Chief of Staff to the CEO at project44 in Chicago, IL

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. With our Decision Intelligence Platform, Movement, we’re redefining how global supply chains operate. By transforming fragmented logistics data into real-time, AI-powered insights, we empower companies to connect instantly, see clearly, act decisively, and automate intelligently. Our Supply Chain AI enhances visibility, drives smarter execution, and unlocks next-gen applications that keep businesses moving forward. Headquartered in Chicago, IL with a 2nd HQ in Bengaluru, India 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. About the role 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. What you’ll do 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 What you’ll need 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. What Will Make You Stand Out 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 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. Together, we’re building something extraordinary—learn, grow, and thrive in a fast-paced, transformative environment. Diversity & Inclusion At project44, we’re designing the future of how the world moves and is connected through trade and global supply chains. We can only deliver a truly world-class product and experience if our teams are as diverse and unique as the communities we serve. 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. If you share our values and our passion for helping the way the world moves, we’d love to review your application. For any accommodations needed during the hiring process, please email recruiting@project44.com. 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.