Program Director - Employee Benefits Transformation
About the Role
We are seeking an exceptional Program Director to lead a landmark digital transformation of our employee benefits ecosystem. This strategic role requires someone who combines deep expertise in employee benefits operations with proven capability in delivering complex, technology-enabled transformation programs. You'll be architecting and implementing the future of how we support our employees through their benefits journey.
Key Responsibilities
Lead an enterprise-wide transformation of employee benefits platforms, systems, and processes to deliver a seamless, digital-first experience
Develop and execute a comprehensive program strategy that modernizes benefits administration, enrollment, and ongoing employee engagement
Oversee the evaluation, selection, and implementation of benefits technology platforms and integrated solutions
Drive transformation across the full benefits lifecycle including enrollment systems, total rewards platforms, pension administration, healthcare management, and voluntary benefits solutions
Establish robust integration architectures connecting benefits platforms with HR systems, payroll, time and attendance, and other enterprise applications
Lead organizational change to drive adoption of new benefits tools, self-service capabilities, and digital channels
Partner with HR, Compensation & Benefits, IT, Finance, and vendor management teams to ensure aligned delivery
Create governance frameworks for ongoing benefits platform management, vendor relationships, and continuous improvement
Manage complex vendor ecosystems including benefits administrators, technology providers, and consulting partners
Ensure compliance with regulatory requirements and data privacy standards throughout the transformation
Define success metrics and demonstrate measurable improvements in employee experience, operational efficiency, and cost effectiveness
Essential Experience & Skills
Employee Benefits Expertise (Critical):
Extensive hands-on experience with employee benefits administration, operations, and strategy
Deep knowledge of benefits platforms, technologies, and vendor landscape including solutions such as Workday Benefits, SAP SuccessFactors, Oracle HCM Benefits, Mercer, Willis Towers Watson, Aon, or similar
Understanding of benefits types including health and welfare, retirement/pensions, voluntary benefits, flexible benefits, and total rewards statements
Experience with benefits enrollment technologies, decision support tools, and employee communication platforms
Familiarity with benefits data integration, file feeds, eligibility management, and carrier connectivity
Knowledge of benefits compliance requirements, regulatory frameworks, and reporting obligations
Digital Transformation & Program Leadership:
Proven track record delivering complex, multi-year digital transformation programs in large organizations
Experience managing enterprise technology implementations with budgets of £10M+
Strong understanding of system integration patterns, API architectures, and data management
Expertise in evaluating and selecting SaaS platforms and managing vendor implementations
Experience with HR technology ecosystems and integration between benefits, payroll, HRIS, and related systems
Ability to balance custom development with configurable solutions and platform capabilities
Leadership & Delivery:
Exceptional stakeholder management with ability to engage C-suite, HR leadership, and employee populations
Strong program governance skills with experience managing multiple workstreams, dependencies, and risks
Experience leading organizational change management for employee-facing transformations
Ability to translate complex benefits and technical concepts for diverse audiences
Track record of delivering measurable business outcomes and demonstrating ROI
Experience building business cases and securing investment for transformation initiatives
Desirable Experience
Background in the insurance or financial services sector
Property & Casualty (P&C) insurance industry knowledge
Experience with benefits programs in highly regulated industries
Familiarity with pension scheme administration and DC/DB platforms
Knowledge of benefits outsourcing models (BPO) and shared services
Experience with employee wellbeing platforms and total rewards technologies
Understanding of benefits analytics, reporting, and data visualization tools
What We're Looking For
You'll be someone who genuinely understands the employee benefits landscape—not just from a strategic perspective, but with real operational knowledge of how benefits systems work, what makes implementations successful, and where the common pitfalls lie. You'll have lived experience navigating benefits vendor relationships, managing open enrollment transformations, and driving system consolidations or upgrades.
We need a leader who can bridge the worlds of benefits expertise and technology transformation—someone equally comfortable discussing dependent eligibility rules and API integration strategies. You'll bring both the credibility to engage benefits professionals and the technical fluency to drive platform modernization.
Your approach will be pragmatic and employee-centric, always keeping the end user experience at the forefront while managing the complex backend systems and processes that enable it.
Our Offer
This is a rare opportunity to fundamentally reimagine how employees experience and engage with their benefits. You'll lead initiatives that directly impact thousands of employees' lives, making it easier for them to understand, access, and maximize the value of their benefits.
You'll work with cutting-edge benefits technology, shape vendor partnerships, and build capabilities that will serve as the foundation for years to come. This role offers genuine autonomy, strategic influence, and the backing of senior leadership to drive meaningful change.
We offer competitive compensation, comprehensive benefits (naturally), flexible working arrangements, and significant opportunities for career progression within our organization.