Chief of Staff to the CEO

project44 • Chicago, IL

15h • Onsite

About The Position

The Chief of Staff is a critical partner to the CEO inside the business. project44 is a complex, AI enabled, global business — and the CEO leads a complex, externally-active agenda: building one of the most important supply chain technology companies in the world while providing input to government bodies on supply chain policy, keynoting major industry events, and driving the business toward its next major milestone. To help drive the business forward, you’ll prepare the CEO for every high-stakes moment, drive the most important cross-functional work, and serve as the connective tissue across a global leadership team. You’ll write in his voice, represent his perspective, and make sure the most important things actually get done. This is a high-output, high-trust position for someone who wants to be at the center of a consequential company at a critical point in its growth. The biggest single requirement is writing — board materials, investor updates, keynote speeches, op-eds, government briefings, All Hands narratives — all to a standard that requires minimal editing, all in the CEO’s voice.

Requirements

• Exceptional written communication skills — the most important requirement in this role. You need to produce board-ready, publication-quality work quickly, and to do so in someone else’s voice
• 5-10 years of experience at the intersection of strategy and execution in a fast-moving environment — some combination of top-tier strategy consulting, finance, and senior operator experience
• Prior experience as a Chief of Staff, senior strategy 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 meeting, government briefing, analyst call, or media appearance
• High EQ and sound judgement, particularly around sensitive information and complex interpersonal situations
• Structured thinking that brings clarity to complexity without adding bureaucracy
• 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’re looking for someone who finds that energizing
• Demonstrated ability to leverage generative and agentic AI tools in your work — with the judgment to direct them effectively, evaluate outputs critically, and apply them responsibly.

Nice To Haves

• Experience in supply chain or, logistics technology, or supply chain — as an operator, consultant, or investor
• 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 fluency
• Prior experience supporting a CEO with a significant external agenda: government, media, or investor relations
• Exposure to board governance, investor relations, or M&A processes
• Experience at a company in the $100M–$500M ARR range navigating the challenges of transformation and scaling

Responsibilities

• Own the CEO’s operating rhythm: priorities, time allocation, and the tracking of leadership team commitments
• Run the cadence of the senior leadership team — staff meetings, OKR reviews, annual planning, and executive off-sites — ensuring they drive real decisions, not just attendance
• Serve as connective tissue between the CEO and C-suite: surface blockers early, track what has been decided, and follow through on what has not
• Prepare the CEO thoroughly for every high-stakes engagement, including: Board meetings, investor presentations, and shareholder communications; Government advisory meetings and policy briefings; Analyst and media engagements, panel appearances, and keynote speeches; Executive customer meetings and major industry events
• Own the written output that supports these moments: board packs, investor letters, speeches, talking points, op-eds, and briefing documents — all in the CEO’s voice and with strong design skills
• Own internal CEO communications: All Hands narratives, company-wide emails, and senior leadership messages
• Lead high-priority cross-functional projects that don’t sit neatly within a single function, including market analysis, competitive response, M&A diligence support, and strategic operational initiatives
• Act as the CEO’s proxy in meetings and stakeholder conversations; represent his perspective accurately and with good judgement
• Synthesize information from across the business and surface the most important issues to the CEO before they become problems
• Partner with the exec team to ensure cross-functional work has the right sponsorship, resourcing, and accountability to land
• Support the CEO’s external agenda: government advisory roles, industry conferences, media engagements, and key investor and customer relationships
• Serve as a trusted confidant on sensitive matters including talent, culture, leadership team dynamics, and org design
• Maintain the pulse of the organization — understand morale and emerging issues and give the CEO an honest, unfiltered read

Benefits

• We’re focused on creating a company where all team members can bring their authentic selves to work every day.
• project44 is an equal opportunity employer seeking to enrich our work environment by creating opportunities for individuals of all backgrounds and experiences to thrive.
• For any accommodations needed during the hiring process, please email [email protected].
• Even if you don’t meet 100% of the role requirements, you should still seriously consider applying. Studies show that candidates can still be considered for a role if they meet just 50% of the requirements.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed