Media Strategy & Solutions Specialist (Cape Town, Johannesburg)

Job description

You’ve defended the media proposal. Now help build—and sell—the product behind a better one.
Pikaboo is developing tools to help media teams turn a brief, inventory and evidence into a defensible recommendation. We’re hiring someone who knows this work firsthand, can sell the product’s value to media teams and can help make it better.
You understand the pressure of a live brief: the inventory needs to fit, the reasoning needs to hold up, and the buyer needs a clear next step. You can spot where a proposal loses credibility and where a workflow wastes time.

What you will own:

• Discover the live proposal or renewal problem, current workaround, deadline, working users and accountable buyer.
• Explain and demonstrate Pikaboo to media-owner sales and strategy teams. Handle commercial and adoption objections and progress suitable opportunities toward a scoped, paid next step with the hiring managers.
• Turn briefs into useful product tests covering audience, geography, inventory, constraints, rationale and evidence.
• Tell us what is useful, what is wrong and what needs to change. Identify what users still rebuild outside Pikaboo, prioritize the first useful fix and test it.
• Devise original AI-assisted workflows, examples and onboarding guidance that reduce manual work while checking commercial facts and evidence.
• Track useful outputs, buyer review, commercial progression and repeat work—not just interest in a demo.

The experience that fits:

• A media proposal or renewal you personally built and defended, including the buyer’s objection and what happened next.
• Media-owner sales strategy, solutions, account management or closely related planning experience. OOH is particularly relevant to the first workflow; transferable radio or retail-media experience is welcome.
• Understanding of the inventory seller, agency or brand reviewer, and the person who would pay for software supporting the work.
• An AI-assisted improvement you devised: what changed, how you checked it and where it failed.
• Clear, candid communication and the initiative to solve an ambiguous problem, then share a reusable solution.

We value contribution and judgment over employer prestige. You do not need to bring a client list. You do need to explain a buyer’s problem clearly and earn a credible next step.

Why this role:

• Work across the product and commercial process, helping determine what Pikaboo should do and whether media teams value it enough to use and pay for it. Expect hands-on work, fast feedback and assumptions that need testing.

Employment and location:

• Full-time employment; contract arrangements considered. Regular 9–5 hours. Hybrid work from Cape Town or Johannesburg; our offices are in Cape Town. Candidates based in Côte d’Ivoire are also welcome, with the working arrangement discussed during hiring. Compensation will be discussed during the hiring process.

Application and selection:

• Apply through the linked LinkedIn listing with your profile or CV. No cover letter or application video. Be ready to discuss two short examples: a proposal or commercial decision you advanced, and a bottleneck you solved using AI.

Shortlisted candidates meet Phelelani Mkhize and Takalani Malivha for a structured discussion and a 35-minute supplied product case. Explain its value to a buyer, handle an objection and identify what you would preserve, fix and test. No take-home preparation is required. Specific criticism is welcome. No live rate cards, customer lists, confidential employer files, purchase or introduction is required. Any separate research use of feedback will be explained and optional.

Requirements