Chief of Staff - Part time

Location: Remote – South Africa

Working Hours: US Business Hours Part time (3:00 PM onwards SA Time)
Employment Type: Independent Contractor
Must have your own laptop

We are seeking a versatile, strategic, and tech-savvy Chief of Staff to join our team in a part-time capacity.You will act as a trusted advisor to leadership, optimizing internal operations while safeguarding the business legally. The absolute core of this position is high-stakes, empathetic conflict resolution, specifically navigating sensitive customer, vendor, and pricing disputes. You will blend legal acumen with financial pragmatism to find win-win resolutions, all while leveraging cutting-edge AI tools to scale your efficiency.

Key Responsibilities

• Take ownership of critical escalations and customer disputes (e.g., resolving friction when a parcel arrives with unexpected costs and the customer cannot pay).
• Analyze the financial impact of disputes to design creative, empathetic, and commercially viable resolutions that protect company margins while maintaining goodwill.
• Review, draft, and optimize commercial contracts, vendor agreements, and Terms of Service across non-US or international jurisdictions.
• Actively implement and utilize AI tools (such as LLMs and automation prompts) to streamline workflows, draft rapid legal responses, and scale operational efficiency.
• Act as a strategic problem-solver to resolve friction between customers, logistics partners, and internal leadership.

Requirements

• Legal knowledge
• Background in mediation, customer arbitration, or crisis management with a proven ability to de-escalate high-tension situations.
• Strong understanding of foundational business metrics (e.g., margins, write-offs, and lifetime value) to make calculated settlement decisions.
• Daily, hands-on experience utilizing generative AI tools (e.g., ChatGPT, Claude) for writing, contract analysis, and workflow acceleration.