Chief of Staff for AI-Driven Operations

Insticator, Inc.; Ohio; On-site; USD 140,000 - 220,000; Full time

Benefits offered by this job

Health Insurance

Annual Bonus

Paid Time Off

401k

Company Holidays

Flexible Schedule

Job summary

The COOL Company is seeking a Chief of Staff & AI Integration to collaborate directly with the Founder & CEO. This high-trust, hands-on role turns CEO priorities into accountable execution while leading practical, secure AI adoption across our businesses.

You will partner with the CTO, functional leaders, and the People Team; you will not replace ownership or bind the company to external actions. Responsibilities include owning the CEO’s cadence, converting discussions into action, and building

Qualifications

• Experience driving cross-functional initiatives at senior levels.
• Ability to translate CEO priorities into actionable plans.
• Strong data-driven decision making and governance.

Responsibilities

• Own the CEO’s strategic operating cadence with priorities, follow-ups, meetings, decisions, and status updates.
• Convert CEO discussions into a prioritized action register with owners, deadlines, dependencies, escalations.
• Prepare concise executive briefs using CRM, meetings, and project systems; separate facts, assumptions, and recommendations.
• Identify and surface missed commitments and risks; push for timely decisions.
• Audit AI-enabled workflows across departments; prioritize high-impact use cases.
• Design, prototype, and implement secure AI workflows with approved tools and integrations.
• Collaborate with CTO and security owners on access, privacy, data retention, and approvals.
• Move pilots to production with documentation and measurable results.
• Build lightweight reporting on workflow usage and business outcomes.

Skills

Executive operations

AI integration

Change management

Stakeholder leadership

Project management

Analytical rigor

CRM & dashboards

Tools

CRM systems

Spreadsheets

Workflow automation

Job description

The COOL Company is seeking a Chief of Staff & AI Integration to collaborate directly with the Founder & CEO. This high-trust, hands-on role turns CEO priorities into accountable execution while leading practical, secure AI adoption across our businesses.

You will partner with the CTO, functional leaders, and the People Team; you will not replace ownership or bind the company to external actions. Responsibilities include owning the CEO’s cadence, converting discussions into action, and building