Chief of Staff & AI Integration

the COOL company•Miami, FL

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 person will partner with the CTO, functional leaders, and the People Team, while preserving functional ownership and not acting as the CTO or independently committing the company to external actions. The role focuses first on deploying useful AI workflows that employees use, with measurable time savings, clearer decisions, stronger follow-through, and appropriate data-security controls. The Chief of Staff will establish repeatable operating practices across a global, fast-moving organization with businesses spanning media, creative AI, advertising technology, publisher monetization, and other growth initiatives. The position is full-time and reports to the Founder & CEO. Miami or New York is preferred, with regular in-person collaboration and travel as needed; the final arrangement is subject to approval. Compensation and benefits are competitive and will be finalized or 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, rather than only 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.
Personally executes and takes end-to-end ownership.
Provides transparent status reporting, candid feedback, and immediate escalation of issues.
Relentlessly improves systems and challenges inefficient defaults.
Treats colleagues as partners and designs workflows that help them succeed.
Calm under ambiguity, discreet, curious, resourceful, low-ego, and comfortable holding senior leaders accountable.

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, distinguishing 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, then prioritize AI 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 AI 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; refine or retire 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 business reviews and dashboards using leading and lagging indicators rather than anecdotal updates.
Draft internal communications and recommendations, and obtain appropriate approvals before sending external messages or making sensitive changes.