Chief of Staff (Onsite - Chicago Office)

Summary

The Chief of Staff role is responsible for supporting the Chief Technology Officer and their leadership team by driving the team's strategic operating rhythm, coordinating cross-functional initiatives, and ensuring the smooth day-to-day operation of the executive's office. This is an individual contributor role reporting directly to the executive, requiring the consistent exercise of discretion and independent judgment on matters of significance to the business. The ideal candidate is equally comfortable building a leadership offsite agenda, synthesizing a complex set of inputs into a clear decision memo, and making independent prioritization decisions that keep the executive and their team focused on what matters most.

Responsibilities

Strategic & Operating Rhythm

• 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.

Cross-Functional Coordination

• 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.

Executive Operations & Strategic Prioritization

• 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.

Reporting & Insights

• Design and maintain reporting frameworks that give the executive visibility into team performance, key metrics, and progress against goals, applying judgment to determine which data points are material and how to surface them.
• Diagnose root causes behind operational friction before proposing solutions — interview stakeholders, identify the real blocker, and recommend fixes that scale beyond a single instance.
• Identify opportunities to improve team processes and operating systems and drive adoption of new tools or practices across the leadership team.
• Other duties and responsibilities as assigned.

Required Knowledge and Skills

• 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).

Education

• 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.