Executive Assistant

Brand new office with free daily coffee, on‑site gym and flexible workspace. Enjoy discounts on all Winning Group products plus other retailers. Join a proudly Australian owned, family operated group. 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're a fourth‑generation, family owned business driven by innovation, sustainability, and creating the best experiences for our customers, our people, our communities and the planet. The Opportunity This is not a typical Executive Assistant role, because Winning Group is unlike any other business. We are looking for a rare operator who loves operating close to the action and who is energised by variety, pace and complexity. As an Executive Assistant at Winning Group, you will be the trusted right hand across both business and selected personal domains. On any given day you might be shaping a complex leadership off‑site, preparing an Executive for a strategy meeting, coordinating travel across multiple time zones, and quietly making sure that key life logistics are handled behind the scenes so they can perform at their best. 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; and is comfortable working collaboratively with another support role to create a seamless, well‑coordinated experience. You will work closely with a direct report, the House Manager and PA, who focuses on household and personal logistics. Together, you will create a seamless experience around the Executive, with you leading and coordinating how business and life support come together. We are very clear about balance. There will be moments where you lean in outside standard hours, particularly around travel, key events or urgent issues. In return, we plan ahead wherever possible, respect time off, and work with you to make this sustainable for the long term. What You Will Be Doing Strategic Executive Support Partner with the Executive to ensure their time, attention and energy are focused on the most important work for the Group. Prepare and refine documents, presentations and briefing notes so the Executive arrives prepared and confident. 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 and make smart, commercial decisions about what is in and what is out. Balance Board, Executives, 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 where appropriate. Be a professional first point of contact for the Executive, 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, ensuring household and personal logistics run smoothly. 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, particularly where these intersect or enable business outcomes. Coordinate life logistics around major work commitments, ensuring the Executive can focus fully when it matters most. Be comfortable that your support sometimes extends beyond a standard nine to five, with flexibility and mutual respect around how that is managed. Meetings, Governance and Events Coordinate Executive and Board related meetings, including agendas, papers and logistics. Capture and track actions so that agreements turn into outcomes. Organise and support internal events, customer and supplier visits and external engagements, making sure the Executive is always well briefed. Who You Are Experience At least 5 years experience 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 a 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 for the Executive. 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, for the world. Why You Will Love Working With Us Supportive team culture and a 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 where you start, not where you finish. 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