Multiskilled On-the-Road Investigator

Pineapple; Johannesburg; On-site; ZAR 420,000 - 680,000; Full time

Job summary

Pineapple is seeking a talented Multiskilled Investigator to join our team in Johannesburg.

The role focuses on protecting the integrity of the claims process by conducting thorough investigations across motor, content and all-risk claims, using fieldwork, desktop analysis, and digital tools. You will collaborate with internal teams and external partners to uncover facts and support fair outcomes.

Qualifications

• Must have a Diploma or relevant qualification in Forensics, Insurance, Law, Risk Management, or related field.
• Experience in the Insurance sector is essential.
• 5-7 years in motor claims investigation, fraud detection or forensic analysis is required.

Responsibilities

• Conduct in-depth investigations into suspected or complex claims across motor, content, and all-risk portfolios.
• Gather and analyse evidence including photos, reports, interviews, receipts, and digital records to validate claim details.
• Identify fraud indicators and escalate cases for further review or legal action.
• Perform site visits, inspections, and desktop investigations using digital tools and third-party data sources.
• Prepare comprehensive investigation reports with findings and recommendations.

Skills

Analytical thinking

Investigative instincts

Stakeholder engagement

Regulatory knowledge (FAIS/POPIA)

Ability to interpret forensic reports

Education

Diploma or relevant qualification in Forensics/Insurance/Law

5-7 years of motor claims investigation experience

Tools

Investigation software

Case management systems

Digital evidence analysis tools

Job description

Pineapple has exciting news to share. We are looking for a talented, passionate and solutions-oriented Multiskilled (OTR) Investigator to join our team.

Pineapple Tech PTY LTD is a dynamic and innovative short-term insurance company that leverages technology to provide exceptional insurance solutions to our customers. We believe in making insurance simple, transparent, and accessible to all. As we continue to grow, we are currently seeking a Multiskilled Investigator to join our dynamic and growing team.

The Multiskilled Investigator at Pineapple plays a critical role in protecting the integrity of the claims process by conducting thorough investigations across multiple domains, including motor, content, and all risk claims. This role ensures that claims are validated accurately, fairly, and in alignment with company policies, underwriting guidelines, and regulatory standards.

Operating within a tech-enabled insurance environment, the Multiskilled Investigator uses a combination of fieldwork, desktop analysis, digital tools, and stakeholder interviews to uncover facts, detect fraud, and support fair outcomes. The role demands strong analytical skills, investigative instincts, and the ability to adapt across diverse case types and technologies.

General Responsibilities, Duties and Undertakings of a Multiskilled Investigator include but are not limited to:

Claims Investigation: Conduct in-depth investigations into suspicious or complex claims across motor, content, and all-risk portfolios. Gather and analyse evidence including photos, reports, interviews, receipts, and digital records to validate claim details against policy terms.

Fraud Detection & Risk Mitigation: Identify potential fraud indicators and elevate cases for further review or legal action. Collaborate with internal fraud teams and external partners (e.g., law enforcement, forensic experts) while maintaining detailed case files and contributing to fraud prevention strategies.

Field & Desktop Assessments: Perform site visits, inspections, and interviews when required, alongside conducting desktop investigations using digital tools, claims platforms, and third-party data sources. Reconstruct incident scenarios and validate item damage or loss consistency.

Reporting & Documentation: Prepare comprehensive investigation reports with findings, conclusions, and recommendations. Ensure documentation is clear, objective, and compliant with regulatory and legal standards before presenting findings to claims teams, legal departments, and senior management.

Stakeholder Engagement: Liaise with claims handlers, assessors, legal teams, and external service providers. Provide guidance and training to internal teams on fraud awareness and support dispute resolution and litigation processes with technical evidence.

Compliance & Ethics: Ensure all investigations comply with data protection laws (e.g. POPIA), industry regulations, and internal policies. Uphold ethical standards, maintain confidentiality throughout the investigation process, and support audit and governance activities.

Required Education and Experience:

• Diploma and or relevant qualification in Forensics, Insurance, Law, Risk Management, or related field
• Experience working in the Insurance sector.
• 5-7 years of experience specifically in motor claims investigation, fraud detection, or forensic analysis

Preferred Education and Experience:

• RE5 (Regulatory Examination), COB and FAIS-related credits strongly preferred.
• Experience in insurtech, digital claims environments, or regulated financial services is highly advantageous
• Certification in fraud examination or forensic investigation is a plus

Required Skills and Competencies:

Technical Competencies

• Strong understanding of insurance claims processes across motor, content, and all-risk portfolios
• Familiarity with fraud detection tools, digital evidence analysis, and item valuation methods
• Proficiency in investigation software, case management systems, and reporting tools
• Knowledge of regulatory frameworks, including FAIS, POPIA, and TCF principles
• Ability to interpret forensic reports, item inventories, and policy documentation

Generic Competencies

• Analytical and detail-oriented with strong investigative instincts
• Objective and fair in evaluating complex scenarios
• Resilient and composed under pressure and tight deadlines
• Clear communicator with the ability to present findings to diverse audiences
• Ethical and trustworthy with high integrity
• Adaptable and resourceful in a dynamic, tech-driven environment

Additional Requirements:

• Strong references demonstrating investigative skill, objectivity, and operational impact

Attributes: Integrity Guardian

• Protects the business and clients by ensuring claims are accurate, fair, and fraud-free

Evidence Analyst

• Uncovers facts through rigorous investigation and digital analysis

Risk Mitigator

• Identifies and addresses threats to financial and reputational stability

Cross-Functional Collaborator

• Works across teams and disciplines to deliver comprehensive insights

Compliance Champion

• Upholds legal and ethical standards in every investigation

Closing: Tuesday, 29th September 2026.