Billing Specialist & Customer Services Retentions Manager

This is a remote position.

Role Overview

We are seeking a Billing Specialist & Customer Service Retention Manager who will take end-to-end ownership of our billing operations, customer support functions, and client retention strategy.

This is a foundational role, ideal for a self-starter ready to build and co-design the Finance and Customer Support department — including systems, processes, people, and policies — from the ground up. You will play a pivotal role in shaping the operational infrastructure that supports Scoutnet’s growing insurance and financial product portfolios.

• Partner with leadership to build out the Finance & Customer Support department, including staffing, systems selection, and SOP development.
  
• Design scalable workflows for billing, retention, missed collections, and client escalation handling.
  
• Set up foundational reporting, KPIs, and feedback loops to track billing health and customer satisfaction.
  

Billing & Debit Order Management

• Architect and manage end-to-end debit order processes, including collections, retries, reversals, and reporting.
  
• Liaise with debit order service providers and ensure technical and financial alignment.
  
• Administer insurance policy books with accurate reconciliation of premium payments vs. policy status.
  
• Oversee missed debit resolution and develop proactive collection strategies.
  
• Track and escalate premium-related issues to ensure policy integrity and compliance.
  

Customer Service & Retention

• Handle and resolve customer queries related to claims, billing issues, missed payments, and cancellations.
  
• Build and train a customer support team capable of managing inbound and outbound retention workflows.
  
• Implement retention strategies for clients at risk of lapsing, using data-driven engagement and objection handling.
  
• Ensure a seamless claims experience by coordinating with underwriters and policy administrators.
  

Compliance & Process Excellence

• Document all billing, retention, and support processes for internal use and audit compliance.
  
• Ensure strict POPIA compliance in all customer communications and data handling.
  
• Contribute to onboarding new insurance products/books, ensuring systems and service readiness.
  

Requirements

Experience & Skills:

• 3+ years in billing, finance operations, customer service, or insurance administration.
  
• Proven ability to manage and improve debit order collection systems.
  
• Demonstrated experience in building or scaling a support or finance function.
  
• Proficiency in using CRM and ticketing systems (e.g., Salesforce, Zoho, Freshdesk).
  
• Strong analytical, process-mapping, and reconciliation skills.
  
• Excellent communication, leadership, and negotiation skills.
  

Bonus if you have:

• Insurance, claims, or financial services background.
  
• Project management experience.
  
• Experience with tools like Debi Check, Netcash, Sage, or Xero.
  

Benefits

What We Offer

• Competitive market salary + performance incentives.
  
• Flexible working model (remote/hybrid).
  
• High-growth environment with real ownership.
  
• Opportunity to build a department from scratch and make a tangible business impact.
  
• A mission-driven team culture focused on integrity, efficiency, and service.