Director/Senior Director, Financial Planning & Analysis

Windsor is a fast-growing, fashion-forward omni-channel retailer with a bold, trend-driven brand and a strong national footprint, now entering an exciting next phase of growth focused on scaling intelligently, continuous improvement, and driving performance across every part of the business. Our culture is rooted in doing more with less, going above and beyond, operating with financial discipline, and innovating quickly in a constantly evolving retail landscape.

We are seeking a strategic, forward-thinking Director/Senior Director of FP&A who thrives in this environment—someone equally comfortable setting vision and rolling up their sleeves, highly analytical, curious, energized by solving problems, building processes, and transforming the business. This high-visibility role partners closely with the CFO and leadership team to guide company-wide planning, deliver actionable performance insights, and influence decisions that drive growth, profitability, and shareholder value.

At Windsor, it’s not just about reporting numbers—it’s about owning the narrative behind them. This is an opportunity for a dynamic finance leader who seamlessly connects strategy to execution and is excited to make a meaningful impact on an internationally recognized fashion brand.

Essential Job Functions & Responsibilities:

This role calls for a commercially minded finance leader with strong experience managing multi-market retail operations, ideally within fashion retail or broader consumer-focused environments.

• The Director/ Senior Director, FP&A is a strategic role partnering cross-functionally to drive financial performance, operational efficiency, and long-term value creation
• This role partners with business and operational leadership to provide financial insights, ensure robust planning and forecasting, and support data-driven decision-making
• Leading and managing the entire budget, forecasting, and long-range planning process
• Partner with the CFO on the weekly, monthly, and quarterly basis for reporting, review process and interactions with our Board of Directors
• The Director/Senior Director, FP&A will lead the FP&A functions ensuring accurate financial reporting, budgeting, and performance analysis
• Partner with functional leaders to develop and track KPIs across all business units
• Drive Windsor’s financial strategy, improving cost efficiency, and supporting growth initiatives such as store expansion, entry into new markets, and the advancement of our digital and eCommerce capabilities
• Analyzing financial performance, market trends, and business initiatives to identify opportunities for growth, margin improvement, and operational efficiency
• Developing and executing the finance strategy to align with the company's regional and global objectives
• Driving continuous improvement in FP&A processes, leveraging data analytics to deliver timely and accurate financial insights
• Championing finance transformation initiatives, including implementing AI into analysis, automation of processes and the enhancement of financial systems
• Driving improvements in financial and operational processes to increase efficiency and scalability
• Leading, mentoring, and developing their team, fostering a culture of excellence and accountability
• Leading financial due diligence for potential partnerships

Key Qualifications & Requirements:

• Bachelor’s degree required; MBA preferred.
• 10+ years of progressive FP&A or finance experience, including team leadership.
• Proven success in influencing executive stakeholders and scaling financial processes.
• Advanced Excel and PowerPoint expertise with strong storytelling capabilities.
• Experience in retail or broader consumer-focused environments is highly valued.
• Agility, precision, and the ability to manage complexity in a fast-moving environment.
• A proactive mindset with a bias toward action and results.

Physical/Environmental Demands and Overtime & Availability: Work is performed in an office environment and requires the ability to operate standard office equipment and keyboards. Must have the ability to walk short distances. Sedentary work. Exerting up to 10 pounds of force occasionally and/or a small amount of force frequently or constantly to lift, carry, push, pull or otherwise move objects. Repetitive motion. Adequate movements (motions) of the wrists, hands, and/or fingers. Team members are required to have close visual acuity to perform activities such as: preparing and analyzing data and figures; transcribing; viewing a computer terminal; extensive reading.

*Job descriptions are merely a summary of the position. Duties and responsibilities are subject to change and may include any other that management finds necessary to successfully maintain business operations.

WINDSOR EQUAL OPPORTUNITY EMPLOYEE