Chief of Staff

Why project44

At project44 we believe in better.

We challenge the status quo because we know a better supply chain isnt just possibleits 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 youre driven to solve meaningful problems leverage AI to scale rapidly drive impact daily and be part of a high-performance team we should talk.

p44s 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 thats 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 CEOs 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 CEOs 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 project44s 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 CEOs voice and on the CEOs timeline
• Own internal CEO communications: All Hands narratives company-wide messages from the CEOs office and senior leadership updates they deliver personally
• Act as the CEOs proxy in meetings and stakeholder conversations; represent their perspective accurately and with good judgment
• Support the CEOs external agenda: government advisory roles industry conferences media engagements and key investor and customer relationships
• Run the operating rhythm of the CEOs 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 shouldnt happen anywhere else

Head of Operations LSP (50%)

• Implement and drive the operational decision making and cadence between the CEOs office LSP divisional leadership and p44s 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 CEOs office and LSP leadership carry context in both directions prevent surprises and keep the pace matched to how LSPs actually buy: weeks not quarters

Whatyoullneed

• 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. Youve run something not just advised on it.
• 710 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 elses voice. This is essential though itfollows fromoperational 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 torepresentproject44 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 this 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 a 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. Togetherwerebuilding somethingextraordinarylearngrow and thrive in a fast-paced transformative environment.

Diversity & Inclusion

Were 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.

For accommodations during the hiring process please email Even if you dont meet 100% of the qualifications listed you should seriously consider applying.