VP, Head of Technology Enablement

Vantage Group Holdings Ltd

• $225K — $285K *
Finance & Insurance
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 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.
  • Proven track record leading enterprise-wide portfolios of underwriting and operational transformation initiatives across multiple regions.
  • Experience in establishing project governance and intake frameworks, including executive steering committee facilitation.
  • Deep working knowledge of underwriting and claims administration systems (e.g., Majesco, Guidewire).

Responsibilities

  • Lead a portfolio of underwriting and technology transformation initiatives to drive scalability.
  • Serve as the primary link between underwriting businesses and DA&T, ensuring cohesive project alignment.
  • Establish a structured project governance framework for evaluating and prioritizing new initiatives.
  • Spearhead executive steering committee reviews for strategic project decisions.
  • Partner with leadership to develop a technology enablement roadmap for business growth.

Benefits

  • Performance-based bonus potential
  • Strong health and welfare benefits
  • Comprehensive retirement plans
  • Competitive time-off plans
  • Highly flexible work environment
Full Job Description
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to partner with DA&T to evaluate, prioritize and continually evolve best-in-class systems rather than work around outdated ones.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.

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