Digital; Inside Sales Leader

Digital (Inside) Sales Leader – SYSPRO

Location: Milnerton, Western Cape, South Africa

Department: Direct Sales

We are seeking a dynamic and energetic Digital Sales Leader to manage our Digital Sales Team, which includes both new business and existing account managers. In this strategic role, you will be responsible for driving a sustainable, high‑quality pipeline, delivering world‑class sales execution, and developing a team of future sales rockstars.

• Consistently deliver against revenue targets with predictable performance.
• Grow ARR through cross‑sell, upsell and activation of SYSPRO’s expanding product portfolio (Finance, Manufacturing, Supply Chain).
• Position the SYSPRO brand and solutions within the mid‑market manufacturing and distribution space.
• Drive adoption of AI‑powered use cases across the customer base.
• Participate in and reinforce our GTM engine focused on simplifying, standardizing, and automating sales execution (PACE).
• Support long‑term customer migrations to SYSPRO Cloud.

• Lead the Inside Sales Team to achieve ARR, net retention and cross‑sell/upsell targets.
• Develop and execute a repeatable, scalable inside‑sales motion in collaboration with GTM.
• Build pipeline health, forecast accuracy, and thorough deal inspection.
• Recruit, train and coach account executives; champion culture & values.
• Collaborate with marketing on demand generation, events, digital campaigns and lead follow‑up workflows.
• Work with product and customer success to validate use cases, provide feedback, and support AI adoption.
• Own forecast accuracy, pipeline reporting, KPIs, territory analytics and continuous process improvement.

• Minimum 4 years in a sales leadership role, ideally managing early‑career or developing sales talent within a high‑performing digital sales environment.
• Proven track record of consistently meeting or exceeding quarterly and annual sales targets.
• Strong ability to lead, coach and inspire a sales team to achieve and exceed goals.
• Familiarity with ERP solutions or other complex business applications is highly desirable.
• Experience developing a digital sales team in multiple locations and geographies.

Mid‑Senior level

Full‑time