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?

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.