Chief of Staff, Internal AI Optimization

the COOL company

About The Position

The COOL company is looking for a Chief of Staff to support the CEO and the rest of the executive team. This role consists of leading special projects, assisting in the development of various areas of business, and acting as a liaison for the CEO as needed. A key focus of this role is driving 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.

Requirements

8–10 years in a role supporting executives and/or C-suites
Very 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
Must be able to work primarily between the hours of 9:30 AM - 6:30 PM ET
Must have a player/coach mentality, willing to both execute and lead
Ability to juggle multiple projects concurrently and set and meet deadlines
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

Nice To Haves

Demonstrated experience with AI tools, CRM platforms, and emerging technology

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
Serve as a key representative of the executive team both inside and outside of the company
Handle confidential information, write correspondence, and support the CEO and teams across global time zones
Coordinate travel and related logistics on behalf of the CEO
Lead & 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
Lead projects do internal AI optimizations across the company
Effectively integrate subsidiaries