Chief of Staff & AI Integration

About the COOL company

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.

About the Role

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.

Challenges and Opportunities

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.

Responsibilities and Duties

CEO effectiveness and execution

• 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.

AI integration and automation

• 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 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.

Strategic projects and organizational leverage

• 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.

Qualifications

Professional Competencies

• 6+ years in high-ownership business operations, chief of staff, strategy and operations, consulting, product operations, or automation/transformation roles; meaningful time partnering with a founder or executive team strongly preferred.
• 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; able to prototype personally and work with engineers on production-grade implementations.
• Strong command of CRM, spreadsheets, dashboards, project management, meeting intelligence, and structured documentation. Experience in advertising/media/MarTech is a plus, not a prerequisite.
• High analytical rigor: can 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; understands human-in-the-loop approvals and sensitive-data handling.

Cultural Competencies

• Sleeves Up: personally executes and takes end-to-end ownership.
• 100% Viewability: transparent status reporting, candid feedback, and immediate escalation of issues.
• Be Defiantly Great: relentlessly improves systems and challenges inefficient defaults.
• Unconditional Empathy: 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.

What Success Looks Like

Within 90 days: a trusted CEO action and reporting cadence, at least five useful AI-enabled workflows in production, measurable usage and time-savings baselines, and demonstrably faster leadership follow-through. At six months: adoption is sustained across relevant teams and the measurable goals in the accompanying hiring scorecard are being met.

Role Details and Benefits

Reports to: Founder & CEO | Employment: Full-time | Level: Senior individual contributor / executive operator

Location: Miami or New York preferred, with regular in-person collaboration and travel as needed. Final arrangement subject to approval.

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