Chief of Staff & AI Integration

The COOL company is a global leader in AI-powered advertising technology, helping brands, agencies, and publishers simplify advertising and amplify performance.

Powered by COOL AI, our intelligent platform unifies creative generation, media activation, optimization, and attribution into one continuously learning system. Instead of relying on fragmented tools and manual campaign management, COOL AI executes thousands of real-time micro-optimizations across search, social, display, video, and connected TV-helping customers launch faster, optimize continuously, and achieve stronger business outcomes.

Our innovation and growth have earned industry-wide recognition, including being named a 7-time recipient of the Inc. 5000 list of America's Fastest-Growing Private Companies, a 2-time Deloitte Technology Fast 500 honoree, recognized on Crain's New York Fast 50, honored by the Digiday Media Awards for helping modernize digital media, and named one of Adweek's Top 10 Fastest Growing Solution Providers globally.

We're building the future of advertising, where every signal becomes intelligence and every optimization drives performance. As we continue to grow globally, we're looking for curious, ambitious people who want to work with cutting-edge AI technology, solve complex challenges, and help redefine what's possible in modern advertising.

The COOL Company is seeking a Chief of Staff & AI Integration to work directly with the Founder & CEO. This is a high-trust, hands-on operator who turns CEO priorities into accountable execution while leading practical, secure AI adoption across our businesses. The role sits at the intersection of executive operations, strategic projects, data, technology, and change management.

You will translate decisions into clear owners and deadlines, remove cross-functional bottlenecks, design and deploy AI-enabled workflows, and demonstrate their business impact. You will partner with the CTO, functional leaders, and the People Team; you will not replace functional ownership, act as the CTO, or independently commit the company to external actions.

We operate across media, creative AI, advertising technology, publisher monetization, and other growth initiatives. With global teams, frequent commercial opportunities, and a fast-moving CEO, the opportunity is to build a repeatable operating system that gets important work done faster, with fewer handoffs and better visibility.

The first priority is implementing useful AI—not producing slide decks about AI. Success means deployed workflows that employees actually use, measurable hours saved, clearer decisions, better follow-through, and strong data-security controls.

• Own the CEO's strategic operating cadence: 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; 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; push for decisions without creating unnecessary meetings.

• Audit high-friction workflows across Sales, Account Management, Marketing, Product, Engineering, Finance, People, and Operations, then 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…