Staff Manager

Location: Chicago, IL (On-site)
Employment Type: Full-Time
Compensation: $80,000–$90,000 Total Compensation

Benefits: Health Insurance, Dental Insurance, Vision Insurance, Life Insurance, 401(k), Paid Time Off (PTO), and Paid Sick Leave.
Reports To: 

Work Authorization: Applicants must be authorized to work in the United States on a full-time basis.

About Performance AI

Performance AI helps organizations transform the way they operate through AI-powered solutions that improve efficiency, automate workflows, and drive measurable business outcomes. We partner with healthcare organizations, enterprise clients, and high-growth businesses to design and implement enterprise AI solutions.

We're looking for a highly organized, proactive, and execution-focused Chief of Staff to work directly alongside our CEO. This is not a traditional strategic Chief of Staff role. Instead, you'll serve as the CEO's trusted operational partner, creating structure, driving execution, and ensuring critical business priorities move forward.

Position Overview

The Chief of Staff serves as the CEO's operational right hand, managing executive operations, business administration, and cross-functional execution so leadership can focus on customers, strategy, and company growth.

Key Responsibilities

Executive Operations

• Manage the CEO's calendar, scheduling, priorities, and daily workflow.
• Prepare meeting agendas, capture meeting notes, and track action items.
• Draft professional emails, executive communications, and follow-up correspondence.
• Proactively provide periodic updates on priorities, commitments, and potential blockers.

Executive Travel & Logistics

• Coordinate domestic and international travel, including flights, accommodations, ground transportation, visas (when applicable), itineraries, and meeting logistics.
• Prepare travel schedules, executive briefings, presentations, and supporting materials.
• Coordinate logistics for customer visits, conferences, workshops, speaking engagements, and business events.
• Anticipate and resolve scheduling or logistical conflicts before they impact business operations.

Business Administration

• Prepare, edit, and coordinate contracts, proposals, NDAs, invoices, and executive business documents.
• Manage PTO tracking, employee hours, and administrative records using company systems.
• Maintain organized legal, financial, and operational documentation.
• Ensure all business documents meet company branding and quality standards.

Project & Operational Coordination

• Maintain operational dashboards, trackers, SOPs, workflows, and documentation.
• Coordinate cross-functional initiatives and monitor progress across departments.
• Identify risks, remove blockers, and escalate issues when appropriate.
• Recommend process improvements that increase operational efficiency, accountability, and scalability.

Leadership & Relationship Support

• Coordinate communication between leadership, customers, vendors, investors, and business partners.
• Support executive recruiting coordination, interview scheduling, and onboarding activities.
• Represent the company professionally during customer meetings, business dinners, conferences, and industry events as needed.

Required Qualifications

• 5+ years of experience supporting founders, CEOs, or C-level executives.
• Experience in executive support, business operations, project coordination, or startup operations.
• Exceptional written and verbal English communication skills.
• Strong organizational, project management, and prioritization skills.
• Proven ability to manage multiple high-priority initiatives simultaneously.
• Experience preparing executive-level contracts, proposals, presentations, and business documentation.
• Proficiency in Google Workspace and Microsoft Office.
• Experience with business systems such as HubSpot, Gusto, DocuSign, QuickBooks, or similar platforms.
• Comfortable using AI tools such as ChatGPT, Gemini, Claude, and similar technologies to improve productivity and business operations.
• Willingness to travel as business needs require.

Preferred Qualifications

• Experience working in a startup or high-growth environment.
• Experience supporting multiple business functions.
• Experience coordinating executive travel, customer meetings, and business events.
• Familiarity with process improvement and operational systems.

What We're Looking For

At Performance AI, we believe technical skills can be developed, but character is what drives long-term success. We're looking for someone who not only has the experience to succeed but also brings the professionalism, judgment, and ownership needed to become a trusted partner to executive leadership.

The ideal candidate is someone who:

• Takes complete ownership of responsibilities and consistently follows through on commitments.
• Proactively provides periodic status updates without being asked, ensuring leadership always has visibility into priorities, progress, and potential blockers.
• Communicates professionally, clearly, and confidently with executives, customers, vendors, and business partners.
• Naturally creates structure from ambiguity and enjoys organizing complex situations.
• Anticipates needs and thinks several steps ahead.
• Exercises excellent judgment and handles confidential information with professionalism and discretion.
• Thrives in a fast-paced environment where priorities change quickly and can confidently shift between strategic coordination and hands-on execution.
• Builds trust through reliability, consistency, and exceptional follow-through.
• Uses AI tools thoughtfully to improve productivity while maintaining critical thinking and sound judgment.
• Represents Performance AI with professionalism, integrity, and executive presence.

Success Measures

Success in this role is measured by:

• Leadership always has visibility into priorities, commitments, and project status.
• Business operations, executive logistics, and documentation are executed accurately and on time.
• Operational processes become increasingly organized, scalable, and efficient.
• The CEO spends significantly less time on operational coordination and more time focused on customers, strategy, and company growth.

Why Join Performance AI?

At Performance AI, you'll work directly alongside the CEO and play a critical role in helping the company operate with greater structure, speed, and accountability. You'll remove operational friction, improve execution, and build scalable systems that enable leadership to focus on customers, innovation, and long-term growth.