Chief of Staff & AI Integration

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

Benefits

• Health, Dental and Vision Insurance
• Annual Performance Bonus
• Paid Time Off
• 401k
• Flexible work schedule
• Company Holidays

• 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