Chief of Staff & AI Integration Job Cincinnati area,Ohio USA,Business

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…