Director of Configuration and Analysis (Tampa)

Description

The Director, Configuration & Analysis is responsible for leading a multi-functional U.S. and offshore organization that serves as the enterprise center of excellence for tax-favored employee and retiree benefits spending accounts (HSA, FSA, HRA, ICHRA, etc.). The scope of this role includes configuration, business analysis, data analysis, validation, governance, and platform consulting across WTW's Individual Marketplace business.

The role provides strategic leadership and operational oversight for client implementations, ongoing configuration management, quality assurance, funding and payment support processes, business requirements analysis, and delivery readiness activities. The Director ensures that system configuration aligns with client intent, contractual obligations, regulatory requirements, and operational best practices while developing scalable processes, documentation standards, and colleague capabilities across the organization.

The Director leads the Configuration & Analysis team's transformation toward an any platform, any colleague operating model through cross-training, proficiency development, operational standardization, and continuous improvement initiatives. 

Key Responsibilities

Leadership & Talent Development

• Lead and develop a U.S. and offshore team supporting configuration, analysis, validation, and operational readiness.
• Build organizational capability through workforce planning, cross-training, succession management, and colleague development.

Configuration & Business Governance

• Establish and monitor standards, metrics and controls for configuration, business analysis, validation, issue remediation, and solution delivery.
• Serve as the senior escalation point for complex configuration, platform, and operational design decisions.
• Oversee implementation, configuration, and operational support activities to ensure quality, consistency, and successful client outcomes.
• Partner across Operations, Product, Technology, Compliance, and Client Services domains to deliver scalable solutions and business priorities.

Quality, Risk & Continuous Improvement

• Ensure effective quality assurance, validation, documentation governance, and risk management practices.

• Ensure configuration, validation, and change control practices support regulatory compliance, contractual obligations, audit readiness, and defensible control evidence.

• Lead root cause analysis for configuration-related issues, using methods such as 5 Whys to prevent recurrence and improve standards, training, controls, and procedures.

• Drive automation, standardization, process improvement, and operational resiliency initiatives.

Qualifications

• 10+ years of leadership experience in operations, configuration, business analysis, implementation, or related business functions.
• 5+ years of people leadership experience, including leading multi-location teams and leading teams through large-scale operational, system, or business transformation initiatives.

• Demonstrated experience leading configuration governance, quality controls, validation practices, change control, audit readiness, and issue remediation in a complex operating environment.

• Experience supporting health and welfare benefits administration, health insurance marketplace, Medicare, ICHRA, spending accounts, or related benefits platforms.

• Knowledge of Federal regulatory requirements impacting health and welfare benefits administration, spending account administration, Medicare, ICHRA and consumer-directed health programs, including ERISA, HIPAA, COBRA, IRS Code Section 125, the Affordable Care Act, and related agency guidance.

Required Skills

• Ability to translate complex business requirements into scalable configuration, reporting, and operational solutions.
• Strong proficiency with Microsoft Excel, Power BI, and data analysis tools, including the ability to interpret operational trends, validate data quality, and translate findings into business actions.
• Demonstrated proficiency with Oracle, Microsoft SQL Server, or similar relational database environments.
• Demonstrated experience with Python or similar scripting languages to support data analysis, automation, quality checks, prototyping, and process improvement opportunities. 

• Understanding of APIs, system integrations, business rules, data flows, and platform configuration concepts sufficient to partner effectively with Technology and Product teams.

• Experience using Agile delivery tools and methods, such as Jira, Azure DevOps, user stories, acceptance criteria, sprint planning, backlog prioritization, and release readiness practices.

• Demonstrated experience with AI-enabled productivity and analysis tools, including Microsoft Copilot, ChatGPT, Claude, or similar technologies tools to accelerate analysis, process documentation, test scenario development, root cause analysis, and decision support while maintaining appropriate governance, privacy, and validation standards.

Compensation and Benefits 

Benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation (Producer roles only).

Compensation 

The salary compensation range being offered for this role is $125,000.00 to $135,000.00 USD. 

This role is also eligible for an annual short-term incentive bonus. 

Company Benefits:

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

• Health and Welfare Benefits:  Medical (including prescription coverage), Dental, Vision, Health Savings Account, Commuter Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)
• Leave Benefits: Paid Holidays, Annual Paid Time Off (includes paid state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave),  Paid Time Off
• Retirement Benefits:  Contributory Pension Plan and Savings Plan (401k). All Level 38 and more senior roles may also be eligible for non-qualified Deferred Compensation and Deferred Savings Plans

Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records.

EOE, including disability/vets