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Supply Chain Management, Logistics, Software Development, Transportation

Chief of Staff to CEO

Chicago, ILOnsiteFull TimeChief / Executive$180,000–$200,000 /yrPosted 1 day agoVisa sponsorship available

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Required skills

  • AI tools
  • AI workflows
  • prompt writing
  • content drafting
  • narrative development
  • information triage
  • executive office
  • brand
  • narrative
  • editorial

Nice to have

  • complex technical B2B SaaS
  • journalism
  • corporate communications
  • product marketing
  • portfolio
  • executive narrative

Role summary

The Chief of Staff to the CEO is a critical role focused on communications, brand, and narrative, reporting directly to the Founder & CEO. You will act as a trusted partner and editorial lead, refining the CEO's communications and executive office materials for various audiences including the company, press, and customers. This position demands exceptional writing, editorial skills, sharp judgment, and fluency in brand and product marketing. You will embody the CEO's voice, ensuring consistency across all channels. Leveraging AI tools inventively to enhance output and streamline executive operations is expected. Responsibilities include final editorial review of high-stakes written materials, guardianship of the brand narrative, partnership with Product Marketing, building the CEO's external thought-leadership presence, driving executive alignment, acting as a strategic information filter, embedding AI tools into office workflows, and managing sensitive special projects. A Bachelor's degree and 7+ years of experience in communications, product marketing, brand strategy, corporate communications, or a previous Chief of Staff role in a fast-scaling B2B environment are required. Direct experience in logistics, supply chain, freight, or transportation technology is also required. The role requires being on-site in Chicago 4 days per week.

About the role

The Chief of Staff to the CEO is a high-impact, high-visibility role built around communications, brand, and narrative. Reporting directly to the Founder & CEO, you will serve as a trusted partner and editorial right hand – reviewing, sharpening, and helping prepare the CEO's communications and the executive office's most important materials before they reach their audience, whether that's the company, the press, or a customer.

This position requires someone with exceptional writing and editorial instincts, sharp judgment, and full fluency in brand and product marketing craft. You will act as a close partner to the CEO's voice – reviewing drafts, tightening narrative, and ensuring consistency across every channel the CEO and company show up in. At project44, leveraging AI is a company-wide expectation, and the Chief of Staff must use these tools fluently and inventively to compound their output, sharpen executive content, and drive the rhythm of the executive office.

Responsibilities

  • Document & Communications Review: Serve as the final editorial check on the executive office's highest-stakes written materials – press releases, bylines, media Q&A, and board and leadership presentations – reviewing drafts, resolving open comments, and ensuring everything is clear, accurate, and ready before it reaches the CEO or its intended audience.
  • Brand & Narrative Stewardship: Serve as a guardian of project44’s brand narrative and messaging framework, ensuring consistency across product launches, company announcements, and the CEO’s public presence.
  • Product Marketing Partnership: Partner closely with Product Marketing and Marketing leadership to shape the story behind major product and company announcements, ensuring the CEO’s voice and company positioning are woven through every go-to-market narrative.
  • Executive Content & Thought Leadership: Build and manage the CEO’s external thought-leadership presence – bylines, keynotes, panels, press interviews, and social platforms – that reinforce project44’s category leadership.
  • Executive Alignment: Partner closely with the Executive Leadership Team (ELT) to capture key decisions, drive cross-functional alignment, and track follow-through on the CEO’s top communications and brand priorities.
  • Information Triage: Act as a strategic filter for the Office of the CEO. Triage inbound requests and exercise high-level judgment to determine what requires the CEO’s direct attention versus what can be resolved independently or routed elsewhere.
  • AI Tooling & Workflows: Embed modern AI tools into the core of how the Office of the CEO operates. Build AI workflows, write effective prompts, and critically evaluate output to accelerate content drafting, narrative development, and information triage.
  • Special Projects: Manage the CEO’s most sensitive, time-critical communications and brand projects from end to end.

    • Qualifications

  • You have 7+ years of experience in communications, product marketing, brand strategy, corporate communications, or a previous Chief of Staff role within a fast-scaling B2B environment.
  • You possess exceptional writing skills and can seamlessly adapt your style to draft compelling content in the CEO’s voice, across formats from a keynote to a customer-facing byline.
  • Your sharp instincts span brand, product marketing, and go-to-market storytelling, so you can act as an effective sounding board and editor for executive and company narrative.
  • You are deeply fluent with modern AI tools and use them as a core part of how you work. You build personal AI workflows, write effective prompts, and evaluate output.
  • You possess strong command of modern presentation and content tools, and are able to translate complex ideas into compelling, executive-ready narrative and visuals.
  • You exercise impeccable judgment and absolute discretion when managing highly sensitive or confidential information.
  • You have a proven track record of executing quickly and thriving in the fast-paced and intense environment of an executive office.
  • A Bachelor’s degree is required.
  • You have direct, hands-on experience in logistics, supply chain, freight, or transportation technology.

    • Preferred Skills

  • You have experience operating within a highly complex, technical B2B SaaS ecosystem.
  • You have a background in journalism, corporate communications, or product marketing, with a portfolio of executive or brand narrative work you’re proud of.
  • You exhibit a high degree of comfort navigating ambiguity and can autonomously drive outcomes even when executive priorities rapidly shift.
  • You bring exceptional emotional intelligence and executive presence, enabling you to build trust quickly with media, industry analysts, customers, and the broader leadership team.
  • You have direct experience partnering with product marketing or brand teams on major company or product launches.

    • Our target compensation range for this role is $180,000 - $200,000 plus annual bonus eligibility. Candidates must be willing to be on-site in our Chicago office 4 days per week.

    Diversity & Inclusion

    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 are building for. So it’s up to us to create a company where anyone can bring their authentic self to work every day. We’re constantly working to improve, and we accept our responsibility to elevate the voices left in the margins. It’s on every one of us.

    Our focus on inclusion manifests in the way we hire, the customers we serve, and the regions we prioritize. We’re building a company that every one of us at project44 is proud to work for: a company that celebrates you for being you.

    We pride ourselves on celebrating everyone — project44 is an equal opportunity employer actively working on creating a diverse and inclusive work environment where underrepresented groups can 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 needed accommodations during the hiring process, please email recruiting@project44.com. Even if you don’t meet 100% of the above qualifications, you should still seriously consider applying. Studies show that you can still be considered for a role if you meet just 50% of the role’s requirements.

    More about project44

    Since 2014, project44 has been transforming the way one of the largest, most important global industries does business. As transportation and logistics continues to evolve and customer expectations around delivery become more demanding, industry technology must rise to the occasion. In just a few short years, we’ve created a digital infrastructure that eliminates the inefficiencies caused by dated technology and manual processes. Our Advanced Visibility Platform is used by the world’s leading brands to track shipments, collaborate with supply chain partners, drive operational efficiencies, and create outstanding customer experiences.

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