Chief of Staff & AI Integration

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 sits at the intersection of executive operations, strategic projects, data, technology, and change management. You will be responsible for CEO effectiveness and execution, AI integration and automation, and strategic projects and organizational leverage.

Responsibilities

• Success in this role means deployed workflows that employees actually use, measurable hours saved, clearer decisions, better follow-through, and strong data-security controls.
• 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 friction élevée 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.
• 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
• Treats colleagues as partners and designs workflows that help them succeed

Requirements

• 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

Preferred

• Experience in advertising/media/MarTech is a plus, not a prerequisite

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

Provides transparent status reporting and candid feedback, and escalates issues immediately