Executive Assistant

About Us Welcome to Winning Group, where we go beyond the ordinary to create award‑winning retail experiences. As a fourth‑generation, family‑owned Australian business, we combine innovation, technology and luxury in everything we do. We are driven by sustainability and a commitment to delivering the best experiences for our customers, people, communities and the planet. The Opportunity This is not a typical Executive Assistant role. Winning Group is unlike any other business, and we are looking for a rare operator who likes operating close to the action, loves variety, pace and complexity. As an Executive Assistant, you will be the right hand across both business and selected personal domains, shaping complex leadership offsites, preparing the Executive for strategy meetings, coordinating travel across multiple time zones, and ensuring key life logistics are handled behind the scenes. This Role Will Suit Someone Who Thrives in a demanding, high‑trust environment. Is happy to flex their support across work and life where needed. Values being deeply relied upon, not just for diary management but for judgement, discretion and follow‑through. Is comfortable working collaboratively with another support role to create a seamless, well‑coordinated experience. What You Will Be Doing Strategic Executive Support Partner with the Executive to focus their time on the most important work. Prepare and refine documents, presentations and briefing notes. Help manage the flow of priorities, decisions and actions between the Executive and the broader business. Complex Diary and Priority Management Own the Executive’s calendar end to end, making smart commercial decisions about what is in and what is out. Balance board, executive, customer, partner and internal commitments with thinking time and personal commitments. Anticipate pressure points and propose options before they become problems. Communication and Stakeholder Liaison Manage the Executive’s inbox and communication flow, including drafting and editing responses. Be a professional first point of contact, building trusted relationships with senior leaders, board members, partners and key suppliers. Handle highly confidential and sensitive information with absolute discretion. Leadership of House Manager and PA Provide clear direction and priorities to the House Manager and PA. Coordinate how professional and personal support fit together so the Executive has a coherent, well‑managed support structure. Set expectations, standards and ways of working that reflect Winning Group values. Blended Professional and Personal Support Support the Executive across key business activities, travel and selected personal commitments. Coordinate life logistics around major work commitments. Be comfortable with support that sometimes extends beyond a standard nine to five, with flexibility and mutual respect. Meetings, Governance and Events Coordinate Executive and Board related meetings, including agendas, papers and logistics. Capture and track actions so agreements turn into outcomes. Organise and support internal events, customer and supplier visits and external engagements. Who You Are Experience At least 5 years as an Executive Assistant to a senior executive or C‑level leader in a complex, fast‑paced environment. Exposure to retail, eCommerce, logistics or high‑growth, customer‑obsessed organisations is an advantage. Experience handling a blend of executive and personal support for a senior leader is highly regarded. Previous experience leading or mentoring another support role is desirable. Skills and Capabilities Exceptional diary and time management, with talent for making good trade‑offs. Outstanding written and verbal communication skills and a sharp eye for detail. Strong judgement about what needs the Executive, what can be resolved by you and what should be delegated. High level comfort with technology, including Microsoft 365 and collaboration tools. Strong organisational skills and the ability to keep many moving parts under control. Personal Attributes Highly discreet, trustworthy and respectful of confidentiality. Adaptable and resourceful, comfortable when plans change and priorities move. Comfortable with a role that blends traditional EA responsibilities with thoughtful personal support. Calm under pressure, resilient and reliable when things get busy. Warm, people‑centred and aligned to Winning Group’s focus on creating the best experiences in the world. Why You Will Love Working With Us Supportive team culture and healthy work‑life balance, even in a high‑trust, high‑responsibility role. Enjoy discounts on all Winning Group products, plus access to partner retailer offers. A strong focus on promoting from within so you can grow with us. The chance to work directly with an entrepreneurial senior leader and executive team in a fourth‑generation Australian family business. Real impact and visibility of your work will shape how the Executive shows up for the business every day. #J-18808-Ljbffr