Chief of Staff (Onsite - Chicago Office)

Responsibilities

• Own the leadership team's operating cadence — staff meetings, leadership offsites, quarterly business reviews — including agenda-setting, pre-reads, facilitation support, and follow-up on action items.
• Partner with the executive to translate strategic priorities into a clear set of goals and workstreams; track progress and surface risks or slippage before they become problems.
• Prepare board-ready and leadership-ready materials — decks, briefing documents, and talking points — that distill complex or ambiguous input into clear, decision-ready narratives.
• Serve as a thought partner to the executive, pressure-testing ideas and providing an independent perspective grounded in data and cross-functional context.
• Act as a trusted liaison between the executive's office and other functions (Finance, HR, IT, Legal, Product, Engineering), ensuring alignment and unblocking cross-team dependencies.
• Drive follow-through on cross-functional initiatives on the executive's behalf, independently assessing progress, holding workstream owners accountable, and making escalation decisions when deadlines are at risk.
• Coordinate special projects that fall outside the scope of any single team, scoping the work, assembling the right stakeholders, and driving it to completion.
• Build rapport across the organization to effectively bridge communication between the executive and others internally and externally, operating with tact and discretion.
• Exercise independent judgment to strategically prioritize the executive's time across competing demands, evaluating the relative importance of internal and external commitments and making access decisions that align with organizational priorities.
• Plan and direct key meetings and offsites, including determining format, content flow, and participant selection, and coordinating with internal and external stakeholders to execute logistics.
• Develop and shape executive communications, presentations, and written updates, exercising judgment on messaging, tone, and strategic framing for senior audiences.
• Maintain full awareness of company initiatives and priorities in order to exercise independent authority to act on the executive's behalf in their absence and provide cross-functional leadership support as needed.

Requirements

• 5+ years of experience in a chief of staff, strategy, operations, management consulting, or senior business advisory role, ideally within a B2B SaaS or technology environment.
• Demonstrated ability to manage multiple, competing workstreams simultaneously with strong organization and follow-through.
• Track record of driving alignment and execution across teams without direct authority.
• Strong written and verbal communicator, able to translate ambiguous or complex information into clear, senior-audience-ready materials.
• Highly proactive, resourceful, and comfortable operating with a high degree of discretion and confidentiality.
• Comfortable with ambiguity; able to sequence and prioritize work in a fast-changing environment with high-level direction.
• Proficient with standard productivity and collaboration tools (Microsoft Office/Google Workspace, project trackers, AI tools such as ChatGPT or Claude).

Qualifications

• A bachelor's degree is required (or equivalent combination of education and experience).
• Advanced degree such as an MBA or related field is preferred but not required.