Chief of Staff, Internal AI Optimization
About The COOL Company
The COOL company believes in creating a win-win environment where everyone benefits. We are committed to ensuring users, publishers, franchisees, and advertisers all have a better experience and achieve more than they ever thought possible through our innovation, advanced AI, groundbreaking advertising technology, and teams of inspired experts.
COOL Media products include DCO & Creative Automation, a data-driven, creative ad server; Franchise & Multi-Location, a complete advertising management platform; Media & Attribution, a managed service solution; Publisher Experiences, a premier SSP and engagement platform; and Supply-Side Platform, delivering everything website and app publishers need to maximize their ad revenue.
Coming soon in 2026, COOL AI is a next-generation advertising platform that builds, buys, and optimizes digital ad campaigns faster and smarter using AI. It automates every step of the media journey—from generating ad creatives to launching campaigns and optimizing performance across channels like Google and Facebook.
Our Core Values at the COOL company are Creative, Open-minded, and Optimistic. We also believe in three truths that inform every decision we make and everything we do: Sleeves Up, 100% Viewability, and Be Defiantly Great.
Chief of Staff Role
The COOL company is seeking a Chief of Staff to support the CEO and the executive team. This role involves leading special projects, assisting in the development of various areas of business, and acting as a liaison for the CEO as needed.
Drive the company’s AI-forward strategy, including owning CRM systems powered by AI, integrating all Firefly company videos into an AI knowledge base to generate coaching outputs, and championing AI adoption across the organization.
Key Responsibilities
Serve as truest advisor to Zack and the executive team, providing strategic guidance and supporting key initiatives.
Lead special projects across business development, operations, and strategic growth initiatives.
Efficiently manage key processes and systems, including email inbox, Slack, and other tools, resulting in increased productivity and operational efficiency.
Execute strategic projects and tasks for the CEO such as decks, business plans, and longer-term initiatives.
Communicate daily with the CEO to optimize the planning and execution of his various commitments and responsibilities.
Manage all administrative duties for the CEO, including owning the calendar and scheduling all meetings and events.
Lead & organize quarterly team onsites.
Led & organize quarterly team onsites.
Act as a liaison between the CEO and other key stakeholders, both internal and external.
Own and manage the company CRM with AI integration, ensuring the system is continuously optimized, data is clean and actionable, and AI-driven insights are surfaced to the executive team.
Lead the initiative to ingest all Firefly company videos into an AI knowledge base, enabling intelligent coaching and insights to be automatically surfaced to the team.
Oversee the pipeline that transforms Firefly video content into personalized coaching outputs delivered via email and broader team communications.
Champion AI adoption across the organization from identifying opportunities to automating workflows, enhancing productivity, and embedding AI tooling into day-to-day operations.
Effectively integrate subsidiaries.
Qualifications
8–10 years in a role supporting executives and/or C-suites.
High EQ and people skills.
Creativity and open-mindedness.
Great project management skills.
Excellent written and verbal communication skills.
Ability to synthesize various viewpoints.
High empathy and ability to make team members feel heard and acknowledged.
Great listener and ability to absorb information.
Strategic thinking and problem-solving abilities.
Comfort with ambiguity and flexibility to adapt to changing priorities and deadlines.
Demonstrated experience with AI tools, CRM platforms, and emerging technology (strongly preferred).
Ability to manage and implement AI-driven workflows and communications systems.
Cultural Competencies
Able to work primarily between the hours of 9:30 AM - 6:30 PM ET.
Player/coach mentality, willing to both execute and lead.
Skilled at receiving and providing direct feedback.
Collaborative mindset and great teamwork skills.
Entrepreneurial & adaptable; great learning skills.
Curious, research-minded, data-informed.
Able to search for possible solutions and apply them.
Creative confidence.
Proactive communicator.
A sense of humor and a love of online culture.
Thrives in a start-up culture.