Chief of Staff (Logistics)

TL;DR

Chief of Staff (Logistics/AI): Acting as the primary operating partner to the CEO and Head of Operations for the AI-native Logistic Service Provider (LSP) division with an accent on executive agenda management and operational synchronization. Focus on driving the operational cadence between the CEO's office and the LSP division, producing high-stakes executive communications, and scaling output using generative AI.

Location: Must be based in Chicago, IL (on-site 4 days a week)

Company

A global logistics platform providing visibility and AI-native solutions for Fortune 500 shippers and logistics service providers.

What you will do

• Serve as the CEO's primary operating partner, owning the executive agenda and preparing materials for board meetings, investor presentations, and keynote speeches.
• Lead operations for the LSP division, ensuring tight alignment with the CEO's office and maintaining a fast-paced operating cadence.
• Produce high-quality written output, including op-eds, briefing documents, and internal communications, written in the CEO's voice.
• Act as the CEO's proxy in high-stakes stakeholder conversations and represent the company's perspective with sound judgment.
• Coordinate shared services and operational handshakes between the LSP division and the parent organization.
• Drive cross-division initiatives, tracking decisions and surfacing blockers to ensure rapid execution.

Requirements

• 7–10+ years of experience at the intersection of strategy and operations.
• Domain knowledge in supply chain, logistics, or freight technology.
• Proven track record of personally owning operational outcomes, metrics, and complexity.
• AI-native workflow: daily use of generative and agentic AI tools to scale productivity and solve operational problems.
• Exceptional written communication skills capable of producing board-ready, executive-quality work.
• Prior experience as a Chief of Staff, senior operator, or management consultant with exposure to CEO-level decision-making.

Nice to have

• Direct operator experience in supply chain, logistics, fulfillment, or transportation.
• Background at McKinsey, BCG, Bain, or equivalent firms.
• Financial foundation in investment banking or private equity.
• Experience with board governance, investor relations, or M&A processes.
• Experience at a growth-stage company in the $100M–$500M ARR range.

Culture & Benefits

• High-performance environment characterized by innovation, urgency, and purpose.
• Strong commitment to diversity and inclusion, fostering a world-class experience for a global team.
• Culture centered on in-person partnership and collaboration in the Chicago office to drive faster decision-making.