Digital (Inside) Sales Leader

SYSPRO Proprietary Limited; Cape Town; On-site; ZAR 500 000 - 700 000; Full time

Job summary

A leading technology company is seeking a Digital Sales Leader to manage their dynamic Digital Sales Team in Cape Town. The role involves driving revenue execution and achieving sales targets while coaching and developing early-career sales talent in a high-performing digital sales environment. Candidates should have a minimum of 4 years in sales leadership and an understanding of ERP solutions is a plus. This full-time position is located at the company's headquarters in Cape Town.

Qualifications

• 4+ years in a sales leadership role with a digital sales team.
• Track record of meeting or exceeding sales targets.
• Experience with ERP solutions is desirable.

Responsibilities

• Achieve ARR and retention targets across the Inside Sales Team.
• Implement and manage consistent sales processes.
• Ensure forecast accuracy and pipeline health.
• Recruit, train, and coach Inside Sales Executives.
• Drive a culture of growth and customer-centricity.

Skills

Sales leadership

Revenue execution

Sales strategy

Coaching

Customer relationship management

ERP knowledge

Job description

Digital (Inside) Sales Leader

Department: Direct Sales

Employment Type: Full Time

Location: SA | Central | Cape Town

Description

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.

The Digital Sales Leader leads and develops SYSPRO’s growing team of Inside Sales Account Executives, responsible for selling, building customer relationships, and driving revenue within defined territories across new and existing business. This leader will oversee execution of a repeatable, scalable inside sales motion centered on:

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

Key Responsibilities

• Sales & Revenue Leadership
• Revenue Execution: Achieve ARR, net retention, and cross‑sell upsell targets across the Inside Sales Team
• Sales Strategy & Execution: Implement and manage consistent sales processes aligned to the SYSPRO GTM Engine and Sales Execution playbooks
• Pipeline Management: Ensure rigorous forecast accuracy, pipeline health, and deal inspection
• Team leadership and coaching
• Recruit, train, and coach Inside Sales Account Executives
• Champion the SYSPRO values and drive a culture of growth, resilience, and customer‑centricity
• Ensure Inside Sales Executives actively build, deepen, and maintain customer relationships with assigned territories
• Support AI adoption, product positioning, and subscription roadmap discussions
• Go‑to‑market & Cross‑functional alignment – Partner with marketing on demand generation, events, digital campaigns, and lead follow‑up workflows
• Support product and customer success teams with customer intelligence, use case validation, and feedback loops
• Process Improvements: Own forecast accuracy, pipeline reporting, KPIs, and territory health analytics

Skills, Knowledge and Expertise

Required Skills & Qualifications

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