Chief of Staff

Why project44? At project44, we believe in better. We challenge the status quo because we know a better supply chain isn’t just possible—it’s essential. Better for our customers. Better for their business. Better for the world. Headquartered in Chicago, IL with several other offices worldwide, we are powered by a diverse global team that is tackling the toughest logistics challenges with innovation, urgency, and purpose. If you’re driven to solve meaningful problems, leverage AI to scale rapidly, drive impact daily, and be part of a high-performance team — we should talk. p44’s primary customers are our Shippers - global Fortune 500 brands such as Nike, Ikea and Home Depot. We have recently split our Shippers from our other major customer category – Logistic Service Providers, to be managed directly by the CEO. As a result, this role will essentially be the Chief Operating Officer for our dedicated, AI-native Logistic Service Provider (LSP) division inside project44. The LSP division is being built to win a market that’s moving fast, with the freedom to operate at startup speed on top of an established platform. This role sits at the center of both: directly supporting the CEO on their enterprise agenda and serving as the operational connective tissue between the CEO’s office and the LSP division as it stands up. About the role This is one of the highest-trust, highest-visibility roles in the company: As Chief of Staff to the CEO , you are their primary operating partner — owning their executive agenda, preparing them for every high-stakes engagement, and producing the written output that supports their external and internal voice across a vast array of channels and audiences. As Head of Operations for LSP , you provide the coordination and accountability necessary to provide the coordination and accountability that keeps the LSP division and the CEO's office tightly aligned as we continue the buildout — landing the operating cadence between the two, coordinating shared services, and making sure cross-division work moves at the pace the LSP segment demands. Roughly half the role is CEO-facing. Roughly half is LSP-facing. Both halves require absolute discretion, fast judgment, and an instinct for what actually matters in a given week. This is a high-output, high-trust position for someone who finds operating under unrelenting pressure energizing rather than exhausting. The person who succeeds here can walk into a customer briefing with a global 3PL, hold a peer conversation with a VP of Supply Chain about what project44’s product actually does in their operation, and return to the office and turn that into a crisp executive narrative and polished presentation for a podcast the next day. They are a genuine AI practitioner and super user — someone who uses it to scale their own output every day. What you will own Chief of Staff to the CEO (~50%) Prepare the CEO thoroughly for every high-stakes engagement: board meetings, investor presentations, government advisory sessions, analyst calls, keynote speeches, and executive customer meetings Own the written output that supports those moments — board materials, investor letters, speeches, talking points, op-eds, and briefing documents — in the CEO’s voice and on the CEO’s timeline Own internal CEO communications: All Hands narratives, company-wide messages from the CEO’s office, and senior leadership updates they deliver personally Act as the CEO’s proxy in meetings and stakeholder conversations; represent their perspective accurately and with good judgment Support the CEO’s external agenda: government advisory roles, industry conferences, media engagements, and key investor and customer relationships Run the operating rhythm of the CEO’s office: what the CEO sees, when, in what shape — and follow-through on what he decides Serve as a trusted advisor to the CEO on sensitive matters: leadership team dynamics, talent decisions, and the conversations that shouldn’t happen anywhere else H