The Lead Associate, Paid Leave plays a critical role in transforming how Protective’s Employee Benefits Business Line delivers and scales Paid Leave programs across all states and markets. This highly visible role will drive modernization of both internal workflows and external experiences, working with a digital‑first, automation‑focused mindset.
This position will also own the lead the build‑out Increased DBL (iDBL) capabilities, ensuring the design, operationalization, and rollout of the new benefit program. In addition, this role serves as an advisor directly to the SVP, Employee Benefits, helping coordinate strategic initiatives, prepare executive deliverables, drive cross‑functional alignment, and ensure operational readiness across the Paid Leave portfolio.
This is a hybrid role blending hands‑on execution, program leadership, operational redesign, and executive support deal for a high‑potential leader with deep understanding of Paid Leave and strong strategic instincts.
Key Responsibilities
Paid Leave Modernization Leadership
Lead end‑to‑end modernization of Paid Leave processes, leveraging automation, digital tools, and workflow redesign.
Partner with Operations, Claims, Underwriting, Distribution, Finance, and Digital Solutions to eliminate legacy bottlenecks and reduce manual work.
Identify and implement process improvements that align with enterprise direction for scalable paid leave expansion.
Support readiness for new state Paid Leave launches by developing future‑state workflows, requirements, and operational playbooks.
Integration of Paid Leave to Enterprise Platform
Lead integration of Paid Leave into the new enterprise benefits platform, ensuring support for multi‑state PFML, DBL, PFL, iDBL, and future statutory programs.
Partner with Product, Operations, Claims, IT, Shared Services, and Digital Solutions to define future‑state platform capabilities, business rules, workflows, automation, and servicing requirements.
Balance dual‑platform operations by maintaining stability, compliance, and customer experience on legacy systems while guiding the design and buildout of scalable new‑platform functionality.
Develop and manage a structured integration plan that enables legacy systems to exchange data with the new platform during the multi‑year transition period.
Ensure brokers, employers, and internal teams experience consistent servicing, reporting, and communications, regardless of whether a customer resides on legacy or new technology.
Create and maintain a phased migration roadmap, establishing criteria, timing, and sequencing for transitioning all legacy Paid Leave customers onto the new platform.
Identify and mitigate operational, regulatory, and technical risks tied to platform transition and modernization activities.
Coordinate cross‑functional change management, including training, readiness plans, SOP updates, and communication rollouts supporting new platform adoption.
Ensure both legacy and new‑platform workflows remain compliant with evolving state regulations, and incorporate new rules into future‑state platform requirements.
Define measurable KPIs for integration success, migration progress, automation gains, and customer experience improvements.
Build & Own iDBL Program
Lead business requirements, state compliance alignment, and operational workflows for increased DBL (iDBL).
Partner with Platform Delivery to define digital intake, automation rules, file exchanges, and servicing requirements.
Conduct gap analysis between current DBL/PFL capabilities and target future‑state iDBL platform.
Coordinate testing, implementation timelines, pilot releases, and stakeholder communications.
Ensure the iDBL solution aligns with scalable operational principles (automation, BPO flexibility, and technology improvement).
Digital‑First & Automation‑Forward Execution
Map current vs. future workflows and partner with Digital Solutions and data teams to embed digital submission, API connectivity, file automation, and self‑service capabilities.
Collaborate with Shared Services and IT teams on modernization dependencies and feasibility.
Identify opportunities for straight‑through processing, document automation, and exception‑based case routing.
Program & Change Management
Lead or contribute to project planning, timeline development, issue logs, and cross‑functional coordination for Paid Leave modernization.
Identify change impacts and support internal training plans, readiness assessments, and deployment.
Maintain detailed documentation of policies, procedures, and process flows.
Market & Regulatory Awareness
Monitor Paid Leave regulatory developments and translate them into operational requirements.
Ensure processes, documents, communications, and workflows remain compliant across states.
Partner with Product, Legal, Actuarial, and Claims to operationalize new rules.
Qualifications
Required
12+ years of experience in Employee Benefits, Paid Leave, Statutory Disability (DBL/PFL), or related insurance operations.
Demonstrated experience in process modernization, automation, or digital transformation.
Strong analytical, strategic thinking, and problem‑solving skills.
Excellent communication and meeting‑facilitation skills.
Proven ability to lead cross‑functional initiatives without direct authority.
Strong technical fluency (workflows, automation, systems, data requirements).
Preferred
Experience supporting state expansion of Paid Leave or statutory disability programs.
Familiarity with DBL/PFL regulations and operational models.
Experience partnering with product, IT, project management, and compliance teams.
Prior exposure to large‑scale organizational transformation.
Success in This Role Looks Like
Paid Leave processes materially simplified, automated, and digitized—with measurable reductions in cycle times and manual work.
iDBL launched on time with clear workflows, governed processes, and strong cross‑functional adoption.
Executive‑ready reporting, roadmaps, and deliverables consistently available for leadership forums.
Cross‑functional teams aligned around Paid Leave modernization roadmap.
SVP Employee Benefits fully supported and operating with greater bandwidth and strategic clarity.
EB viewed as a national leader in Paid Leave operational scalability and customer experience.
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