Winners Executive and Leadership Team

September, 2026

Leadership Overview

Winners has 4 executives leading key functions including strategy, organizational development, financial oversight, and operational management.

Focused on delivering exceptional value to Canadian consumers, Winners maintains a commitment to providing high-quality brand-name merchandise at competitive prices while fostering a culture of continuous retail innovation.

Leadership Roles at Winners

  • Chief Executive Officer & Educational Speaker - Keith Davis
  • Founder & Chief Executive Officer - Helder Roger
  • Chief Financial Officer - Jim Patient
  • President - Jose Garcia- Pineyro
  • Keith Davis - Chief Executive Officer & Educational Speaker

    Keith Davis, the Chief Executive Officer & Educational Speaker at Winners, directs the overarching strategic vision for the off-price retail model. By analyzing market trends across the Canadian landscape, Davis architects long-term growth initiatives that align with the broader objectives of the parent organization. The Chief Executive Officer & Educational Speaker also facilitates internal training programs, ensuring that leadership teams understand the nuances of value-based retail. Keith Davis maintains a focus on operational excellence, driving efficiency within the supply chain to ensure consistent inventory availability. Through public engagement and industry speaking, Davis promotes the brand identity to a wider audience. This leadership role requires constant collaboration with the board to refine the competitive positioning of the department store chain. By prioritizing customer satisfaction and cost-effective procurement, Davis secures the market standing of the company within the highly competitive North American retail sector.

    Helder Roger - Founder & Chief Executive Officer

    Helder Roger, the Founder & Chief Executive Officer at Winners, oversees the foundational principles and high-level corporate governance of the retail chain. Roger drives the expansion of the store footprint across Canada, ensuring that the brand reaches diverse consumer demographics. As the Founder & Chief Executive Officer, Roger manages the integration of new product categories, including fine jewelry and home goods, into the existing inventory mix. This executive role involves setting the tone for corporate culture and maintaining the integrity of the off-price business model. Helder Roger monitors the performance of regional operations to ensure that each location meets strict profitability benchmarks. By fostering relationships with global suppliers, Roger secures exclusive deals that define the unique value proposition of the stores. The leadership of Roger ensures that the company remains agile in responding to shifting economic conditions while maintaining a strong presence in the national retail market.

    Jim Patient - Chief Financial Officer

    Jim Patient, the Chief Financial Officer at Winners, manages the fiscal health and capital allocation strategies for the entire retail network. Patient oversees the budgeting process, financial reporting, and risk management protocols that support the company's growth objectives. As the Chief Financial Officer, Patient analyzes revenue streams from various departments, including beauty products and housewares, to optimize profit margins. This role involves coordinating with the executive team to ensure that capital investments in store infrastructure yield high returns. Jim Patient directs the financial planning for regional operations, ensuring that the company maintains a robust balance sheet despite market volatility. By implementing advanced accounting systems, Patient enhances the transparency and accuracy of financial data. The leadership of Patient supports the long-term sustainability of the business by maintaining strict control over operational expenditures and ensuring that the company remains well-positioned for future investment opportunities.
    Jim Patient

    Jose Garcia- Pineyro - President

    Jose Garcia- Pineyro, the President at Winners, executes the day-to-day operational strategies that drive the success of the department store chain. Garcia- Pineyro oversees the logistics and distribution networks that supply stores with brand-name clothing and footwear. As the President, Garcia- Pineyro manages the performance of store managers and regional directors to ensure consistent service standards across the country. This leadership role involves streamlining the customer experience, from inventory display to point-of-sale efficiency. Jose Garcia- Pineyro coordinates with the marketing and merchandising teams to align promotional activities with seasonal demand. By focusing on operational scalability, Garcia- Pineyro ensures that the company can effectively manage the complexities of a large-scale retail environment. The strategic oversight provided by the President directly impacts the ability of the company to maintain its competitive edge in the Canadian market while delivering consistent value to the consumer base.

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    Frequently Asked Questions Regarding Winners Top Executives and Leadership Team

    Who leads Winners?
    Winners is led by Keith Davis (Chief Executive Officer & Educational Speaker), along with executives such as Helder Roger (Founder & Chief Executive Officer) and Jim Patient (Chief Financial Officer).
    Who is part of Winners’s executive team?
    The executive team of Winners includes leaders such as Keith Davis (Chief Executive Officer & Educational Speaker), Helder Roger (Founder & Chief Executive Officer), Jim Patient (Chief Financial Officer) and other senior executives.
    How many executives does Winners have?
    Winners has 4 executives leading key business areas.
    What roles are included in Winners’s leadership team?
    The leadership team of Winners includes roles such as Chief Executive Officer & Educational Speaker, Founder & Chief Executive Officer, Chief Financial Officer, President.