Group Operations & Commercial Lead – Media & Retail

Group Operations & Commercial Lead – Media & Retail Reporting to: Founder & CEO Location: Cape Town / Hybrid (must be willing to travel to Johannesburg and key operating locations) Employment Type: Full‑time, long‑term growth role Step Into Legacy, what if your next role wasnt just another title but a path to ownership ? Your mission Lead. Integrate. Scale. Youll align operations across three entrepreneurial companies in the digital out-of-home (DOOH), retail media, and subscription-based adtech space ultimately preparing to step into co-ownership or leadership succession over five years. Role Overview Operational alignment and strategic execution across multiple companies. End‑to‑end management support, from business planning to deal negotiation. Acting as a senior representative with clients, partners, property owners, and technical teams. Supporting sales, commercial negotiations, and business development. Leading key initiatives that enhance revenue, profitability, and operational excellence. Mentoring and upskilling team members to uplift performance. This role is both strategic and hands‑on and will require comfort with ambiguity, ability to execute in a fast‑changing environment, and commitment to long‑term business ownership progression. Key Responsibilities Business Leadership & Operations Partner with the Founder to define and drive strategic priorities across all companies. Oversee multi‑disciplinary functions including commercial negotiations, client relations, project management and strategic partnerships. Lead planning, execution and monitoring of high‑impact initiatives and deals. Ensure operational excellence, financial discipline and growth metrics are met. Commercial & Client Engagement Act as primary liaison with external stakeholders, property owners, advertisers, engineers, agents, and corporate clients. Negotiate commercial contracts and major deals aligned with company goals. Support pricing strategy, revenue forecasts and new revenue stream development. Team Leadership & Culture Mentor and coordinate core team members to deliver performance and results. Foster a professional, accountable, and entrepreneurial culture across the businesses. Drive collaborative implementation of modern tools, systems, and communication mechanisms. Strategic Growth & Ownership Progression Help identify new market opportunities and business models. Contribute to long‑term planning for ownership transition and or legacy succession. Lead with integrity, adaptability, and commercial rigor. Ideal Candidate Profile Skills & Experience Business acumen: You think commercially and can translate strategy into measurable results. Communication: Articulate, persuasive, and professional in all business environments. Negotiation: Confident in negotiating deals and commercial contracts. Industry insight: Strong familiarity with media, advertising, retail infrastructure and client‑facing roles (or the ability to learn quickly). Leadership: Capable of driving teams, managing stakeholders, and aligning operations across companies. Adaptability: Comfortable wearing multiple hats, solving complex problems, and operating with agility. Personal Traits Energetic, committed and prepared to invest personally in long‑term business growth. Comfortable representing leadership externally and internally. Entrepreneurial mindset with initiative and self‑drive. Integrity, resilience, and response‑ability. Qualifications Bachelors degree in Business, Marketing, Media, Commerce, or equivalent (preferred). Proven experience in business operations, sales leadership, consulting, strategy, or media. Experience in digital media, advertising, or retail ecosystems an advantage.