Chief of Staff
Waterstone Human Capital · Chicago, IL · 1 wk ago
HybridAdministrativeFull-time
About the Role
Our client, a high-profile, multi-industry entrepreneur, is seeking a Chief of Staff to partner with her in managing a complex portfolio of ventures, board commitments, and public engagements. This role requires someone who has operated at a high level 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 ideal candidate has already partnered with a principal at this level, anticipates needs, thinks ahead, and drives clarity and execution across multiple businesses.
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, anticipating 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.