Executive Ops Lead for AI Transformation

The Cool Company; Miami (FL); Hybrid; USD 140,000 - 210,000; Full time

Job summary

The COOL company is seeking a Chief of Staff & AI Integration to work directly with the Founder & CEO. This high-trust, hands-on operator will translate CEO priorities into accountable execution while leading practical, secure AI adoption across our businesses. Will partner with the CTO, leaders, and People Team; not replace ownership.

You will design AI-enabled workflows, ensure governance, and move pilots into durable production with measurable results, reporting to the CEO.

Qualifications

• 6+ years in high-ownership business operations, chief of staff, strategy and operations, consulting, product operations, or automation/transformation roles.
• Demonstrated record of shipping cross-functional changes and building reliable operating processes.
• Hands-on fluency with AI products, LLM workflows, automation platforms, APIs/integrations, and data systems.

Responsibilities

• Own the CEO's strategic operating cadence, priorities, and status updates.
• Convert discussions into a prioritized action register with owners and deadlines.
• Design, prototype, and deploy AI-enabled workflows with secure integrations.

Skills

Executive operations

AI/LLM workflows

Cross-functional leadership

Project management

Security/confidentiality

Tools

CRM platforms

Spreadsheet tools

Project management tools

Job description

The COOL company is seeking a Chief of Staff & AI Integration to work directly with the Founder & CEO. This high-trust, hands-on operator will translate CEO priorities into accountable execution while leading practical, secure AI adoption across our businesses. Will partner with the CTO, leaders, and People Team; not replace ownership.

You will design AI-enabled workflows, ensure governance, and move pilots into durable production with measurable results, reporting to the CEO.