Chief of Staff (AI-Enabled CEO Operations Partner)

AJAIA; Miami (FL); On-site; USD 120,000 - 190,000; Full time

Job summary

Ajaia is seeking a Chief of Staff to elevate the CEO’s decision velocity and execution across multiple companies. You will centralize initiatives, maintain dashboards, and surface actionable insights using AI in daily workflows.

The role emphasizes cross‑functional alignment, strategic planning, and rigorous accountability to deliver high-impact outcomes. Ideal candidates have strong organizational and analytical skills, experience with multi‑company operations, and proficiency with modern

Qualifications

• Experience coordinating multiple complex initiatives across units and teams.
• Ability to create visibility into priorities, risks and decisions.
• Proven track record in executive support and cross-functional alignment.

Responsibilities

• Coordinate enterprise-level initiatives across business units and companies.
• Own and maintain the CEO central operating dashboard and reporting.
• Prepare executive briefings, memos, and decision materials.
• Drive accountability and track milestones, dependencies, and ownership.
• Identify blockers and unblock progress to sustain momentum.
• Enable AI-driven workflows and automation across functions.

Skills

Organizational skills

Project management

Strategic thinking

Business judgment

Communication

Ambiguity handling

Tools

Notion

ClickUp

Coda

Airtable

Asana

Monday.com

Job description

About the Company

Ajaia is a rapidly growing AI consultancy and product studio dedicated to helping organizations move from experimentation to real results. We operate across four core pillars: AI Strategy and Advisory, AI Engineering and Automation, Workforce Training and Enablement, and Custom Product Development.

In addition to client services, Ajaia builds proprietary AI products, copilots, and vertical solutions that solve high-value industry problems. This dual model allows us to translate hands‑on implementation experience into scalable products while continuously refining our approach through real‑world deployment.

Our operating model combines deep technical execution with practical change management, enabling enterprises to deploy secure, compliant, and high‑impact solutions that drive measurable operational value. From executive roadmapping to production‑ready systems and workforce upskilling, Ajaia embeds intelligent tools directly into the workflows that matter most.

Mission: Help organizations win the AI moment.

Position Overview

Our client is looking for a Chief of Staff to increase the CEO’s decision velocity, execution throughput, and organizational leverage by creating visibility, accountability, and operational excellence across all key initiatives. The Chief of Staff will function as the central coordination point across multiple companies, initiatives, leadership teams, strategic projects, and external stakeholders.

We expect candidates to use AI in daily workflows across research, ideation, drafting, design iteration, quality checks, and delivery acceleration. AI usage is a core execution requirement, not optional tooling.

Job Requirements

Strategic Execution & Initiative Management

• Manage enterprise-level initiatives across multiple business units and companies.
• Maintain visibility into all strategic priorities, projects, and commitments.
• Track milestones, deliverables, dependencies, and ownership.
• Identify stalled initiatives and proactively unblock progress.
• Ensure leadership teams remain aligned around strategic objectives.
• Drive accountability across cross‑functional stakeholders.

CEO Operating System Management

• Own and maintain the CEO’s central operating dashboard.
• Build and manage executive reporting frameworks.
• Maintain initiative roadmaps and execution trackers.
• Develop systems for monitoring organizational performance.
• Create clear visibility into priorities, risks, and decisions requiring executive input.
• Ensure no critical commitment or follow‑up falls through the cracks.

Decision Support

• Prepare executive briefings and decision memos.
• Synthesize information from multiple stakeholders.
• Conduct research and analysis to support strategic decisions.
• Surface risks, trade‑offs, and recommendations.
• Filter noise and prioritize the highest‑impact issues.

Leadership Coordination

• Coordinate communication across executive and leadership teams.
• Facilitate follow‑up on leadership meetings.
• Ensure decisions are documented and implemented.
• Align stakeholders on objectives, timelines, and accountability.
• Support strategic planning sessions and quarterly reviews.

Performance & KPI Management

• Establish and monitor key performance indicators.
• Track progress against company objectives.
• Develop executive‑level reporting and dashboards.
• Identify trends, opportunities, and areas requiring intervention.
• Provide regular updates on strategic initiative performance.

AI & Automation Enablement

• Leverage AI tools to improve executive productivity.
• Implement workflows that convert meetings into actionable tasks.
• Improve reporting, documentation, and information flow.
• Evaluate opportunities for automation across business functions.
• Help build scalable operating systems supported by AI and data.

Executive Support During Travel & Events

• Capture discussions, commitments, and action items.
• Coordinate follow‑ups with investors, partners, executives, and stakeholders.
• Maintain continuity and execution momentum while the CEO is traveling.
• Ensure critical decisions and communications are documented and tracked.

Technical Requirements

• Exceptional organizational and project management skills.
• Strong business judgment and problem‑solving ability.
• Ability to operate effectively in ambiguity.
• Excellent written and verbal communication skills.
• Experience managing multiple complex projects simultaneously.
• Strong analytical and operational mindset.
• High ownership and accountability.
• Ability to influence without formal authority.
• Proficiency with modern productivity and collaboration tools.

Preferred Requirements

• Previous experience as a Chief of Staff, Strategy Manager, Operations Lead, Program Manager, Management Consultant, Founder, or Senior Operator.
• Experience working directly with founders, CEOs, or executive teams.
• Familiarity with AI tools and workflow automation.
• Experience managing cross‑company or multi‑business operations.
• Experience with Notion, ClickUp, Coda, Airtable, Asana, Monday.com, or similar systems.

Salary and total compensation depend on experience, portfolio strength, and demonstrated performance during the hiring process.