Listing reference: cartr_000783 Listing status: Online Apply by: 30 June 2026 Position summary Industry: Distribution, Transport & Logistics Job category: Others: Transport and Logistics Location: George, Western Cape Contract: Permanent EE position: No Introduction Picup, a last-mile delivery and technology-focused company, powered by a scalable crowd-sourced driver network, seeks a highly organised Infield Supervisor with excellent communication skills to be responsible for driver performance, driver branding, driver supply and client satisfaction relating to our delivery as a service. This role entails building trust and loyalty with one of our biggest clients, the store staff and its managers, thereby contributing to the success and growth of our delivery network. Job description The Driver Supervisor is responsible for driver performance, driver branding, driver supply and client satisfaction relating to our delivery as a service. This role is pivotal in building trust and loyalty with one of our biggest clients. Key Responsibilities: Driver Performance: Oversee driver performance metrics and identify opportunities for improvement. Collaborate with underperforming Independent Contractors to craft action plans for improvement, while duly recognising and rewarding top-performing drivers. Driver Branding: Ensuring that Picup Plus Legends meet minimum branding requirements on a daily basis while in a booked slot for Picup while also assisting with distribution of gear where required. Compliance: Guarantee that drivers meet all quality prerequisites, conducting periodic assessments of drivers in the field and escalating where compliance is not met. Reporting: Generate regular reports on Independent Contractor performance and KPIs. Utilise data-driven insights to propose enhancements for Independent Contractor performance and ratings. Driver Supply: Daily driver attendance reporting and tracking to ensure SLA is met and coverage is maintained. Relationship Building: Build strong relationships with the Plus Legend network as well as client Store Managers and Supervisors to promote a positive working environment between both parties. Effectively collate field reports on existing store processes and adherence thereof. Store Launches: Working closely with the Picup Ops, Driver Recruitment and Driver Supervisor teams, assisting on-site with the rollout of any new store launches in new or existing areas. Minimum requirements Matric (Grade 12) 2 years’ experience in logistics, operations, or delivery management (preferably last-mile). Own Vehicle (Car) Vehicle must be roadworthy and carry the necessary insurances (Comprehensive cover, Third Party Liability) Exhibits strong interpersonal, leadership and communication skills. Proficiency in problem-solving and conflict resolution. A customer-centric approach with a profound comprehension of driver requirements. Familiarity with the gig economy or on-demand service platforms and KPIs. Proficiency in utilizing communication tools and Google Suite. Capability to work both independently and collaboratively within a team. Able to use and manipulate data in MS Excel/Google sheets in order to make data-driven decisions. Flexibility to work occasionally during evenings or weekends to accommodate driver schedules or client demands.