditions), national origin, age, physical and mental disability, marital status, sexual orientation, gender identity, gender expression, genetic information (including characteristics and testing), military and veteran status, diversity of thought and any other characteristic protected by applicable law.

To all recruitment agencies: Unless you have been requested to work on this position, or other positions with Fortitude Re, please do not forward any resumes to Fortitude Re employees. Fortitude Re is not responsible for any fees related to unsolicited resumes.

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