VP, Head of Technology Enablement

About the Company

Vantage Group Holdings Ltd. (Vantage) was established in late 2020 as a re/insurance partner designed for the future. Driven by relentless curiosity, our team of trusted experts provides a fresh perspective on our clients’ risks. We add creativity to tech-enabled efficiency and robust analytics to address risks others avoid. Vantage provides specialty re/insurance through its operating subsidiaries in Bermuda and the U.S.

Vantage has approximately 365 colleagues in both the United States and Bermuda. We have offices in Chicago, IL, Norwalk, CT, West Hartford, CT, Washington, DC, Boston, MA, New York, NY, Atlanta, GA and Hamilton, Bermuda. Additionally, we are a highly geographically diverse workforce with colleagues based in 35 states and counting. We fully support work flexibility including remote and hybrid work arrangements. About the role: Vantage is seeking a Head of Technology Enablement to lead a portfolio of underwriting, operational, and technology build and transformation initiatives, serving as the connective layer between our underwriting business units and Data, Analytics & Technology organization (DA&T). Reporting to the CUO, UW Operations, you will drive evaluation, prioritization, definitions and execution of new technology initiatives to support and enable Vantage’s businesses. This is a builder and developer role: because Vantage's technology foundation was established in 2020 rather than inherited from decades of legacy infrastructure, you'll have latitude to partner with DA&T to evaluate, prioritize and continually evolve best-in-class systems rather than work around outdated ones. You will establish and lead a structured project governance and intake framework, spearhead executive steering committee reviews, and manage the integration of in-house and vendor systems across underwriting, operations, actuarial, and finance. You will also manage a team that owns core operational systems including submissions processing, underwriting premium systems, producer and document management systems, and customer management systems. The base salary expectation for this role is between $225,000 and $285,000. Additionally, Vantage offers its colleagues performance-based bonus potential, strong health & welfare benefits, retirement plans, competitive time off plans, a highly flexible work environment, and much more. Responsibilities & Accountabilities: Lead a portfolio of underwriting, operational, and technology transformation initiatives, driving scalability and alignment across functional domains. Serve as the primary bridge between underwriting businesses, operations, and DA&T across major projects and initiatives, ensuring the pieces connect end to end without owning day-to-day project delivery. Establish and own a structured project governance and intake framework for evaluating new project requests, including impacts, dependencies, risks, and stakeholder engagement. Spearhead executive steering committee reviews to facilitate high-level decision-making, risk mitigation, and strategic alignment. Partner with executive leadership to develop and execute a technology and operations enablement roadmap that supports business growth, efficiency, and scalability. Assess, prioritize, monitor and report on the integration of in-house and vendor systems, ensuring coordination across DA&T, underwriting, operations, actuarial, and finance. Translate business needs into practical technology solutions and translate technical constraints back into terms business stakeholders can act on. Promote, support, and monitor business usage of technology solutions and measure the business impact. Lead data stewardship practices across operational systems to ensure data integrity and usability for downstream business and technology initiatives. Manage and develop a team spanning onshore and offshore resources, delegating operational ownership to build team capacity. Lead the redesign of future-state processes, hand-offs, and decision points as new data, analytics, and technology capabilities are introduced so insights/data/systems are integrated with maximum impact. Serve as a cross-functional subject matter expert on how the organization's systems, teams, and processes connect from front-line operations to executive strategy, and flag structural or resourcing risks to leadership proactively. Ideal Candidate Profile: Bachelor’s degree or equivalent professional experience required. 15+ years in insurance operations, business operations, or technology enablement/digital transformation leadership, ideally within commercial lines or a related carrier environment. Proven track record leading enterprise-wide portfolios of underwriting, financial, and operational transformation initiatives across multiple regions or business units. Experience establishing project governance and intake frameworks, including executive steering committee facilitation. Deep working knowledge of underwriting and policy & claims administration systems (e.g., Majesco, Guidewire, Duck Creek, Instec, or similar), producer/document management systems, and customer management system platforms. Deep knowledge of commercial underwriting workflows from submission and triage through bind, including key decision points and hand-offs. Experience designing future-state workflows that embed AI, Data Science models, and new technology to increase operational effectiveness and/or enhance decisions. Strong project management, change management, and communication skills, able to operate fluently in both business and technical conversations. Strong consensus building skills to ensure underwriting, finance, operations and DAT agree and execute against the approved project list. Demonstrated ability to manage and develop large, distributed teams, including onshore/offshore staffing models. Comfortable driving outcomes and unblocking execution, not just facilitating alignment. PMP, CPCU, or similar professional designation a plus. Our 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 intentionally to deliver on our mission. We value diversity and are committed to creating an inclusive environment for all employees. At Vantage, we strive to build and foster a culture where inclusiveness is ingrained, not just an initiative. All colleagues support building an inclusive environment where employees feel empowered to share their experiences and ideas to foster an environment which encourages you to "Be You!" We are proud to be an equal opportunity employer. In connection with our business, Vantage may collect and process your personal data. For further information

regarding how we use this data, please see our online privacy notice at

Vantage Recruiting Privacy Notice.

ADA Notice: All applications shall be submitted online through our applicant tracking system. Candidates needing reasonable disability accommodation to enable them to apply and/or fully participate in the selection process are encouraged to email

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with the subject Candidate ADA Request detailing their needs. Please note the above email box is for candidates needing reasonable disability accommodation only, emails submitting resumes will not be considered and those seeking application status updates will go unanswered.