Our client is a high profile, multi industry entrepreneur who leads several ventures simultaneously, sits on corporate and nonprofit boards, and maintains an active public platform through media, speaking engagements, and published work. She is seeking a Chief of Staff: someone who has operated at this altitude before, understands the pace and complexity of a multi company entrepreneur's world, and can take real ownership of priorities, projects, and follow through across the portfolio.
This is not an administrative role. The right person has already partnered with a principal at this level, anticipates needs before they are voiced, thinks several steps ahead, and is comfortable driving clarity and execution across several businesses at once.
Key Responsibilities
- Act as a strategic partner and force multiplier to the executive, translating her priorities into action across multiple companies and initiatives.
- Oversee and orchestrate a complex, shifting calendar across companies, board commitments, and speaking engagements, with the judgment to anticipate conflicts and prep needs well in advance.
- Own communications triage and follow through at a portfolio level, filtering what needs her attention, resolving what does not, and ensuring nothing across the businesses is dropped.
- Drive active projects to completion, using tools such as Gantt charts to manage timelines, vendors, and deliverables across multiple initiatives and workstreams.
- Support an active capital raise, working directly with the investor relations lead to keep documentation, follow ups, and communications moving forward.
- Lead board meeting logistics and preparation end to end, ensuring materials, briefings, and her time are handled with precision.
- Own speaking engagement logistics from end to end, coordinating with speaker bureaus, event organizers, and travel.
- Serve as a proactive communicator to the executive and across her teams, delivering short, clear briefs rather than requiring status to be chased.
- Build and manage vendor and supplier relationships as new projects or ventures require, acting as an extension of the executive in these dealings.
Requirements
- 5+ years in a Chief of Staff, senior executive support, or right hand role to a C level executive, founder, or entrepreneur, ideally across multiple entities or a fast moving portfolio of businesses.
- Demonstrated ownership of an executive's calendar, communications, and project pipeline with minimal oversight; a track record of taking things off someone's plate and seeing them through.
- Strong organizational and project management instincts; experience with tools like Gantt charts or similar tracking systems is a plus.
- Sound judgment and discretion, with the ability to prioritize and make calls independently in a high volume, fast paced environment.
- Exposure to investor relations, fundraising support, board administration, or speaking and PR coordination is a strong plus.
- Comfortable operating as a true partner to a founder who moves quickly, someone who keeps pace rather than needing to be managed.
- Prior experience supporting an entrepreneur in a build phase (multiple ventures, high growth) preferred; restaurant, hospitality, or media industry exposure is a plus but not required.
Chief of Staff in chicago at Unknown Company
This position is listed as full time and onsite.