Chief of Staff

project44; Chicago (IL); On-site; USD 150,000 - 200,000; Full time

Job summary

project44 is seeking a Chief of Staff to the CEO in Chicago. This leadership role involves preparing the CEO for crucial engagements and driving operational decisions within the LSP division, ensuring alignment with the overall leadership team.

The ideal candidate has extensive experience in strategy and operations, with strong communication skills and a solid background in supply chain management. The position requires on-site collaboration four days a week, fostering innovation and quick decision-making.

Qualifications

• 7–10+ years of experience in strategy and operations.
• Experience as a Chief of Staff or senior operator.
• Genuinely AI-native, understanding the use of AI tools.

Responsibilities

• Prepare CEO for high-stakes engagements.
• Drive operational decisions between divisions.
• Communicate context between CEO's office and LSP leadership.

Skills

Supply chain knowledge

Operational execution

Strong written communication

High EQ and judgment

Discretion and integrity

Job description

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 keep 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 ensuring cross‑division work moves at the pace the LSP segment demands.

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 conversations that shouldn’t happen anywhere else

Head of Operations, LSP (~50%)

• Implement and drive the operational decision making and cadence between the CEO’s office, LSP divisional leadership and project44’s overall leadership team: weekly check‑ins, board prep, ELT updates, and the rhythm that keeps the CEO and the LSP team tightly connected
• Coordinate the services agreement interface between the LSP division and the project44 parent: shared platform, hosting, data graph, back‑office services—making sure the operational handshakes work and escalations land in the right place
• Land cross‑division initiatives that have direction set by LSP leadership or the CEO—driving execution, tracking decisions, surfacing blockers, and following through. This role implements and coordinates; LSP leadership owns LSP outcomes
• Prepare CEO‑facing LSP materials: division updates for Board reviews, ELT readouts, and the cross‑company conversations that keep Shipper and LSP aligned
• Communicate between the CEO’s office and LSP leadership—carry context in both directions, prevent surprises, and keep the pace matched to how LSPs actually buy: weeks, not quarters

What you’ll need

• Supply chain, logistics, or freight technology domain knowledge—enough to hold a peer conversation with a VP of Supply Chain or operations leader at a global shipper, 3PL, or carrier. This is the most important requirement in this profile and while not absolutely necessary will make your candidacy much more competitive.
• Operational execution track record—you have personally owned operational outcomes, metrics, and complexity. You’ve run something, not just advised on it.
• 7–10+ years of experience at the intersection of strategy and operations, with clear progression toward higher‑stakes, more consequential roles
• Genuinely AI‑native: you use generative and agentic AI tools in your own workflow every day, you understand their limits, and you can apply them to operational and communications problems
• Strong written communication—you produce board‑ready, executive‑quality work quickly and in someone else’s voice. This is essential, though it follows from operational depth rather than preceding it.
• Prior experience as a Chief of Staff, senior operator, or management consultant with direct exposure to CEO or founder‑level decision‑making
• Executive presence and the credibility to represent project44 in any setting: board room, government briefing, analyst call, or customer meeting
• High EQ and sound judgment—particularly around sensitive information, leadership team dynamics, and complex interpersonal situations
• Absolute discretion and integrity—the role carries access to the most sensitive information and conversations in the company
• Drive and resilience—this is a high‑output role with a high‑expectation principal, and we are looking for someone who finds that energizing

What Will Make You Stand Out

• Direct operator experience in supply chain, logistics, fulfillment, or transportation—you have run operations, not just advised on them
• Background at McKinsey, BCG, Bain, or equivalent with subsequent operator role at a growth‑stage company
• Finance foundation—investment banking or private equity—with strong analytical and financial modeling fluency
• Experience supporting a CEO with a significant external agenda: government, Senate, media, or major investor relationships
• Exposure to board governance, investor relations, or M&A processes as a direct participant, not in a supporting role
• Experience at a company in the $100M–$500M ARR range navigating the challenges of transformation, scaling, or market expansion

In office connection

Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for a leader who is enthusiastic and committed to joining our team on‑site in Chicago four days a week. This role benefits from in‑person partnership, faster decision‑making, and close collaboration with business and functional leaders.

Diversity & Inclusion

We’re designing the future of how the world moves and is connected through global trade and supply chains. We can only build a world‑class product and experience if our teams are as diverse as the communities we serve. project44 is an equal‑opportunity employer actively working to create a diverse and inclusive work environment.