Digital (Inside) Sales Leader

2 days ago

Milnerton, Western Cape, South Africa SYSPRO Full time

Department:
Direct Sales

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

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