Hybrid Sales Director

at Pinewood.AI

• Job title: Sales Director
• Job type: Full Time
• Experience level: Lead
• Salary: Not specified
• Degree requirement: No Education Requirement
• Location requirements: Hybrid, Johannesburg, South Africa

About the role

• Sales Director responsible for market strategy and revenue growth in South Africa for Pinewood.AI. Leading consultative sales processes and establishing key partnerships in the automotive sector.

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

• 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.