Associate Director of Rewards

At Winston Taylor, we set the standard, together.

Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up.

You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand.

You’ll be trusted with real responsibility from the outset and build experience through hands-on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations.

Step into the moments that matter. Join Winston Taylor.

The Associate Director of Total Rewards serves as a key member of the Total Rewards leadership team and strategic partner to the Director of Total Rewards in shaping the Firm's compensation, benefits, and wellbeing strategy. This role is responsible for the design, delivery, and continuous improvement of the Firm's compensation, benefits, and wellbeing programs, ensuring they are competitive, compliant, financially sustainable, and aligned with business objectives.

As a trusted advisor to firm leadership, the Associate Director serves as a highly collaborative leader across the Firm's global Talent organization, partnering closely with colleagues in London and other international offices to promote alignment of Total Rewards philosophy while respecting regional market practices, regulatory requirements, and business needs.

Success in this role requires exceptional relationship-building skills, strong leadership, executive presence, and the ability to influence and collaborate effectively across a complex, matrixed professional services environment.

• Architect, evaluate, and continuously improve all global health & welfare benefit programs, ensuring they serve as a lever for talent attraction and retention (including health, dental, vision, life, disability, wellness, leaves, and open enrollment).
• Partner with the Director of Total Rewards to develop and execute a progressive benefits strategy that anticipates future market trends and aligns with the Firm's business priorities and workforce needs.
• Leverage data analytics, benchmarking, and market intelligence to assess program effectiveness, forecast trends, and recommend strategic enhancements.
• Lead relationships with benefit vendors, brokers, consultants, and third-party administrators; drive annual renewals, strategic budget planning, and financial forecasting.
• Drive benefit plan strategies and design recommendations in collaboration with insurance brokers, and present recommendations to the Insurance Committee.
• Serve as a key administrative member of the Insurance Committee, ensuring compliance and structural integrity of all Plan Descriptions, documentation, and communications.
• Ensure compliance with all federal, state, and local regulations (ERISA, ACA, COBRA, HIPAA, FMLA, etc.), staying ahead of regulatory shifts to mitigate firm risk.
• Develop and execute comprehensive communication strategies that increase employee understanding and appreciation of Total Rewards offerings.
• Lead and develop members of the benefits team, fostering a culture of accountability, collaboration and continuous improvement.
• Direct the work of outside consultants and internal teams to ensure successful execution of annual audits and complex regulatory reporting (ACA, Form 5500, FAS 106, Rx Reporting).
• Oversee complex leaves of absence (FMLA, Paid Family Leave, workers' compensation, STD and LTD), ADA accommodations, and escalated benefits matters in partnership with HR Business Partners and legal counsel.
• Lead the strategic execution of annual Open Enrollment, ensuring seamless technology integration, executive-level communication, and an exceptional employee experience.
• Partner closely with EME Talent leaders to promote alignment and consistency across global benefits and wellbeing programs while respecting regional requirements and market practices.
• Build strong relationships with firm leaders and business professionals to understand evolving workforce needs and ensure Total Rewards programs support attraction, engagement, and retention objectives.

• Lead compensation analytics, market trend analysis, and reporting efforts to provide…