Sales Director - South Africa

Sales Director For South Africa

As Pinewood.AI continues to grow its global footprint, we are investing in senior leadership to accelerate our expansion across South Africa and selected African markets. We're looking for an experienced Sales Director to lead this growth, someone who can shape market strategy, open senior-level doors, and build long-term, high-value partnerships across the automotive ecosystem.

This is a senior, high-profile role with full accountability for regional revenue growth. You'll take an insight-led, consultative approach to sales, working with customers to challenge assumptions, diagnose complex operational and commercial challenges, and position Pinewood.AI as a strategic transformation partner. You'll operate confidently at the executive and board level, navigating complex, multi-stakeholder sales cycles while building a sustainable pipeline across OEMs, dealer groups, and commercial operations.

The role will be based in Johannesburg, with regular travel to customer sites across South Africa and selected African markets as required.

Key Responsibilities:

• Own and lead Pinewood.AI's commercial strategy across South Africa, setting clear priorities, revenue targets, and routes to market across the full Pinewood.AI product portfolio.
• Shape and execute a structured go-to-market approach, defining priority segments, target accounts, and expansion opportunities across South Africa and selected African markets.
• Establish Pinewood.AI's presence as a credible, strategic technology partner, with responsibility for supporting market entry and growth under defined, ring-fenced commercial models where appropriate.
• Proactively generate new opportunities through executive networking, referrals, and strategic introductions, rather than reliance on inbound demand.
• Establish and maintain trusted, senior-level relationships with OEMs, NSCs, large dealer groups, and commercial partners across the region.
• Lead discovery-driven, consultative sales engagements that uncover latent needs, shape customer vision, and influence buying criteria before formal procurement processes begin.
• Build, manage, and forecast a balanced sales pipeline, combining near-term opportunities with longer-term, high-value strategic deals to drive consistent revenue growth.
• Navigate and lead complex, multi-stakeholder negotiations, shaping commercial structures and ensuring Pinewood.AI is positioned as the preferred long-term technology partner.
• Own the commercial close, maintaining confidence, momentum, and executive alignment throughout the sales cycle.
• Use market intelligence, customer insight, and performance data to continuously refine regional sales strategy, positioning, and go-to-market execution.
• Work closely with internal teams to align customer engagement strategy, solution positioning, and commercial models to market needs.
• Provide leadership and direction that fosters a high-performance, results-driven, opportunity-focused sales culture, with accountability against performance-based objectives.

Requirements:

• Provide leadership and direction that fosters a high-performance, results-driven, opportunity-focused sales culture, with accountability against performance-based objectives.
• Extensive experience in the Automotive retail industry.
• Strong relationship builder, with an established network in the South African automotive sector.
• Understanding of how dealerships operate and the challenges faced by users in these roles.
• Extensive experience in senior B2B sales leadership roles, with a strong track record of delivering revenue growth through complex, high-value deals.
• Deep understanding of enterprise and consultative sales methodologies, with experience selling insight-led, value-based technology solutions.
• Proven ability to open doors in under-penetrated markets and build credibility with senior decision-makers.
• Comfortable operating at board and C-suite level, presenting strategic recommendations and commercial cases.
• Commercially strategic, able to manage and prioritise opportunities across varied deal sizes and sales cycles.
• Strong negotiation and stakeholder management skills, with experience leading complex, multi-party deals.
• Performance-driven and motivated by targets and incentives.
• Experience operating across multiple African markets or emerging economies, with an understanding of regional business dynamics.
• Familiarity with Pinewood.AI (formerly Pinewood Platform / Pinnacle) or equivalent solutions.
• Based in Johannesburg, with the flexibility to travel across South Africa and other key market locations.

Why Join Us?

At Pinewood.AI, we're building technology that genuinely makes a difference to how automotive retailers and OEMs work. As Sales Director for South Africa, you'll have a real opportunity to shape our presence in the region, influence strategy, build partnerships, and drive growth in a way that leaves a lasting impact.

You'll be joining an ambitious team, backed by a culture that values communication, collaboration, and ownership. We care about solving real problems for customers and about how we work together to do it. From day one, you'll be supported to grow through structured learning, exposure to global teams, and the freedom to bring your ideas to the table.

With proven products, a clear vision for growth, and strong backing from an international business, this is a chance to do meaningful work in a fast-moving technology environment. You'll thrive here if you're curious, solution-focused, and motivated by making things better, not just bigger.

About Us:

Our story began more than 20 years ago, but right from the start, it has been rooted in the specific needs of the automotive industry. As automotive professionals as well as technologists, we wanted to build practical technology solutions that were designed around how automotive businesses work, recognising what makes them different. Pinewood.AI is an unparalleled Automotive Intelligence Platform that enables automotive retail customers and OEMs to drive growth and profitability throughout every aspect of their business.

Pinewood's cloud-based secure end-to-end ecosystem unlocks the value of every customer. Our vision is to be the full-service technology partner that helps automotive retailers and OEMs run more efficiently and increase revenue by making better commercial and business decisions more easily.