Chief of Staff & AI Integration

Join The COOL Company as the Chief of Staff & AI Integration, where you will work directly with the Founder & CEO to turn priorities into accountable execution and lead practical, secure AI adoption across the business. This role requires a high-trust, hands-on operator with experience in business operations, strategy, and automation/transformation roles. You will be responsible for CEO effectiveness and execution, AI integration and automation, and strategic projects and organizational leverage.

• Assurer l'efficacité et l'exécution du PDG en gérant le calendrier opérationnel stratégique, en convertissant les discussions en actions prioritaires et en suivant leur réalisation.
• Auditer les flux de travail à fort frottement dans divers départements, puis concevoir, prototyper et mettre en œuvre des flux de travail AI sécurisés.
• Diriger des initiatives transversales sélectionnées au nom du PDG, y compris des projets de croissance, de redéfinition des processus et de planification de l'intégration.

• Experience in advertising/media/MarTech is a plus, not a prerequisite
• A demonstrated record of shipping cross-functional changes and building reliable operating processes, not just advising on them
• High analytical rigor: able to define baselines, evaluate ROI, measure adoption, and investigate inaccurate or misleading outputs
• A strong command of CRM, spreadsheets, dashboards, project management, meeting intelligence, and structured documentation
• Personally executes and takes end-to-end ownership
• Relentlessly improves systems and challenges inefficient defaults
• 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
• 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
• Calm under ambiguity, discreet, curious, resourceful, low-ego, and comfortable holding senior leaders accountable
• 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 is strongly preferred
• Treats colleagues as partners and designs workflows that help them succeed
• Provides transparent status reporting and candid feedback, and escalates issues immediately