Chief of Staff & AI Integration

Insticator, Inc.; Ohio; Sur place; USD 140 000 - 220 000; Plein temps

Avantages offerts par ce poste

Health Insurance

Annual Bonus

Paid Time Off

401k

Company Holidays

Flexible Schedule

Résumé du poste

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.

Responsabilités

• 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.

Connaissances

Executive operations

AI integration

Change management

Stakeholder leadership

Project management

Analytical rigor

CRM & dashboards

Outils

CRM systems

Spreadsheets

Workflow automation

Description du poste

• 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
• Company Holidays
• Flexible work schedule

Experience in advertising/media/MarTech is a plus, not a prerequisiteA demonstrated record of shipping cross-functional changes and building reliable operating processes, not just advising on themHigh analytical rigor: able to define baselines, evaluate ROI, measure adoption, and investigate inaccurate or misleading outputsA strong command of CRM, spreadsheets, dashboards, project management, meeting intelligence, and structured documentationPersonally executes and takes end-to-end ownershipRelentlessly improves systems and challenges inefficient defaultsHands-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 implementationsExceptional written communication, project management, prioritization, stakeholder leadership, and executive judgmentSound security and confidentiality instincts; understands human-in-the-loop approvals and sensitive-data handlingCalm under ambiguity, discreet, curious, resourceful, low-ego, and comfortable holding senior leaders accountable6+ 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 preferredTreats colleagues as partners and designs workflows that help them succeedProvides transparent status reporting and candid feedback, and escalates issues immediately