New York - Associate Director of Total Rewards

About us

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.

Position summary

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.

Position Responsibilities

Benefits & Wellness

• 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.

Compensation

• Lead compensation analytics, market trend analysis, and reporting efforts to provide leadership with data-driven insights to shape business professional compensation architectures.
• Own the communication strategy for all compensation-related matters, ensuring transparency, equity, and alignment with firm culture.
• Oversee the firm's business professional and paralegal compensation structures, including annual merit, promotional, and market adjustment processes.
• Govern market-pricing strategy and framework for new and existing positions to ensure internal equity and external competitiveness.
• Monitor compensation trends, pay transparency requirements, and emerging market developments to provide strategic recommendations to firm leadership.
• Ensure compensation-related processes, systems and classifications remain compliant with applicable wage and hour regulations.
• Collaborate with Talent, Finance, and business leaders across regions to ensure compensation programs support firm strategy, talent objectives, and a consistent employee experience globally.
• Partner with recruiting leadership to assess market competitiveness and ensure compensation strategies support the firm's talent acquisition and retention goals.

Total Rewards Strategy and Leadership

• Drive the evolution of a holistic total rewards philosophy that seamlessly integrates compensation, benefits, wellbeing, and employee experience to enhance organizational performance.
• Serve as a strategic thought partner to firm leadership on workforce trends, employee value proposition, and Total Rewards strategies that support organizational growth and business performance.
• Collaborate closely with global Talent leaders, including EME colleagues, to identify opportunities for greater consistency, efficiency, and scalability across Total Rewards programs.
• Lead cross-functional strategic initiatives, involving HR technology process optimization automation and employee experience enhancements.
• Design and implement wellbeing initiatives that strengthen employee engagement and support wellness initiatives (physical, mental, and financial).
• Lead through influence across a matrixed environment, building strong partnerships with HR, Finance, IT, Recruiting, and business leadership.

Experience, skills, and qualifications

• Bachelor's Degree required; Advanced degree or professional certification ( CEBS, CCP, or SPHR or equivalent) preferred.
• 10+ years of progressive experience leading Total Rewards, Benefits, Compensation, or related HR functions within a complex, professional services organization required.
• Must live within a commutable distance to a local office and be willing to come into the office 3-4 days per week.
• Demonstrated experience designing and administering comprehensive compensation and benefits programs.
• Executive-level written and verbal communication skills, with a proven ability to influence senior stakeholders.
• Advanced analytical capability, with the ability to translate complex data into strategic business recommendations.
• Deep expertise in global benefits regulations, compensation compliance, and evolving industry best practices.
• Client-service orientation with a track record of resolving highly complex organizational challenges with innovative solutions.
• Ability to build credibility and influence senior leaders, exercising sound judgment in complex and sensitive situations. Proven ability to lead, coach, and develop high-performing teams while fostering a collaborative, and inclusive culture.
• Exceptional interpersonal skills with a demonstrated ability to establish trusted partnerships across all levels of the organization.
• Ability to lead through ambiguity, drive organizational change, and gain buy-in for new programs, processes, and strategies
• Ability to connect Total Rewards strategies to business objectives and deliver solutions that support firm performance.
• Demonstrated ability to manage highly confidential information with discretion, professionalism, and sound judgment.

BENEFITS

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.

SALARY

New York applicants only: The target annual salary range for this role is currently $185,000-$235,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences. #LI-DC2 #LI-HYBRID