Chief of Staff & AI Integration

the COOL company • Miami, FL

23h

About The Position

The COOL Company is seeking a high-trust, hands-on operator to work directly with the Founder & CEO. The role turns CEO priorities into accountable execution while leading practical, secure AI adoption across the company’s businesses. It sits at the intersection of executive operations, strategic projects, data, technology, and change management. The Chief of Staff & AI Integration translates decisions into clear owners and deadlines, removes cross-functional bottlenecks, designs and deploys AI-enabled workflows, and demonstrates their business impact. The role partners with the CTO, functional leaders, and the People Team; it does not replace functional ownership, act as the CTO, or independently commit the company to external actions.

The company operates across media, creative AI, advertising technology, publisher monetization, and other growth initiatives. The role will help build a repeatable operating system that advances important work faster, reduces handoffs, and improves visibility. The initial priority is implementing useful AI workflows that employees adopt, save measurable time, improve decisions and follow-through, and maintain strong data-security controls.

The role owns the CEO’s strategic operating cadence and selected cross-functional initiatives, and audits, designs, prototypes, implements, and monitors secure AI workflows. It works with the CTO and security owners on access, permissions, privacy, vendor selection, data retention, accuracy checks, and human approval gates. Successful workflows are developed into durable production processes with documentation, exception handling, monitoring, training, assigned owners, and measurable results.

The position reports to the Founder & CEO and is a senior individual contributor / executive operator role. Miami or New York is preferred, with regular in-person collaboration and travel as needed; the final arrangement is subject to approval. Employment is full-time. Compensation and benefits are a competitive package to be finalized by the CEO and People Team; company benefits and any incentive or equity eligibility will be confirmed during recruiting.

Requirements

• At least 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, not just advising on them.
• Hands-on fluency with current AI products, LLM workflows, automation platforms, APIs/integrations, and data systems; ability to prototype personally and work with engineers on production-grade implementations.
• Strong command of CRM, spreadsheets, dashboards, project management, meeting intelligence, and structured documentation.
• High analytical rigor, including ability to define baselines, evaluate ROI, measure adoption, and investigate inaccurate or misleading outputs.
• Exceptional written communication, project management, prioritization, stakeholder leadership, and executive judgment.
• Sound security and confidentiality instincts, including understanding of human-in-the-loop approvals and sensitive-data handling.
• Calm under ambiguity, discreet, curious, resourceful, low-ego, and comfortable holding senior leaders accountable.
• Personally executes and takes end-to-end ownership; reports status transparently, gives candid feedback, and escalates issues promptly.
• Relentlessly improves systems and challenges inefficient defaults, while treating colleagues as partners and designing workflows that help them succeed.

Nice To Haves

• Meaningful experience partnering with a founder or executive team is strongly preferred.
• Experience in advertising, media, or MarTech is a plus, but not a prerequisite.

Responsibilities

• Own the CEO’s strategic operating cadence, including weekly priorities, leadership follow-ups, meeting preparation, decision logs, and status updates.
• Convert CEO and leadership discussions into a prioritized action register with owners, deadlines, dependencies, and escalation paths, and follow through to completion.
• Prepare concise executive briefs using approved sources such as CRM, meetings, project systems, and communications; distinguish facts, assumptions, and recommendations.
• Surface missed commitments, risks, and cross-functional bottlenecks early, and push for decisions without creating unnecessary meetings.
• Audit high-friction workflows across Sales, Account Management, Marketing, Product, Engineering, Finance, People, and Operations; prioritize use cases by impact, feasibility, risk, and adoption.
• Design, prototype, and implement secure AI workflows using approved tools and integrations, including meeting-to-action systems, reporting, CRM hygiene, knowledge retrieval, and repetitive process automation.
• Work with the CTO and security owners on system access, permissions, privacy, vendor selection, data retention, accuracy checks, and human approval gates.
• Move pilots into durable production processes with documentation, exception handling, monitoring, training, assigned owners, and measurable results.
• Build lightweight reporting on workflow usage, quality, time saved, cost, and business outcomes; retire or refine automation that does not work.
• Run selected cross-functional initiatives on the CEO’s behalf, including growth projects, process redesign, and integration planning, from charter through measurable delivery.
• Partner with the People Team and department heads to establish clear roles, SMART goals, and productive leadership rhythms.
• Improve the quality of business reviews and dashboards using leading and lagging indicators rather than anecdotal updates.
• Draft internal communications and recommendations; obtain appropriate approvals before sending external messages or making sensitive changes.

Benefits

• Competitive package to be finalized by the CEO and People Team; company benefits and any incentive/equity eligibility will be confirmed during recruiting.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed